无溶剂及液相加成反应研究
|
摘要
环境科学的迅速发展迫切要求有机工作者发展出清洁、经济和环境较友好条件下的有机合成方法。其中,利用机械研磨方法进行的无溶剂有机化学反应非常具有发展潜力,近些年开始备受关注。本论文的主要工作是对机械研磨条件下的环加成反应和不对称加成反应进行研究,同时也对偶氮丁二酸酯的N-烷基化和N-芳基化反应进行了探讨,具体包括以下几方面内容:
1.采用机械研磨的方法成功实现了在溶剂条件下醋酸锰促进的1,3-环己二酮和达米酮对氮杂α,β-不饱和酮的自由基加成反应,改善了醋酸锰促进的反应必须在乙酸或其它强极性有机溶剂中进行并且醋酸锰需大大过量的缺点,同时产率也有很大的提高。值得注意的是,氮杂α,β-不饱和酮和1,3-环己二酮反应得到了不同于传统自由基加成反应的产物,因此我们认为该反应可能是首先经过了一步Michael加成反应,然后再进行自由基环加成得到了反式-2-吡啶甲酰基-3-芳基/烷基取代的二氢呋喃产物。我们认为醋酸锰在反应中起到了Lewis酸和自由基引发剂的双重作用。
2.采用机械研磨方法进行了连续的两步固相化学反应的研究:首先,在氢氧化钾和18-冠-6的作用下,端基炔和羰基化合物在机械研磨条件下反应可以高效地生成相应的炔醇化合物;其次,在四水合三氯化铟的催化作用下,生成的炔醇化合物和2-萘酚在机械研磨条件下环加成生成相应的萘并吡喃产物。该机械研磨的方法具有不需要使用有机溶剂,反应条件比较温和,后处理简单,产物产率高等优点;与之前常用的合成炔醇和萘并吡喃的方法相比有其自身的优越性,这也使得该方法成为合成这一类型化合物的潜在选择。
3.采用机械研磨方法研究了手性磷酸催化的吲哚和亚胺的固相不对称Friedel-Crafts反应,首先通过催化剂的筛选,发现3,3'-位1-萘酚取代的手性BINOL(联萘酚)磷酸具有最好的催化效果;然后在反应的载体、温度、吲哚的用量以及机械研磨反应的频率这几方面对反应的结果进行优化。在优化后的条件下,各种取代的吲哚和亚胺能够迅速进行反应,在很短的时间内高产率地得到了具有中等偏上ee值的加成产物。
4.研究了由β-羰基酮或β-酮酸酯与偶氮丁二酸二乙酯通过无溶剂直接加热来制备氮烷基取代肼衍生物的反应,利用该产物可以进一步制备α-氨基取代的二羰基化合物。该反应具有不使用任何催化剂、操作简单、后处理简便等优点。
5.在[Cu(OH)·TMEDA]_2Cl_2的催化作用下,各种芳硼酸都能和偶氮丁二酸酯进行氮芳基化反应,以很高的产率生成相应的肼类衍生物,甚至可以催化甲基硼酸和偶氮丁二酸二乙酯的氮甲基化反应。和其它的合成方法相比,该反应具有不需要进行氮气保护,催化剂[Cu(OH)·TMEDA]_2Cl_2对底物的适用范围广,反应时间短,催化效率高等优点。
For the stringent and growing environmental regulations,organic chemists are requested to develop clean,economical and environmental safer methodologies. Performing organic reactions with mechanochemical technique under solvent-free conditions is a very promising approach.The main work presented in this dissertation is about the investigation on cycloaddition reactions and asymmetric reaction carried out under mechanochemical conditions.And also,we studied the N-alkylation and N-arylation reaction of azodicarboxylate esters.
1.We have developed the synthesis of trans-2-acyl-3-aryl/alkyl-2,3,6,7-tetrahydro-4(5H)-benzofuranone derivatives through the radical reactions of 1-(pyridin-2-yl)-enones with 1,3-cyclohexanediones mediated by Mn(OAc)_3·2H_2O.The present solvent-free radical reactions were very efficient, affording the unexpected products in as high as 91%yield under our ball-milling conditions.More importantly,the reversed regioselectivity of 1-(pyridin-2-yl)-enones was uncovered for the first time.Mn(OAc)_3·2H_2O played the role both as an oxidant and as a Lewis acid,and thus altered the reaction pathway of 1-(pyridin-2-yl)-enones.
2.We have presented a practical method for the preparation of propargylic alcohols from terminal alkynes and carbonyl compounds promoted by KOH in the presence of 18-crown-6,and subsequent efficient cyclizations of propargylic alcohols with 2-naphthol catalyzed by InCl_3·4H_2O under the solvent-free ball-milling conditions.Ball milling exhibits its superiority over the reported methods in the preparation of propargylic alcohols and naphthopyran derivatives. The advantages of this procedure including avoidance of any solvent,mild condition,high yield,short reaction time and easy work-up procedure made the present method a convenient,effective and environmentally friendly one,which could serve as an attractive alternative to the traditional methodology.
3.Chiral phosphoric acid mediated,solvent-free asymmetric Fridel-Crafts reactions of indols and imines have been carried out under solid-state mechanochemical conditions.In which,3,3'-(1-naphthyl) substituted chiral phosphoric acid was found to possess the best catalytic ability.Some other aspects such as the reaction temperature,amount of indols and the frequency of ball milling were also investigated.Under the Optimized reaction conditions,the addition products could be obtained in a short time with high yield and moderate enantiomeric excess.
4.A simple and efficient method for the solvent-free synthesis of N-alkyl substituted hydrazines has been described.By direct thermal heating,N-alkylation reactions of 1,3-diketones andβ-keto esters with diethyl azodicarboxylate ester proceeded well in excellent yields.The products could serve as substrates for further preparation ofα-amino-1,3-dicarbonyl compounds.This method provided several advantages such as no usage of any solvent,being environmentally friendly, simple work-up procedure and high yields.
5.We have developed an efficient catalytic system for preparing a variety of aryl-substituted hydrazines in up to 99%yield through the coupling of arylboronic acids with azodicarboxylate esters in the presence of the easily available catalyst[Cu(OH)·TMEDA]_2Cl_2.This N-arylation reaction of azodicarboxylate esters did not require protection with inert atmosphere because oxygen was not involved in the reaction.Moreover,the[Cu(OH)·TMEDA]_2Cl_2-catalyzed coupling reaction exhibited excellent selectivity of arylboronic acids for the N-arylation reaction over the homocoupling reaction.
1.采用机械研磨的方法成功实现了在溶剂条件下醋酸锰促进的1,3-环己二酮和达米酮对氮杂α,β-不饱和酮的自由基加成反应,改善了醋酸锰促进的反应必须在乙酸或其它强极性有机溶剂中进行并且醋酸锰需大大过量的缺点,同时产率也有很大的提高。值得注意的是,氮杂α,β-不饱和酮和1,3-环己二酮反应得到了不同于传统自由基加成反应的产物,因此我们认为该反应可能是首先经过了一步Michael加成反应,然后再进行自由基环加成得到了反式-2-吡啶甲酰基-3-芳基/烷基取代的二氢呋喃产物。我们认为醋酸锰在反应中起到了Lewis酸和自由基引发剂的双重作用。
2.采用机械研磨方法进行了连续的两步固相化学反应的研究:首先,在氢氧化钾和18-冠-6的作用下,端基炔和羰基化合物在机械研磨条件下反应可以高效地生成相应的炔醇化合物;其次,在四水合三氯化铟的催化作用下,生成的炔醇化合物和2-萘酚在机械研磨条件下环加成生成相应的萘并吡喃产物。该机械研磨的方法具有不需要使用有机溶剂,反应条件比较温和,后处理简单,产物产率高等优点;与之前常用的合成炔醇和萘并吡喃的方法相比有其自身的优越性,这也使得该方法成为合成这一类型化合物的潜在选择。
3.采用机械研磨方法研究了手性磷酸催化的吲哚和亚胺的固相不对称Friedel-Crafts反应,首先通过催化剂的筛选,发现3,3'-位1-萘酚取代的手性BINOL(联萘酚)磷酸具有最好的催化效果;然后在反应的载体、温度、吲哚的用量以及机械研磨反应的频率这几方面对反应的结果进行优化。在优化后的条件下,各种取代的吲哚和亚胺能够迅速进行反应,在很短的时间内高产率地得到了具有中等偏上ee值的加成产物。
4.研究了由β-羰基酮或β-酮酸酯与偶氮丁二酸二乙酯通过无溶剂直接加热来制备氮烷基取代肼衍生物的反应,利用该产物可以进一步制备α-氨基取代的二羰基化合物。该反应具有不使用任何催化剂、操作简单、后处理简便等优点。
5.在[Cu(OH)·TMEDA]_2Cl_2的催化作用下,各种芳硼酸都能和偶氮丁二酸酯进行氮芳基化反应,以很高的产率生成相应的肼类衍生物,甚至可以催化甲基硼酸和偶氮丁二酸二乙酯的氮甲基化反应。和其它的合成方法相比,该反应具有不需要进行氮气保护,催化剂[Cu(OH)·TMEDA]_2Cl_2对底物的适用范围广,反应时间短,催化效率高等优点。
For the stringent and growing environmental regulations,organic chemists are requested to develop clean,economical and environmental safer methodologies. Performing organic reactions with mechanochemical technique under solvent-free conditions is a very promising approach.The main work presented in this dissertation is about the investigation on cycloaddition reactions and asymmetric reaction carried out under mechanochemical conditions.And also,we studied the N-alkylation and N-arylation reaction of azodicarboxylate esters.
1.We have developed the synthesis of trans-2-acyl-3-aryl/alkyl-2,3,6,7-tetrahydro-4(5H)-benzofuranone derivatives through the radical reactions of 1-(pyridin-2-yl)-enones with 1,3-cyclohexanediones mediated by Mn(OAc)_3·2H_2O.The present solvent-free radical reactions were very efficient, affording the unexpected products in as high as 91%yield under our ball-milling conditions.More importantly,the reversed regioselectivity of 1-(pyridin-2-yl)-enones was uncovered for the first time.Mn(OAc)_3·2H_2O played the role both as an oxidant and as a Lewis acid,and thus altered the reaction pathway of 1-(pyridin-2-yl)-enones.
2.We have presented a practical method for the preparation of propargylic alcohols from terminal alkynes and carbonyl compounds promoted by KOH in the presence of 18-crown-6,and subsequent efficient cyclizations of propargylic alcohols with 2-naphthol catalyzed by InCl_3·4H_2O under the solvent-free ball-milling conditions.Ball milling exhibits its superiority over the reported methods in the preparation of propargylic alcohols and naphthopyran derivatives. The advantages of this procedure including avoidance of any solvent,mild condition,high yield,short reaction time and easy work-up procedure made the present method a convenient,effective and environmentally friendly one,which could serve as an attractive alternative to the traditional methodology.
3.Chiral phosphoric acid mediated,solvent-free asymmetric Fridel-Crafts reactions of indols and imines have been carried out under solid-state mechanochemical conditions.In which,3,3'-(1-naphthyl) substituted chiral phosphoric acid was found to possess the best catalytic ability.Some other aspects such as the reaction temperature,amount of indols and the frequency of ball milling were also investigated.Under the Optimized reaction conditions,the addition products could be obtained in a short time with high yield and moderate enantiomeric excess.
4.A simple and efficient method for the solvent-free synthesis of N-alkyl substituted hydrazines has been described.By direct thermal heating,N-alkylation reactions of 1,3-diketones andβ-keto esters with diethyl azodicarboxylate ester proceeded well in excellent yields.The products could serve as substrates for further preparation ofα-amino-1,3-dicarbonyl compounds.This method provided several advantages such as no usage of any solvent,being environmentally friendly, simple work-up procedure and high yields.
5.We have developed an efficient catalytic system for preparing a variety of aryl-substituted hydrazines in up to 99%yield through the coupling of arylboronic acids with azodicarboxylate esters in the presence of the easily available catalyst[Cu(OH)·TMEDA]_2Cl_2.This N-arylation reaction of azodicarboxylate esters did not require protection with inert atmosphere because oxygen was not involved in the reaction.Moreover,the[Cu(OH)·TMEDA]_2Cl_2-catalyzed coupling reaction exhibited excellent selectivity of arylboronic acids for the N-arylation reaction over the homocoupling reaction.
引文
[1](a)Anastas,P.T.;Warner,J.C.绿色化学:理论和应用.李朝军,王东译 2002;
(b)Anastas,P.T.;Warner,J.C.Green Chemistry.Frontiers in Beijing Chemical Synthesis and Processes;Oxford:Oxford Univ.Press,1998.
[2]Anastas,P.T.;Warner,J.C.Green Chemistry:Thery and Practical;New York:Oxford Univ.Press,1998.
[3]Winterton,N.Green Chem.2001,6,G73.
[4]Trost,B.M.Science 1991,254,1471.
[5]Dzyuba,S.V.;Bartsch,R.A.Angew Chem.,Int.Ed.2003,42,148.
[6](a) Doll,K.M.;Ethan,S.Z.Green Chem.2008,10,712;
(b) Walsh,P.J.;Li,H.M.;de Parrodi,C.A.Chem.Rev.2007,107,2503.
[7](a) Deng,G.J.;Fan,Q.H.;Chen,X.M.et al.Chem.Commun.2002,1570;
(b) Tang,W.J.;Yang,N.F.;Yi,B.Chem.Commun.2004,1378;
(c) Heldebrant,D.J.;Jessop,P.G.J.Am.Chem.Soc.2003,125,5600.
[8]Peters K.Mechanochemische Peaktionen.Frankfurt,1962.
[9]Heinicke G.Tribochemistry.Berlin:Akademie Verlag,1984.
[10]Garay,A.L.;Pichon,A.;James,S.L.Chem.Soc.Rev.2007,36,846.
[11]Lyakhov,N.;Grigodeva,T.;Barinova,A.;Lomayeva,S.;Yelsukov,E.;Ulyanov,A.J.Mater.Sci.2004,39,5421.
[12](a) Rodriguez,B.;Bruckmann,A.;Rantanen,T.;Bolm,C.Adv.Synth.Catal.2007,349,2213;
(b) Mack,J.;Fulmer,D.;Stofel,S.;Santos,N.Green Chem.2007,9,1041;
(c) Kaupp,G.Top.Curr.Chem.2005,254,95;
(d) Balema,V.P.;Wiench,J.W.;Pruski M.;Pecharsky,V.K.J.Am.Chem.Soc.2002,124,6244;
(e) Toda,F.Acc.Chem.Res.1995,28,480.
[13]Beyer,M.K.;Clausen-Schaumann,H.Chem.Rev.2005,105,2921.
[14]Delogu,F.;Orru,R.;Can,G.Chem.Eng.Sci.2003,58,815.
[15](a) Urakaev,F.K.;Boldyrev,V.V.Powder Technology 2000,107,93;
(b) Urakaev,F.K.;Boldyrev,V.V.Powder Technology 2000,107,197.
[16](a) Gao,J.;Wang,G.-W.J.Org.Chem.2008,73,2955;
(b) Wu,X.-L.;Xia,J.-J.;Wang,G.-W.Org.Biomol.Chem.2008,6,548;
(c) Wang,G.-W.;Wu,X.-L.Adv.Synth.Catal.2007,349, 1977;
(d) Zhang,Z.;Gao,J.;Xia,J.-J.;Wang,G.-W.Org.Biomol.Chem.2005,3,1617;
(e)Zhang,Z.;Wang,G.-W.;Miao,C.-B.;Dong,Y.-W.;Shen,Y.-B.Chem.Commun.2004,1832;
(f) Zhang,Z.;Dong,Y.-W.;Wang,G.-W.;Komatsu,K.Synlett 2004,61;
(g) Wang,G.-W.;Liu,L.Chinese Chin.Lett.2004,15,587;
(h) Zhang,Z.;Dong,Y.-W.;Wang,G.-W.Chem.Lett.2004,33,168.
[17](a) For a review,see:Wang,G.-W."Fullerene Mechanochemistry",in:Encyclopedia of Nanoscience and Nanotechnology,Vol.3,(Ed.:H.S.Nalwa),American Scientific Publishers,Stevenson Ranch,2004,pp 557;
(b) Chen,Z.-X.;Zhu,B.;Wang,G.-W.Lett.Org.Chem.2008,5,65;
(c) Cheng,X.;Wang,G.-W.;Murata,Y.;Komatsu,K.Chin.Chem.Lett.2005,16,1327;
(d) Wang,G.-W.;Chen,Z.-X.;Murata,Y.;Komatsu,K.Tetrahedron 2005,61,4851;
(e)Li,Y.-J.;Peng,R.-F.;Liu,Y.-C.;Wang,G.-W.Chin.Chem.Lett.2004,15,1265;
(f) Peng,R.-F.;Wang,G.-W.;Shen,Y.-B.;Li,Y.-J.;Zhang,T.-H.;Liu,Y.-C.;Murata Y.;Komatsu,K.Synth.Commun.2004,34,1309;
(g) Zhang,T.-H.;Wang,G.-W.;Lu,P.;Li,Y.-J.;Peng,R.-F.;Liu,Y.-C.;Murata,Y.;Komatsu,K.Org.Biomol.Chem.2004,2,1698;
(h) Zhang,T.-H.;Li,Y.-J.Peng,R.-F.;Lu,P.;Chen,Z.-X.;Wang,G.-W.Chinese J.Org.Chem.2003,23,392;
(i)Wang,G.-W.;Zhang,T.-H.;Li,Y.-J.;Lu,P.;Zhan,H.;Liu,Y.-C.;Murata,Y.;Komatsu,K.Tetrahedron Lett.2003,44,4407;
(j) Wang,G.-W.;Zhang,T.-H.;Hao,E.-H.;Jiao,L.-J.;Murata,Y.;Komatsu,K.Tetrahedron 2003,59,55.
[18]Rodriguez,B.;Rantanen T.;Bolm,C.Angew.Chem.,Int.Ed.2006,45,6924.
[19](a) Rodriguez,B.;Bruckmann,A.;Bolm,C.Chem.Eur.J.2007,13,4710;
(b) Xiong,H.;Wu,H.;Xu,G.;Yang,Y.Biochem.Eng.J.2008,138,258;
(c) Guillena,G.;del Carmen Hita,M.;Najera,C.Viozquez,S.F.J.Org.Chem.2008,73,5933;
(d) Rantanen,T.;Schiffers,I.;Bolm,C.Orgo Process Res.Dev.2007,11,592;
(e) Guillena,G.;del Carmen Hita,M.;Najera,C.Viozquez,S.F.Tetrahedron:Asymmetry 2007,18,2300.
[1]Badanyan,S.O.;Melikyan,G.G.;Mkrtchyan,D.A.Russ.Chem.Rev.1989,58,286(Usp. Khim., 1989, 55, 475).
[2] Melikyan, G. G. Synthesis 1993, 833.
[3] Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519.
[4] Snider, B. B. Chem. Rev. 1996, 96, 339.
[5] Heiba, E. I.; Dessau, R. M.; Koehl, W. J. J. Am. Chem. Soc. 1968, 90, 5905.
[6] Bush, J. B.; Finkbeiner, H. J. Am. Chem. Soc. 1968, 90, 5903.
[7] Heiba, E. I.; Dessau, R. ML, J. Org. Chem. 1974, 39, 3456.
[8] (a) Heiba, E. I.; Dessau, R. M.; Koehl, W. J. J. Am. Chem. Soc. 1968, 90, 2706; (b) Heiba, E.I.; Dessau, R. M.; Koehl, W. J. J. Am. Chem. Soc. 1969, 91, 138; (c) Heiba, E. I.; Dessau, R.M. Discuss. Faraday Soc. 1968, 46, 189; (d) Heiba, E. I.; Dessau, R. M. J. Am. Chem. Soc.1971, 93, 524; (e) Heiba, E. I.; Dessau, R. M.; Rodewald, P. G. J. Am. Chem. Soc. 1974, 96,7977; (f) Heiba, E. I.; Dessau, R. M.; Williams, A. L.; Rodewald, P. G. Org. Synth. 1983, 61,22.
[9] Bush, J. B.; Finkbeiner, H. J. Am. Chem. Soc. 1968, 90, 5903.
[10]Ploeg, R. E. V.; Korte, R. W.; Kooyman, E. C. J. Catal. 1968,10, 52.
[11](a) Nikishin, G. I.; Vinogradov, M. G.; Il'ina, G. P. Synthesis 1972, 376; (b) Nikishin, G. I.;Vinogradov, M. G.; Il'ina G. P. J. Org. Chem. 1972, 8, 1422; (c) Nikishin, G. I.; Vinogradov,M. G.; Fedorova, T. M. J. Chem. Soc, Chem. Commun. 1973, 693; (d) Vinogradov, M. G.;Fedorova, T. M.; Nikishin, G. I. J. Org. Chem. 1976, 12, 1183; (e) Vinogradov, M. G.;Verenchikov, S. P.; Nikishin, G. I. J. Org. Chem. 1976,12, 2245.
[12](a) McQuillin, F. J.; Wood, M. J. Chem. Res., Synop. 1977, 61; (b) McQuillin, F. J.; Wood, M.J. Chem. Soc, Perkin Trans. 1 1976, 1762.
[13](a) Fristad, W. E.; Peterson, J. R. J. Org. Chem. 1985, 50, 10; (b) Fristad, W. E.; Hershberger,S. S. J. Org. Chem. 1985, 50, 1026; (c) Fristad, W. E.; Peterson, J. R.; Ernst, A. B. J. Org.Chem. 1985, 50, 3143; (d) Fristad, W. E.; Brandvold, T. A.; Peterson, J.; Thompson, S. R. J.Org. Chem. 1985, 50, 3647; (e) Fristad, W. E.; Ernst, A. B. Tetrahedron Lett. 1985, 26, 3761;(f) Yann, F. Z.; Trost, M. K.; Fristad, W. E. Tetrahedron Lett. 1987. 28, 1493.
[14](a) Corey, E. J.; Kang, M.-C. J. Am. Chem. Soc. 1984,106, 5384; (b) Corey, E. J.; Gross, A.W. Tetrahedron Lett. 1985, 26, 4291.
[15](a) Corey, E. J.; Ghosh, A. K. Chem. Lett. 1987, 223; (b) Kochi, J. K.; Davis, D. D. J. Am.Chem. Soc. 1964, 86, 5264; (c) Davis, D. D.; Kochi, J. K. Nature 1964, 202, 690; (d) Kochi, J.K.; Mocadlo, P. E. J. Am. Chem. Soc. 1966, 88, 4094; (e) Kochi, J. K.; Mocadlo, P. E. J. Org.Chem. 1965, 30, 1134; (f) Kochi J. K.; Powers, S. W. J. Am. Chem. Soc. 1970, 92, 137; (g)Krusic, P. J.; Fagan, P. J.; San Filippo, J. S. J. Am. Chem. Soc. 1977, 99, 250; (h) Maillard, B.; Forrest,D.;Ingold,K.U.J.Am.Chem.Soc.1976,98,7024;
(i) Kochi,J.K.Acc.Chem.Res.1974,7,351;
(j) Inaba,S.;Ojima,I.Tetrahedron Lett.1977,18,2009.
[16]Tanyeli,C.;Ozdemirhan,D.Tetrahedron Lett.2003,44,7311.
[17]Zhu,Y.;Bahnmueller,S.;Hosmane,N.S.;Maguire,J.A.Chem.Lett.2003,32,730.
[18]Barr,G.;Parsons,A.F.;Yhomas,C.B.Org.Biomol.Chem.2003,1,373.
[19]Artis,D.R.;Cho,I.S.;Muchowski,J.M.Can.J.Chem.1992,70,1838.
[20]Rahman,M.T.;Nishino,H.Tetrahedron 2003,59,8383.
[21]Dimir,A.S.;Reis,O.;Ozgul-Karaaslan,E.J.Chem.Soc.,Perkin Trans.1 2001,3042.
[22]Demir,A.S.;Reis,O.;Emrullahoglu,M.Tetrahedron 2002,58,8055.
[23]Demir,A.S.;Reis,O.;Emrullahoglu,M.J.Org.Chem.2003,68,578.
[24]Chikaoka,S.;Toyao,A.;Ogasawara,M.;Tamura,T.;Ishibashi,H.J.Org.Chem.2003,68,312.
[25]Thomas,N.F.;Lee,J.R.;Paraidathathu,T.;Weber,J.F.F.;Awang,K.Tetrahedron Lett.2002,43,3151.
[26]Snider,B.B.;Che,Q.Heterocycles 2004,62,325.
[27]Yilmaz,M.;Uzunalioglu,N.;Pekel,A.T.Tetrahedron 2005,61,8860.
[28]Alagoz,O.;Yilmaz,M.;Pekel,A.Synth.Commum.2006,36,1005.
[29]Fu,W.-J.;Huang,X.J.Organomet.Chem.2007,692,740.
[30]Rahman,M.T.;Nishino,H.Org.Lett.2003,5,2887.
[31]Kumabe,R.;Nishino,H.Tetrahedron Lett.2004,45,703.
[32]Wang,G.-W.;Zhang,T.-H.;Cheng,X.;Wang,F.Org.Biomol.Chem.2004,2,1160.
[33]Wang,G.-W.;Fa-Bao li Org.Biomol.Chem.2005,3,794.
[34]Wang,G.-W.;Yang,H.T.;Miao,C.B.;Xu,Y.;Liu,F.Org.Biomol.Chem.2006,4,2595.
[35]Chen,Z.-X.;Wang,G.-W.J.Org.Chem.2005,70,2380.
[36]Wang,G.-W.;Li,F.-B.;Zhang T.-H.Org.Lett.2006,8,1355.
[37]Bar,G.;Parson,A.F.;Thomas,C.B.Chem.Commum.2001,1350.
[38]Liao,Y.-Y.;Wu,Y.-L.;Chuang,C.-P.Tetrahedron 2003,59,3511.
[39]Sung,K.;Wang,Y.Y.J.Org.Chem.2003,68,2771.
[40]Ryu,I.;Alper,H.J.Am.Chem.Soc.1993,115,7543.
[41]Ji,N.;Rosen,B.M.;Myers,A.G.Org.Lett.2004,6,4551.
[42]Hulcoop,D.G.;Burton,J.W.Chem.Commum.2005,4687.
[43]Demir,A.S.;Caliskan,Z.A.;Aydin,A.E.;Biter,I.Tetrahedron:Asymmetry 2006,17,786.
[44]Demir,A.S.;Reis,O.;Igdir,C.Tetrahedron 2004,60,3427.
[45]Demir,A.S.;Sesenoglu,O.Org.Lett.2002,4,2021.
[46]Fristad, W. E.; Brandvold, T. A.; Peterson, J. R.; Thompson, S. R. J. Org. Chem. 1985, 50,3647.
[47]Snider, B. B.; Duvall, J. R. Org. Lett. 2004, 6, 1265.
[48]Nguyen, V.-H.; Nishino, H.; Kajikawa, K. Tetrahedron 1998, 54, 11445.
[49]Mu, X.-J.; Zou, J.-P.; Zeng, R.-S.; Wu, J.-C. Tetrahedron Lett. 2005, 46, 4345.
[50]Tayama, O.; Nakano, A.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2004, 69, 5494.
[51]Takashi, K.; Nakano, A.; Sakaguchi, S.; Ishii, Y. Org. Lett. 2006, 8, 407.
[52]Varma, R. S.; Kumar, D. Tetrahedron Lett. 1999, 40, 21.
[53]Shing, T. K. M.; Yeung, Y.-Y.; Su, P. L. Org. Lett. 2006,8, 3149.
[54]Snider, B. B.; Zhang, Q. J. Org. Chem., 1993, 55, 3185.
[55]Snider, B. B.; McCarthy, B. A. J. Org. Chem., 1993, 58,6217.
[56]Zhang, Q.; Mohan, R. M.; Cook, L.; Kazanis, S.; Peisach, D.; Foxman, B. M.; Snider, B. B. J.Org. Chem., 1993,55,7640.
[57]Vo, N. H.; Snider, B. B. J. Org. Chem., 1994, 59, 5419.
[58]Snider, B. B.; O'Neil, S. Tetrahedron, 1995, 51, 12983.
[59](a)Garzino, F.; Meou, A.; Brun, P. Tetrahedron lett. 2000, 41, 9803; (b) Garzino, F.; Meou, A.;Brun, P. Eur. J. Org. Chem. 2003, 1410; (c) Martinet, S.; Meou, A.; Brun, P.; Magn. Reson.Chem. 2007, 45, 182; (d) Garzino, F.; Meou, A.; Brun, P. Helv. Chim. Ada 2002, 55, 1989; (e) Garzino, F.; Meou, A.; Brun, P. Tetrahedron Lett. 2002, 43, 5049.
[60](a) Meou, A.; Lamarque, L.; Brun, P. Tetrahedron lett. 2002, 43, 5301. (b) Lamarque, L.;Meou, A.; Brun, P. Tetrahedron lett. 1998, 39, 8283.
[61]Shanmugam, P.; Kumar, K. H.; Perumal, P. T. J. Heterocycl. Chem. 2007, 44, 827.
[62]Zhang, Z.; Wang, G.-W.; Miao, C.-B.; Dong, Y.-W.; Shen, Y.-B. Chem. Commun. 2004, 1832.
[63](a) Yang, Z.; Fan, M.; Mu, R.; Liu, W.; Liang, Y. Tetrahedron 2005, 61, 9140. (b) Cao, W.;Chen, G.; Chen, J.; Chen, R. Synth. Commun. 2005, 35, 527; (c) Pohmakotr, M.; Issaree, A.;Sampaongoen, L.; Tuchinda, P.; Reutrakul, V. Tetrahedron Lett. 2003, 44, 7937.
[64](a) Zhang, W.; Huo, C. D.; Liu, Z. G.; Liu, Z. L. Chin. Chem. Lett. 2004,15, 389; (b) Roy, S.C.; Mandal, P. K. Tetrahedron 1996, 52,2193.
[65] (a) Cossy, J.; Bouzide, A.; Leblanc, C. J. Org. Chem. 2000, 65, 7257. (b) Wang, G.-W.; Li,F.-B. Org. Biomol. Chem. 2005, 3, 794.
[66](a) Milios, C. J.; Stamatatos, T. C.; Kyritsis, P.; Terzis, A.; Raptopoulou, C. P.; Vicente, R.;Escuer, A.; Perlepes, S. P. Eur. J. Inorg. Chem. 2004, 2885. (b) Friestad, G. K. Eur. J. Org.Chem. 2005, 3157. (c) Sugiura, M.; Kobayashi, S. Angew. Chem., Int. Ed. 2005, 44, 5176.
[1]For a review,see:Cozzi,P.G.;Hilgraf,R.;Zimmermann,N.Eur.J.Org.Chem.2004,4095.
[2]Brandsma,L.Preparative Acetylenic Chemistry;Elsevier:Amsterdam,1988;p79.
[3]Eaton,P.E.;Srikrishna,A.;Uggeri,F.J.Org.Chem.1984,49,1728.
[4]Viehe,H.G.;Reinstein,M.Chem.Ber.1962,95,2557.
[5]Fisch,A.;Coisne,J.M.;Figeys,H.P.Synthesis 1982,211.
[6](a) Evans,J.C.;Goralski,C.T.;Hasha,D.L.J.Org.Chem.1992,57,2941;
(b) Brown,H.C.;Molander,G.A.;Singh,S.M.;Racherla,U.S.J.Org.Chem.1985,50,1577.
[7]Ahn,J.H.;Joung,M.J.;Yoon,N.M.J.Org.Chem.1995,60,6173.
[8]Imamoto,T.;Sugiura,Y.;Takiyama,N.Tetrahedron Lett.1984,25,4233.
[9]Hirao,T.;Misu,D.;Agawa,T.Tetrahedron Lett.1986,27,933.
[10]Yamaguchi,M.;Hayashi,A.;Minami,T.J.Org.Chem.1991,56,4091.
[11]Yamaguchi,M.;Hayashi,A.;Hirama,M.Chem.Lett.1992,2479.
[12]Han,Y.;Huang,Y.-Z.Tetrahedron Lett.1995,36,7277.
[13]Jiang,B.;Si,Y.-G.Tetrahedron Lett.2002,43,8323.
[14]Sakai,N.;Hirasawa,M.;Konakahara,T.Tetrahedron Lett.2003,44,4171.
[15]Takita,R.;Fukuta,Y.;Tsuji,R.;Ohshima,T.;Shibasaki,M.Org.Lett.2005,7,1363.
[16]Fassler,R.;Tomooka,C.S.;Frantz,D.E.;Carreira,E.M.PNAS 2004,101,5843.
[17]Babler,J.H.;Liptak,V.P.;Phan,N.J.Org.Chem.1996,61,416.
[18]Tzalis,D.;Knochel,P.Angew.Chem.,Int.Ed.1999,38,1463.
[19]Ishikawa,T.;Mizuta,T.;Hagiwara,K.;Aikawa,T.;Kudo,T.;Saito,S.J.Org.Chem.2003,68,3702.
[20]Imahori,T.;Hori,C.;Kondo,Y.Adv.Synth.Catal.2004,346,1090.
[21](a) Kuo,D.L.U.S.Patent 5 919 992,1999;
(b) Patents are cited by Tedeschi,R.J.;Casey,A.W.;Clark,G.S.,Jr.;Huckel,R.W.;Kindley,L.M.;Russell,J.P.J.Org.Chem.1963,28,1740.
[22](a) Moorthy,J.N.;Venkatakrishnan,P.;Samanta,S.;Kumar,D.K.Org.Lett.2007,9,919;
(b)Frigoli,M.;Mehl,G.H.Angew.Chem.,Int.Ed.2005,44,5048;
(c) Queiroz,M.-J.R.P.;Abreu,A.S.;Ferreira,P.M.T.;Oliveira,M.M.;Dubest,R.;Aubard,J.;Samat,A.Org.Lett.2005,7,4811;
(d) Kaneko,T.;Akutsu,H.;Yamada,J.-I.;Nakatsuji,S.Org.Lett.2003,5,2127;
(e) Samat,A.;Lokshin,V.;Chamontin,K.;Levi,D.;Pepe,G.;Guglielmetti,R.Tetrahedron 2001,57,7349;
(f) Gabbutt,C.D.;Hepworth,J.D.;Heron,B.M.;Partington,S.M.Dyes and Pigments 2000,47,73;
(g) Stauffer,M.T.;Knowles,D.B.;Brennan,C.;Funderburk,L.;Lin,F.-T.;Weber,S.G.Chem.Commun.1997,287.
[23]Bigi,F.;Carloni,S.;Maggi,R.;Muchetti,C.;Sartori,G.J.Org.Chem.1997,62,7024.
[24]Nishibayashi,Y.;Inada,Y.;Hidai,M.;Uemura,S.J.Am.Chem.Soc.2002,124,7900.
[25]Gabbutt,C.D.;Heron,B.M.;Instone,A.C.;Thomas,D.A.;Partington,S.M.;Hursthouse,M.B.;Gelbrich,T.Eur J.Org.Chem.2003,1220.
[26]Zhao,W.;Carreira,E.M.Org.Lett.2003,5,4153.
[27]Gabbutt,C.D.;Heron,B.M.;Instone,A.C.;Horton,P.N.;Hursthouse,M.B.Tetrahedron 2005,61,463.
[28]Baldoumi,V.;Gautam,D.R.;Litinas,K.E.;Nicolaides,D.N.Tetrahedron 2006,62,8016.
[29]Zhao,W.;Carreira,E.M.Org.Lett.2006,8,99.
[30]Worlikar,S.A.;Kesharwani,T.;Yao,T.;Larock,R.C.J.Org.Chem.2007,72,1347.
[31]Tanaka,K.;Aoki,H.;Hosomi,H.;Ohba,S.Org.Lett.2000,2,2133.
[32](a) Rodriguez,B.;Bruckmann,A.;Rantanen,T.;Bolm,C.Adv.Synth.Catal.2007,349,2213;
(b) Mack,J.;Fulmer,D.;Stofel,S.;Santos,N.Green Chem.2007,9,1041;
(c) Kaupp,G.Top.Curr.Chem.2005,254,95;
(d) Balema,V.P.;Wiench,J.W.;Pruski M.;Pecharsky,V.K.J.Am.Chem.Soc.2002,124,6244;
(e) Toda,F.Acc.Chem.Res.1995,28,480.
[33]For fullerene,see:(a) For a review,see:Wang,G.-W."Fullerene Mechanochemistry",in:Encyclopedia of Nanoscience and Nanotechnology,Vol.3,(Ed.:H.S.Nalwa),American Scientific Publishers,Stevenson Ranch,2004,pp 557;
(b) Cheng,X.;Wang,G.-W.;Murata,Y.;Komatsu,K.Chin.Chem.Lett.2005,16,1327;
(c) Wang,G.-W.;Chen,Z.-X.;Murata,Y.;Komatsu,K.Tetrahedron 2005,61,4851;
(d) Peng,R.-F.;Wang,G.-W.;Shen,Y.-B.;Li,Y.-J.;Zhang,T.-H.;Liu,Y.-C.;Murata Y.;Komatsu,K.Synth.Commun.2004,34,2117;
(e) Zhang,T.-H.;Wang,G.-W.;Lu,P.;Li,Y.-J.;Peng,R.-E;Liu,Y.-C.;Murata,Y.;Komatsu,K.Org.Biomol.Chem.2004,2,1698.
[34]For non-fullerene,see:(a) Gao,J.;Wang,G.-W.J.Org.Chem.2008,73,2955;
(b) Wu,X.-L.;Xia,J.-J.;Wang,G.-W.Org.BiomoL Chem.2008,6,548;
(c) Wang,G.-W.;Wu,X.-L.Adv.Synth.Catal.2007,349,1977;
(d) Zhang,Z.;Gao,J.;Xia,J.-J.;Wang,G.-W.Org.Biomol.Chem.2005,3,1617;
(e) Zhang,Z.;Wang,G.-W.;Miao,C.-B.;Dong,Y.-W.;Shen,Y.-B.Chem.Commun.2004,1832;
(f) Zhang,Z.;Dong,Y.-W.;Wang,G.-W.;Komatsu,K.Synlett 2004,61.
[35]Babler,J.H.;Liptak,V.P.;Phan,N.J.Org.Chem.1996,61,416.
[36]Pozzo,J.-L.;Samat,A.;Guglieimetti,R.;Dubest,R.;Aubard,J.Helv.Chim.Acta.1997,80,725.
[37]Gabbutt,C.D.;Heron,B.M.;Instone,A.C.;Thomas,D.A.;Partington,S.M.;Hursthouse,M.B.;Gelbrich,T.Eur J.Org.Chem.2003,1220.
[1](a) Friedel,C.;Crafts,J.M.;Hebd.C.R.Seances Acad.Sci.1877,84,1392;
(b) Friedel,C.;Crafts,J.M.;Hebd.C.R.Seances Acad.Sci.1877,84,1450.
[2](a) Olah G.A.in Friedel-Crafts and Related Reactions,Wiley,New York,1963;
(b) Olah G.A.in Friedel-Crafts Chemistry,Wiley,New York,1973.
[3](a) Tsuchimoto,T.;Tobita,K.;Hiyama,T.;Fukuzawa,S.J.Org.Chem.1997,62,6997;
(b)Gmouh,S.;Yang,H.;Vaultier,M.Org.Lett.2003,5,2219.
[4](a) Bigi,F.;Casiraghi,G;.Casnati,G.;Sartori,G.d.Org.Chem.1985,50,5018;
(b) Erker,G.;van der Zeijden,A.A.H.Angew.Chem.,Int.Ed.1990,29,512.
[5]Johannsen,M.Chem.Commun.1999,2233.
[6](a) Saaby,S.;Fang,X.;Gathergood,N.;J(?)rgenson,K.A.Angew.Chem.,Int.Ed.2000,39,4114;
(b) Saaby,S.;Bayon,P.;Aburel,P.S.;J(?)rgenson,K.A.J.Org.Chem.2002,67,4352.
[7](a) Zhuang,W.;Hansen,T.;J(?)rgensen,K.A.Chem.Commun.2001,347;
(c) Zhou,J.;Tang,Y.Chem.Commun.2004,432;
(b) Rasappan,R.;Hager,M.;Gissibl,A.;Reiser,O.Org.Lett.2006,8,6099.
[8](a) Yang,H.;Hong,Y.T.;Kim,S.Org.Lett.2007,9,2281;
(b) Yamazaki,S.;Iwata Y.J.Org.Chem.2006,71,739;
(c) Palomo,C.;Oiarbide,M.;Kardak,B.J.;Garcia,J.M.;Linden,A.J.Am.Chem.Soc.2005,127,4154;
(d) Palomo,C.;Oiarbide,M.;Garcia,J.M.;Gonzalez, A.; Arceo, E. J. Am. Chem. Soc. 2003,125, 13942; (e) Palomo, C.; Oiarbide, M.; Haider, R.;Kelso, M.; Gomez-Bengoa, E.; Garcia J. M. J. Am. Chem. Soc. 2004,126, 9188.
[9] Singh, P. K.; Bisai, A.; Singh V. K. Tetrahedron Lett. 2007, 48,1127.
[10] Jia, Y. X.; Xie, J. H.; Duan, H. F.; Wang, L. X.; Zhou Q. L. Org. Lett. 2006, 8, 1621.
[11] (a) Zhao, J. L.; Liu, L.; Sui, Y.; Liu, Y. L.; Wang, D.; Chen Y. J. Org. Lett. 2006, 8, 6127; (b) Zhuang, W.; Gathergood, N.; Hazell, R. G.; J0rgensen, K. A. J. Org. Chem. 2001, 66, 1009.
[12] (a) Zhou, J.; Ye, M.-C; Huang, Z.-Z.; Tang, Y. J. Org. Chem. 2004, 69, 1309; (b) Zhou, J.;Tang, Y. J. Am. Chem. Soc. 2002,124, 9030.
[13] Takenaka, N.; Abell, J. P.; Yamamoto, H. J. Am. Chem. Soc. 2007,129, 742.
[14] (a) Bandini, M.; Fagioli, M.; Melchiorre, P.; Melloni, A.; Umani-Ronchi, A. Tetrahedron Lett. 2003, 44, 5843; (b) Bandini, M.; Fagioli, M.; Garavelli, M.; Melloni, A.; Trigari, V.;Umani-Ronchi, A. J. Org. Chem. 2004, 69, 7511; (c) Angeli, M.; Bandini, M.; Garavelli, M.;Piccinelli, F.; Tommasi, S.; Umani-Ronchi, A. Chem. Commun. 2006, 3291.
[15] Bandini, M.; Melloni, A.; Piccinelli, F.; Sinisi, R.; Tommasi, S.; Umani-Ronchi, A. J. Am.Chem. Soc. 2006,128, 1424.
[16] Trost, B. M.; Quancard, J. J. Am. Chem. Soc. 2006,128,6314.
[17] (a) Evans, D. A.; Frandrick, K. R.; Song, H.-J. J. Am. Chem. Soc. 2005,127, 8942; (b) Evans,D. A.; Frandrick, K. R. Org. Lett. 2006,8, 2249.
[18] (a) Jia, Y.-X.; Zhu, S.-F.; Yang, Y.; Zhou, Q.-L. J. Org. Chem. 2006, 71, 75; (b) Lu, S.-F.;Du, D.-M.; Xu, J. Org. Lett. 2006, 8, 2115.
[19] Wilson, R. M.; Thalji, R. K.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2006, 8, 1745.
[20] Blay, G.; Fernandez, I.; Pedro, J. R.; Vila, C. Org. Lett. 2007, 9,2601.
[21] Han, X.; Widenhoefer, R. A. Org. Lett. 2006, 8, 3801.
[22] (a) Paras, N. A.; Macmillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370; (b) Austin, J. F.;Macmillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172; (c) Paras, N. A.; Macmillan, D. W.C. J. Am. Chem. Soc. 2002,124, 7894.
[23] (a) Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Angew. Chem., Int. Ed. 2005, 44,6576; (b) Fleming, E. M.; McCabe, T.; Connon, S. J. Tetrahedron Lett. 2006, 47, 7037.
[24] Wang, Y.-Q.; Song, J.; Hong, R.; Li, H.; Deng, L. J. Am. Chem. Soc. 2006,128, 8156.
[25] (a) Chen, W.; Du, W.; Yue, L.; LI, R.; Wu, Y.; Ding, L.-S.; Chen, Y.-C. Org. Biomol. Chem.2007, 5, 816; (b) Bartoli, G.; Bosco, M.; Carlone, A.; Pesciaioli, F.; Sambri, L.; Melchiorre, P.Org. Lett. 2007, 9, 1403.
[26] (a) Torok, B.; Abid, M.; London, G.; Esquibel, J.; Torok, M.; Mhadgut, S. C.; Yan, P.;Parkash, G. K. S. Angew. Chem., Int. Ed. 2005, 44, 3086; (b) Li, H.; Wang, Y.-Q.; Deng, L. Org.Lett.2006,8,4063.
[27]Zhou,W.;Xu,L.-W.;Li,L.;Yang,L.;Xia,C.-G.Eur.J.Org.Chem.2006,5225.
[28]Zhuang,W.;Hagzell,R.G.;J(?)rgensen,K.A.Org.Biomol.Chem.2005,3,2566.
[29]Uraguchi,D.;Sorimachi,K.;Terada,M.J.Am.Chem.Soc.2004,126,11804.
[30](a) Jia,Y.-X.;Zhong,J.;Zhu,S.-F.;Zhang,C.-M.;Zhou,Q.-L.Angew.Chem.,Int.Ed.2007,46,5565;
(b) Kang,Q.;Zhao,Z.-A.;You,S.-L.J.Am.Chem.Soc.2007,129,1484;
(c)Terada,M.;Sorimachi,K.J.Am.Chem.Soc.2007,129,292.
[31](a) Rowland,G.B.;Rowland,E.B.;Liang,Y.;Perman,J.A.;Antilla,J.C.Org.Lett.2007,9,2609;
(b) Li,G.;Rowland,G.B.;Rowland,E.B.;Antilla,J.C.Org.Lett.2007,9,4065;
(c) Terada,M.;Yokoyama,S.;Sorimachi,K.;Uraguchi,D.Adv.Synth.Catal.2007,349,1863.
[32]Akiya ma,T.;Itoh,J.;Yokota,K.;Fuchibe,K.Angew.Chem.,Int.Ed.2004,43,1566.
[33]Uraguchi,D.;Terada,M.J.Am.Chem.Soc.2004,126,5356.
[34]Rodriguez,B.;Rantanen,T.;Bolm,C.Angew.Chem.,Int.Ed.2006,45,6924.
[35]Jia,Y.-X.;Xie,J.-H.;Duan,H.-F.;Wang,L.-X.;Zhou,Q.-L.Org.Lett.2006,8,1621.
[36]Wang,Y.-Q.;Song,J.;Hong,R.;Li,H.;Deng,L.J.Am.Chem.Soc.2006,128,8156.
[1](a) Negwer,M.Organic-chemical drugs and their synonyms:(an international survey),7th ed.;Akademie Verlag GmbH:Berlin,1994;
(b) Montgomery,J.H.Agrochemicals Desk Reference:Environmental Data;Lewis Publishers:Chelsea,MI,1993;
(c) Loutfy,R.O.;Hsiao,C.K.;Kazmaier,P.M.Photogr.Sci.Eng.1983,27,5;
(d) Schein,L.B.Electrophotography and Development Physics,2nd ed.;Springer-Verlag:Berlin,1992;
(e)Pigment Handbook;,Lewis,P.A.,Ed.;John Wiley & Sons:New York,1988;Vol.Ⅰ;
(f)D'Aprano,G.;Leclerc,M.;Zotti,G.;Schiavon,G.Chem.Mater.1995,7,33.
[2]Shi,M.;Zhao,G.-L.Tetrahedron 2004,60,2083.
[3]Palacios,F.;Alonso,C.;Rubiales,G.;Ezpeleta,J.M.Tetrahedron 2004,60,2469.
[4]Dadwai,M.;Mobin,S.M.Namboothiri,I.N.N.Org.Biomol.Chem.2006,4,252
[5]Waser,J.;Carreira,E.M.Angew.Chem.,Int.Ed.2004,43,4099-4102.
[6]Waser,J.;Carreira,E.M.J.Am.Chem.Soc.2004,126,5676-5677.
[7]Waser,J.;Gonzalez-Gomez,J.C.;Nambu,H.;Huber,P.;Carreira,E.M.Org.Lett.2005,7,4249-4252.
[8]Waser,J.;Gaspar,B.;Nambu,H.;Carreira,E.M.J.Am.Chem.Soc.2006,128,11693.
[9]Sato,M.;Gunji,Y.;Ikeno,T.;Yamada,T.Chem,Lett.2005,34,316.
[10]Aburel,P.S.;Zhuang,W.;Hazell,R.G.;Jorgensen,K.A.Org.Biomol.Chem.2005,3,2344.
[11]Poulsen,T.B.;Alemparte,C.;Jorgensen,K.A.J.Am.Chem.Soc.2005,127,11614.
[12]Bertelsen,S.;Marigo,M.;Brandes,S.;Diner,P.;Jorgensen,K.A.J.Am.Chem.Soc.2006,128,12973.
[13]Meseguer,M.;Moreno-Manas,M.;Vallribera,A.Tetrahedron Lett.2000,41,4093.
[14]Yadav,J.S.;Reddy,B.V.S.;Venugopal C.;Padmavani B.Tetrahedron Lett.2004,45,7507.
[15]Huber,D.P.;Stanek K.;Togni A.Tetrahedron:Asymmetry 2006,17,658.
[16]Comelles,J.;Pericas,A.;Moreno-Manas,M.;Vallribera,A.;Drudis-Sole,G.;Lledos,A.;Patella,T.;Roglans,A.;Garcla-Granda,S.;Roces-Fernandez,L.J.Org.Chem.2007,72,2077.
[17]Terada,M.;Nakano,M.;Ube H.J.Am.Chem.Soc.2006,128,16044.
[18]Kang,Y.K.;Kim,D.Y.Tetrahedron Lett.2006,47,4565.
[19]Duthaler,R.O.Angew.Chem.,Int.Ed.2003,42,975.
[20]Thomassigny,C.;Prim,D.;Greck,C.Tetrahedron Lett.2006,47,1117.
[21]Liu,T.-Y.;Cui,H.-L.;Zhang,Y.;Jiang,K.;Du,W.;He,Z.-Q.;Chen,Y.-C.Org.Lett.2007,9,3671.
[22]Chowdari,N.S.;Barbas,C.F.Org.Lett.2005,7,867.
[23]Saaby,S.;Bella,M.;J(?)rgensen,K.A.J.Am.Chem.Soc.2004,126,8120.
[24]Liu,X.;Li,H.;Deng,L.Org.Lett.2005,7,167.
[25]Liu,Y.;Melgar-Fernandez,R.;Juaristi,E.J.Org.Chem.2007,72,1522.
[26]Bernardi,L.;Zhuang,W.;J(?)rgensen,K.A.J.Am.Chem.Soc.2005,127,5772.
[27]Wang,M.-Z.;Xu,H.-W.;Liu,Y.;Wong,M.-K.;Che,C.-M.Adv.Synth.Catal.2006,348,2391.
[28]Korotkov,V.S.;Larionov,O.V.;Hofmeister,A.;Magull,J.;de Meijere A.J.Org.Chem.2007,72,7504.
[29]Nair,V.;Mathew,S.C.;Biju,A.T.;Suresh,E.Angew.Chem.,Int.Ed.2007,46,2070.
[30](a) Mitchell,H.;Leblanc,Y.J.Org.Chem.1994,59,682;
(b) Leblanc,Y.;Boudreault,N.J.Org.Chem.1995,60,4268.
[31]Yadav,J.S.;Reddy,B.V.S.;Kumar,G.M.;Madan,C.Synlett 2001,1781.
[32]Yadav,J.S.;Reddy,B.V.S.;Veerendhar,G.;Rao,R.S.;Nagaiah,K.Chem.Lett.2002,318.
[33]Bombek,S.;Lenarsic,R.;Kocevar,M.;Saint-Jalmes,L.;Desmurs,J.-R.;Polanc,S.Chem.Commun.2002,1494.
[34]Kinart,W.J.;Kinart,C.M.J.Organomet.Chem.2003,665,233.
[35]Bombek,S.;Pozgan,F.;Kocevar,M.;Polanc,S.J.Org.Chem.2004,69,2224.
[36]Brandes,S.;Bella,M.;Kjoersgaard,A.;J(?)rgensen,K.A.Angew.Chem.,Int.Ed.2006,45,1147.
[37]Demers,J.P.;Klaubert,D.H.Tetrahedron Lett.1987,28,4933.
[38]Katritzky,A.R.;Wu,J.;Verin,S.V.Synthesis 1995,651.
[39]Velarde-Ortiz,R.;Guijarro,A.;Rieke,R.D.Tetrahedron Lett.1998,39,9157.
[40]Stauffer,S.R.;Huang,Y.R.;Aron,Z.D.;Coletta,C.J.;Sun,J.;Katzenellenbogen,B.S.;Katzenellenbogen,J.A.Bioorg.Med.Chem.2001,9,151.
[41]Tsubrik,O.;Kisseljova,K.;M(a|¨)eorg,U.Synlett 2006,2391.
[42]Uemura,T.;Chatani,N.J.Org.Chem.2005,70,8631.
[43]Kisseljova,K.;Tsubrik,O.;Siilard,R.;M(a|¨)eorg,S.;M(a|¨)eorg,U.Org.Lett.2006,8,43.
[44]Muniz,K.;Iglesias,A.Angew.Chem.,Int.Ed.2007,46,6350.
[45]For a review,see:(a) Gribble,G.W.J.Chem.Soc.,Perkin Trans.1 2000,1045.
(b)Engeihardt,U.Coord.Chem.Rev.2002,235,53.For examples,see:
(c) Toure,B.B.;Hall,D.G.J.Org.Chem.2004,69,8429.
(d)Unciti-Broceta,A.;Pineda-de-las-Infantas,M.J.;Diaz-Mochon,J.J.;Romagnoli,R.;Baraldi,P.G.;Gallo,M.A.;Espinosa,A.J.Org.Chem.2005,70,2878.
(e) Kang,H.-M.;Lira,Y.-K.;Shin,I.-J.;Kim,H.-Y.;Cho,C.-G.Org.Lett.2006,8,2047.
(f) Rivero M.R.;Buchwald,S.L.Org.Lett.2007,9,973.
(g) Banerjee,S.;Barnea,E.;Odom,A.L.Organometallics 2008,27,1005.
[46]Dekeyser,M.A.;McDonald,P.T.;Angle,G.W.,Jr.J.Agric.FoodChem.1994,42,1358.
[47]For a review,see:(a) Ragnarsson,U.Chem.Soc.Rev.2001,30,205.For examples,see:
(b)Meyer,K.G.Synlett 2004,2355.
(c) Matunas,R.;Lai,A.J.;Lee,C.Tetrahedron 2005,61,6298.
(d) Ju,Y.;Varma,R.S.Tetrahedron Lett.2005,46,6011.
(e) Ragnarsson,U.;Grehn,L.;Koppel,J.;Loog,O.;Tsubrik,O.;Bredikhin,A.;M(a|¨)eorg,U.;Koppel,I.J.Org.Chem.2005,70,5916.
(f) Rasmussen,L.K.J.Org.Chem.2006,71,3627.
(g) Bredihhin,A.;Groth,U.M.;M(a|¨)eorg,U.Org.Lett.2007,9,1097.
(h) Bredihhin,A.;M(a|¨)eorg,U.Org.Lett.2007,9,4975.
(I) Johns,A.M.;Liu,Z.;Hartwig,J.F.Angew.Chem.,Int.Ed.2007,46,7259.
[48](a) Arterburn,J.B.;Rao,K.V.;Ramdas,R.;Dible,B.R.Org.Lett.2001,3,1351.
(b) Wolter,M.;Klapars,A.;Buchwald,S.L.Org.Lett.2001,3,3803.
(c) Ortner,B.;Waibel,R.;Gmeiner,P.Angew.Chem.,Int.Ed.2001,40,1283.
(d) Kabalka,G.W.;Guchhait,S.K.Org.Lett.2003,5,4129.
(e) Tsubrik,O.;M(a|¨)eorg,U.;Sillard,R.;Ragnarsson,U.Tetrahedron 2004,60,8363.
(f) Kim,K.-Y.;Shin,J.-T.;Lee,K.-S.;Cho,C.-G.Tetrahedron Lett.2004,45,117.
(g) Loog,O.;M(a|¨)eorg,U.Synlett 2004,2537.
(h) Cacchi,S.;Fabrizi,G.;Goggiamani,A.;Sgalla,S.Adv.Synth.Catal.2007,349,453.
(I) Liu,X.;Barry,M.;Tsou,H.-R.Tetrahedron Lett.2007,48,8409.
[49]Duthaler,R.O.Angew.Chem.,Int.Ed.2003,42,975.
[50](a) Waser,J.;Carreira,E.M.J.Am.Chem.Soc.2004,126,5676.
(b) Waser,J.;Gaspar,B.;Nambu,H.;Carreira,E.M.J.Am.Chem.Soc.2006,128,11693.
[51](a) Saaby,S.;Bella,M.;J(?)rgensen,K.A.J.Am.Chem.Soc.2004,126,8120;
(b) Hartke,K.; Brutsche,A.;Gerber,H.-D.Liebigs Ann.Chem.1992,9,927;
(c) Nelson,J.H.;Howells,P.N.;DeLullo,G.C.;Landen,G.L.;Henry,R.A.J.Org.Chem.1980,45,1246.
[52](a) Mitchell,H.;Leblanc,Y.J.Org.Chem.1994,59,682.
(b) Leblanc,Y.;Boudreault,N.J.Org.Chem.1995,60,4268.
(c)Yadav,J.S.;Reddy,B.V.S.;Kumar,G.M.;Madan,C.Synlett 2001,1781.
(d) Yadav,J.S.;Reddy,B.V.S.;Veerendhar,G.;Rao,R.S.;Nagaiah,K.Chem.Lett.2002,318.
(e) Bombek,S.;Lenarsic,R.;Kocevar,M.;Saint-Jalmes,L.;Desmurs,J.-R.;Polanc,S.Chem.Commun.2002,1494.
(f)Bombek,S.;Pozgan,F.;Kocevar,M.;Polanc,S.J.Org.Chem.2004,69,2224.
(g) Brandes,S.;Bella,M.;Kjoersgaard,A.;J(?)rgensen,K.A.Angew.Chem.,Int.Ed.2006,45,1147.
[53](a) Demers,J.P.;Klaubert,D.H.Tetrahedron Lett.1987,28,4933.
(b) Katritzky,A.R.;Wu,J.;Verin,S.V.Synthesis 1995,651.
(c) Velarde-Ortiz,R.;Guijarro,A.;Rieke,R.D.Tetrahedron Lett.1998,39,9157.
(d) Stauffer,S.R.;Huang,Y.R.;Aron,Z.D.;Coletta,C.J.;Sun,J.;Katzenellenbogen,B.S.;Katzenellenbogen,J.A.Bioorg.Med.Chem.2001,9,151.
(e) Kinart,W.J.;Kinart,C.M.J.Organomet.Chem.2003,665,233.
(f) Tsubrik,O.;Kisseljova,K.;M(a|¨)eorg,U.Synlett 2006,2391.
[54](a) Uemura,T.;Chatani,N.J.Org.Chem.2005,70,8631.
(b) Kisseljova,K.;Tsubrik,O.;Sillard,R.;M(a|¨)eorg,S.;M(a|¨)eorg,U.Org.Lett.2006,8,43.
(c) Muniz,K.;Iglesias,A.Angew.Chem.,Int.Ed.2007,46,6350.
[55](a) Collman,J.P.;Zhong,M.Org.Lett.2000,2,1233.
(b) Collman,J.P.;Zhong,M.;Zeng,L.;Costanzo,S.J.Org.Chem.2001,66,1528.
(c) Collman,J.P.;Zhong,M.;Zhang,C.;Costanzo,S.J.Org.Chem.2001,66,7892.
(d) van Berkel,S.S.;van den Hoogenband,A.;Terpstra,J.W.;Tromp,M.;van Leeuwen,P.W.N.M.;van Strijdonek,G.P.F.Tetrahedron Lett.2004,45,7659.
[56](a) Chen,G.J.-J.;McDonald,J.W.;Bravard,D.C.;Newton,W.E.Inorg.Chem.1985,24,2327;
(b) Chan,D.;Cronin,L.;Duckett,S.B.;Hupfield,P.;Perutz,R.N.New J.Chem.1998,22,511;
(c) Kumar K.V.P.P.;Kumar,N.S.;Swamy,K.C.K.New J.Chem.2006,30,717.
[57](a) Savarin,C.;Srogl,J.;Liebeskind,L.S.Org.Lett.2002,4,4309.
(b) Li,J.-H.;Li,J.-L.;Wang,D.-P.;Pi,S.-F.;Xie,Y.-X.;Zhang,M.-B.;Hu,X.-C.J.Org.Chem.2007,72,2053.
(c)Liu,S.;Yu,Y.;Liebeskind,L.S.Org.Lett.2007,9,1947.
[58]Clariana,J.;Galvez,N.;Marchi,C.;Moreno-Manas,M.;Vallribera,A.;Molins,E.Tetrahedron,1999,55,7331.
[59]Muniz,K.;Iglesias,A.Angew.Chem.,Int.Ed.2007,46,6350.
[60]Yadav,J.S.;Reddy,B.V.S.;Vennrendhar,G.;Rao,R.S.;Nagaiah,K.Chem.Lett.2002,318.
[61]Malatesta,V.;Ingold,K.U.Tetrahedron Lett.1973,14,3311.
(b)Anastas,P.T.;Warner,J.C.Green Chemistry.Frontiers in Beijing Chemical Synthesis and Processes;Oxford:Oxford Univ.Press,1998.
[2]Anastas,P.T.;Warner,J.C.Green Chemistry:Thery and Practical;New York:Oxford Univ.Press,1998.
[3]Winterton,N.Green Chem.2001,6,G73.
[4]Trost,B.M.Science 1991,254,1471.
[5]Dzyuba,S.V.;Bartsch,R.A.Angew Chem.,Int.Ed.2003,42,148.
[6](a) Doll,K.M.;Ethan,S.Z.Green Chem.2008,10,712;
(b) Walsh,P.J.;Li,H.M.;de Parrodi,C.A.Chem.Rev.2007,107,2503.
[7](a) Deng,G.J.;Fan,Q.H.;Chen,X.M.et al.Chem.Commun.2002,1570;
(b) Tang,W.J.;Yang,N.F.;Yi,B.Chem.Commun.2004,1378;
(c) Heldebrant,D.J.;Jessop,P.G.J.Am.Chem.Soc.2003,125,5600.
[8]Peters K.Mechanochemische Peaktionen.Frankfurt,1962.
[9]Heinicke G.Tribochemistry.Berlin:Akademie Verlag,1984.
[10]Garay,A.L.;Pichon,A.;James,S.L.Chem.Soc.Rev.2007,36,846.
[11]Lyakhov,N.;Grigodeva,T.;Barinova,A.;Lomayeva,S.;Yelsukov,E.;Ulyanov,A.J.Mater.Sci.2004,39,5421.
[12](a) Rodriguez,B.;Bruckmann,A.;Rantanen,T.;Bolm,C.Adv.Synth.Catal.2007,349,2213;
(b) Mack,J.;Fulmer,D.;Stofel,S.;Santos,N.Green Chem.2007,9,1041;
(c) Kaupp,G.Top.Curr.Chem.2005,254,95;
(d) Balema,V.P.;Wiench,J.W.;Pruski M.;Pecharsky,V.K.J.Am.Chem.Soc.2002,124,6244;
(e) Toda,F.Acc.Chem.Res.1995,28,480.
[13]Beyer,M.K.;Clausen-Schaumann,H.Chem.Rev.2005,105,2921.
[14]Delogu,F.;Orru,R.;Can,G.Chem.Eng.Sci.2003,58,815.
[15](a) Urakaev,F.K.;Boldyrev,V.V.Powder Technology 2000,107,93;
(b) Urakaev,F.K.;Boldyrev,V.V.Powder Technology 2000,107,197.
[16](a) Gao,J.;Wang,G.-W.J.Org.Chem.2008,73,2955;
(b) Wu,X.-L.;Xia,J.-J.;Wang,G.-W.Org.Biomol.Chem.2008,6,548;
(c) Wang,G.-W.;Wu,X.-L.Adv.Synth.Catal.2007,349, 1977;
(d) Zhang,Z.;Gao,J.;Xia,J.-J.;Wang,G.-W.Org.Biomol.Chem.2005,3,1617;
(e)Zhang,Z.;Wang,G.-W.;Miao,C.-B.;Dong,Y.-W.;Shen,Y.-B.Chem.Commun.2004,1832;
(f) Zhang,Z.;Dong,Y.-W.;Wang,G.-W.;Komatsu,K.Synlett 2004,61;
(g) Wang,G.-W.;Liu,L.Chinese Chin.Lett.2004,15,587;
(h) Zhang,Z.;Dong,Y.-W.;Wang,G.-W.Chem.Lett.2004,33,168.
[17](a) For a review,see:Wang,G.-W."Fullerene Mechanochemistry",in:Encyclopedia of Nanoscience and Nanotechnology,Vol.3,(Ed.:H.S.Nalwa),American Scientific Publishers,Stevenson Ranch,2004,pp 557;
(b) Chen,Z.-X.;Zhu,B.;Wang,G.-W.Lett.Org.Chem.2008,5,65;
(c) Cheng,X.;Wang,G.-W.;Murata,Y.;Komatsu,K.Chin.Chem.Lett.2005,16,1327;
(d) Wang,G.-W.;Chen,Z.-X.;Murata,Y.;Komatsu,K.Tetrahedron 2005,61,4851;
(e)Li,Y.-J.;Peng,R.-F.;Liu,Y.-C.;Wang,G.-W.Chin.Chem.Lett.2004,15,1265;
(f) Peng,R.-F.;Wang,G.-W.;Shen,Y.-B.;Li,Y.-J.;Zhang,T.-H.;Liu,Y.-C.;Murata Y.;Komatsu,K.Synth.Commun.2004,34,1309;
(g) Zhang,T.-H.;Wang,G.-W.;Lu,P.;Li,Y.-J.;Peng,R.-F.;Liu,Y.-C.;Murata,Y.;Komatsu,K.Org.Biomol.Chem.2004,2,1698;
(h) Zhang,T.-H.;Li,Y.-J.Peng,R.-F.;Lu,P.;Chen,Z.-X.;Wang,G.-W.Chinese J.Org.Chem.2003,23,392;
(i)Wang,G.-W.;Zhang,T.-H.;Li,Y.-J.;Lu,P.;Zhan,H.;Liu,Y.-C.;Murata,Y.;Komatsu,K.Tetrahedron Lett.2003,44,4407;
(j) Wang,G.-W.;Zhang,T.-H.;Hao,E.-H.;Jiao,L.-J.;Murata,Y.;Komatsu,K.Tetrahedron 2003,59,55.
[18]Rodriguez,B.;Rantanen T.;Bolm,C.Angew.Chem.,Int.Ed.2006,45,6924.
[19](a) Rodriguez,B.;Bruckmann,A.;Bolm,C.Chem.Eur.J.2007,13,4710;
(b) Xiong,H.;Wu,H.;Xu,G.;Yang,Y.Biochem.Eng.J.2008,138,258;
(c) Guillena,G.;del Carmen Hita,M.;Najera,C.Viozquez,S.F.J.Org.Chem.2008,73,5933;
(d) Rantanen,T.;Schiffers,I.;Bolm,C.Orgo Process Res.Dev.2007,11,592;
(e) Guillena,G.;del Carmen Hita,M.;Najera,C.Viozquez,S.F.Tetrahedron:Asymmetry 2007,18,2300.
[1]Badanyan,S.O.;Melikyan,G.G.;Mkrtchyan,D.A.Russ.Chem.Rev.1989,58,286(Usp. Khim., 1989, 55, 475).
[2] Melikyan, G. G. Synthesis 1993, 833.
[3] Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519.
[4] Snider, B. B. Chem. Rev. 1996, 96, 339.
[5] Heiba, E. I.; Dessau, R. M.; Koehl, W. J. J. Am. Chem. Soc. 1968, 90, 5905.
[6] Bush, J. B.; Finkbeiner, H. J. Am. Chem. Soc. 1968, 90, 5903.
[7] Heiba, E. I.; Dessau, R. ML, J. Org. Chem. 1974, 39, 3456.
[8] (a) Heiba, E. I.; Dessau, R. M.; Koehl, W. J. J. Am. Chem. Soc. 1968, 90, 2706; (b) Heiba, E.I.; Dessau, R. M.; Koehl, W. J. J. Am. Chem. Soc. 1969, 91, 138; (c) Heiba, E. I.; Dessau, R.M. Discuss. Faraday Soc. 1968, 46, 189; (d) Heiba, E. I.; Dessau, R. M. J. Am. Chem. Soc.1971, 93, 524; (e) Heiba, E. I.; Dessau, R. M.; Rodewald, P. G. J. Am. Chem. Soc. 1974, 96,7977; (f) Heiba, E. I.; Dessau, R. M.; Williams, A. L.; Rodewald, P. G. Org. Synth. 1983, 61,22.
[9] Bush, J. B.; Finkbeiner, H. J. Am. Chem. Soc. 1968, 90, 5903.
[10]Ploeg, R. E. V.; Korte, R. W.; Kooyman, E. C. J. Catal. 1968,10, 52.
[11](a) Nikishin, G. I.; Vinogradov, M. G.; Il'ina, G. P. Synthesis 1972, 376; (b) Nikishin, G. I.;Vinogradov, M. G.; Il'ina G. P. J. Org. Chem. 1972, 8, 1422; (c) Nikishin, G. I.; Vinogradov,M. G.; Fedorova, T. M. J. Chem. Soc, Chem. Commun. 1973, 693; (d) Vinogradov, M. G.;Fedorova, T. M.; Nikishin, G. I. J. Org. Chem. 1976, 12, 1183; (e) Vinogradov, M. G.;Verenchikov, S. P.; Nikishin, G. I. J. Org. Chem. 1976,12, 2245.
[12](a) McQuillin, F. J.; Wood, M. J. Chem. Res., Synop. 1977, 61; (b) McQuillin, F. J.; Wood, M.J. Chem. Soc, Perkin Trans. 1 1976, 1762.
[13](a) Fristad, W. E.; Peterson, J. R. J. Org. Chem. 1985, 50, 10; (b) Fristad, W. E.; Hershberger,S. S. J. Org. Chem. 1985, 50, 1026; (c) Fristad, W. E.; Peterson, J. R.; Ernst, A. B. J. Org.Chem. 1985, 50, 3143; (d) Fristad, W. E.; Brandvold, T. A.; Peterson, J.; Thompson, S. R. J.Org. Chem. 1985, 50, 3647; (e) Fristad, W. E.; Ernst, A. B. Tetrahedron Lett. 1985, 26, 3761;(f) Yann, F. Z.; Trost, M. K.; Fristad, W. E. Tetrahedron Lett. 1987. 28, 1493.
[14](a) Corey, E. J.; Kang, M.-C. J. Am. Chem. Soc. 1984,106, 5384; (b) Corey, E. J.; Gross, A.W. Tetrahedron Lett. 1985, 26, 4291.
[15](a) Corey, E. J.; Ghosh, A. K. Chem. Lett. 1987, 223; (b) Kochi, J. K.; Davis, D. D. J. Am.Chem. Soc. 1964, 86, 5264; (c) Davis, D. D.; Kochi, J. K. Nature 1964, 202, 690; (d) Kochi, J.K.; Mocadlo, P. E. J. Am. Chem. Soc. 1966, 88, 4094; (e) Kochi, J. K.; Mocadlo, P. E. J. Org.Chem. 1965, 30, 1134; (f) Kochi J. K.; Powers, S. W. J. Am. Chem. Soc. 1970, 92, 137; (g)Krusic, P. J.; Fagan, P. J.; San Filippo, J. S. J. Am. Chem. Soc. 1977, 99, 250; (h) Maillard, B.; Forrest,D.;Ingold,K.U.J.Am.Chem.Soc.1976,98,7024;
(i) Kochi,J.K.Acc.Chem.Res.1974,7,351;
(j) Inaba,S.;Ojima,I.Tetrahedron Lett.1977,18,2009.
[16]Tanyeli,C.;Ozdemirhan,D.Tetrahedron Lett.2003,44,7311.
[17]Zhu,Y.;Bahnmueller,S.;Hosmane,N.S.;Maguire,J.A.Chem.Lett.2003,32,730.
[18]Barr,G.;Parsons,A.F.;Yhomas,C.B.Org.Biomol.Chem.2003,1,373.
[19]Artis,D.R.;Cho,I.S.;Muchowski,J.M.Can.J.Chem.1992,70,1838.
[20]Rahman,M.T.;Nishino,H.Tetrahedron 2003,59,8383.
[21]Dimir,A.S.;Reis,O.;Ozgul-Karaaslan,E.J.Chem.Soc.,Perkin Trans.1 2001,3042.
[22]Demir,A.S.;Reis,O.;Emrullahoglu,M.Tetrahedron 2002,58,8055.
[23]Demir,A.S.;Reis,O.;Emrullahoglu,M.J.Org.Chem.2003,68,578.
[24]Chikaoka,S.;Toyao,A.;Ogasawara,M.;Tamura,T.;Ishibashi,H.J.Org.Chem.2003,68,312.
[25]Thomas,N.F.;Lee,J.R.;Paraidathathu,T.;Weber,J.F.F.;Awang,K.Tetrahedron Lett.2002,43,3151.
[26]Snider,B.B.;Che,Q.Heterocycles 2004,62,325.
[27]Yilmaz,M.;Uzunalioglu,N.;Pekel,A.T.Tetrahedron 2005,61,8860.
[28]Alagoz,O.;Yilmaz,M.;Pekel,A.Synth.Commum.2006,36,1005.
[29]Fu,W.-J.;Huang,X.J.Organomet.Chem.2007,692,740.
[30]Rahman,M.T.;Nishino,H.Org.Lett.2003,5,2887.
[31]Kumabe,R.;Nishino,H.Tetrahedron Lett.2004,45,703.
[32]Wang,G.-W.;Zhang,T.-H.;Cheng,X.;Wang,F.Org.Biomol.Chem.2004,2,1160.
[33]Wang,G.-W.;Fa-Bao li Org.Biomol.Chem.2005,3,794.
[34]Wang,G.-W.;Yang,H.T.;Miao,C.B.;Xu,Y.;Liu,F.Org.Biomol.Chem.2006,4,2595.
[35]Chen,Z.-X.;Wang,G.-W.J.Org.Chem.2005,70,2380.
[36]Wang,G.-W.;Li,F.-B.;Zhang T.-H.Org.Lett.2006,8,1355.
[37]Bar,G.;Parson,A.F.;Thomas,C.B.Chem.Commum.2001,1350.
[38]Liao,Y.-Y.;Wu,Y.-L.;Chuang,C.-P.Tetrahedron 2003,59,3511.
[39]Sung,K.;Wang,Y.Y.J.Org.Chem.2003,68,2771.
[40]Ryu,I.;Alper,H.J.Am.Chem.Soc.1993,115,7543.
[41]Ji,N.;Rosen,B.M.;Myers,A.G.Org.Lett.2004,6,4551.
[42]Hulcoop,D.G.;Burton,J.W.Chem.Commum.2005,4687.
[43]Demir,A.S.;Caliskan,Z.A.;Aydin,A.E.;Biter,I.Tetrahedron:Asymmetry 2006,17,786.
[44]Demir,A.S.;Reis,O.;Igdir,C.Tetrahedron 2004,60,3427.
[45]Demir,A.S.;Sesenoglu,O.Org.Lett.2002,4,2021.
[46]Fristad, W. E.; Brandvold, T. A.; Peterson, J. R.; Thompson, S. R. J. Org. Chem. 1985, 50,3647.
[47]Snider, B. B.; Duvall, J. R. Org. Lett. 2004, 6, 1265.
[48]Nguyen, V.-H.; Nishino, H.; Kajikawa, K. Tetrahedron 1998, 54, 11445.
[49]Mu, X.-J.; Zou, J.-P.; Zeng, R.-S.; Wu, J.-C. Tetrahedron Lett. 2005, 46, 4345.
[50]Tayama, O.; Nakano, A.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2004, 69, 5494.
[51]Takashi, K.; Nakano, A.; Sakaguchi, S.; Ishii, Y. Org. Lett. 2006, 8, 407.
[52]Varma, R. S.; Kumar, D. Tetrahedron Lett. 1999, 40, 21.
[53]Shing, T. K. M.; Yeung, Y.-Y.; Su, P. L. Org. Lett. 2006,8, 3149.
[54]Snider, B. B.; Zhang, Q. J. Org. Chem., 1993, 55, 3185.
[55]Snider, B. B.; McCarthy, B. A. J. Org. Chem., 1993, 58,6217.
[56]Zhang, Q.; Mohan, R. M.; Cook, L.; Kazanis, S.; Peisach, D.; Foxman, B. M.; Snider, B. B. J.Org. Chem., 1993,55,7640.
[57]Vo, N. H.; Snider, B. B. J. Org. Chem., 1994, 59, 5419.
[58]Snider, B. B.; O'Neil, S. Tetrahedron, 1995, 51, 12983.
[59](a)Garzino, F.; Meou, A.; Brun, P. Tetrahedron lett. 2000, 41, 9803; (b) Garzino, F.; Meou, A.;Brun, P. Eur. J. Org. Chem. 2003, 1410; (c) Martinet, S.; Meou, A.; Brun, P.; Magn. Reson.Chem. 2007, 45, 182; (d) Garzino, F.; Meou, A.; Brun, P. Helv. Chim. Ada 2002, 55, 1989; (e) Garzino, F.; Meou, A.; Brun, P. Tetrahedron Lett. 2002, 43, 5049.
[60](a) Meou, A.; Lamarque, L.; Brun, P. Tetrahedron lett. 2002, 43, 5301. (b) Lamarque, L.;Meou, A.; Brun, P. Tetrahedron lett. 1998, 39, 8283.
[61]Shanmugam, P.; Kumar, K. H.; Perumal, P. T. J. Heterocycl. Chem. 2007, 44, 827.
[62]Zhang, Z.; Wang, G.-W.; Miao, C.-B.; Dong, Y.-W.; Shen, Y.-B. Chem. Commun. 2004, 1832.
[63](a) Yang, Z.; Fan, M.; Mu, R.; Liu, W.; Liang, Y. Tetrahedron 2005, 61, 9140. (b) Cao, W.;Chen, G.; Chen, J.; Chen, R. Synth. Commun. 2005, 35, 527; (c) Pohmakotr, M.; Issaree, A.;Sampaongoen, L.; Tuchinda, P.; Reutrakul, V. Tetrahedron Lett. 2003, 44, 7937.
[64](a) Zhang, W.; Huo, C. D.; Liu, Z. G.; Liu, Z. L. Chin. Chem. Lett. 2004,15, 389; (b) Roy, S.C.; Mandal, P. K. Tetrahedron 1996, 52,2193.
[65] (a) Cossy, J.; Bouzide, A.; Leblanc, C. J. Org. Chem. 2000, 65, 7257. (b) Wang, G.-W.; Li,F.-B. Org. Biomol. Chem. 2005, 3, 794.
[66](a) Milios, C. J.; Stamatatos, T. C.; Kyritsis, P.; Terzis, A.; Raptopoulou, C. P.; Vicente, R.;Escuer, A.; Perlepes, S. P. Eur. J. Inorg. Chem. 2004, 2885. (b) Friestad, G. K. Eur. J. Org.Chem. 2005, 3157. (c) Sugiura, M.; Kobayashi, S. Angew. Chem., Int. Ed. 2005, 44, 5176.
[1]For a review,see:Cozzi,P.G.;Hilgraf,R.;Zimmermann,N.Eur.J.Org.Chem.2004,4095.
[2]Brandsma,L.Preparative Acetylenic Chemistry;Elsevier:Amsterdam,1988;p79.
[3]Eaton,P.E.;Srikrishna,A.;Uggeri,F.J.Org.Chem.1984,49,1728.
[4]Viehe,H.G.;Reinstein,M.Chem.Ber.1962,95,2557.
[5]Fisch,A.;Coisne,J.M.;Figeys,H.P.Synthesis 1982,211.
[6](a) Evans,J.C.;Goralski,C.T.;Hasha,D.L.J.Org.Chem.1992,57,2941;
(b) Brown,H.C.;Molander,G.A.;Singh,S.M.;Racherla,U.S.J.Org.Chem.1985,50,1577.
[7]Ahn,J.H.;Joung,M.J.;Yoon,N.M.J.Org.Chem.1995,60,6173.
[8]Imamoto,T.;Sugiura,Y.;Takiyama,N.Tetrahedron Lett.1984,25,4233.
[9]Hirao,T.;Misu,D.;Agawa,T.Tetrahedron Lett.1986,27,933.
[10]Yamaguchi,M.;Hayashi,A.;Minami,T.J.Org.Chem.1991,56,4091.
[11]Yamaguchi,M.;Hayashi,A.;Hirama,M.Chem.Lett.1992,2479.
[12]Han,Y.;Huang,Y.-Z.Tetrahedron Lett.1995,36,7277.
[13]Jiang,B.;Si,Y.-G.Tetrahedron Lett.2002,43,8323.
[14]Sakai,N.;Hirasawa,M.;Konakahara,T.Tetrahedron Lett.2003,44,4171.
[15]Takita,R.;Fukuta,Y.;Tsuji,R.;Ohshima,T.;Shibasaki,M.Org.Lett.2005,7,1363.
[16]Fassler,R.;Tomooka,C.S.;Frantz,D.E.;Carreira,E.M.PNAS 2004,101,5843.
[17]Babler,J.H.;Liptak,V.P.;Phan,N.J.Org.Chem.1996,61,416.
[18]Tzalis,D.;Knochel,P.Angew.Chem.,Int.Ed.1999,38,1463.
[19]Ishikawa,T.;Mizuta,T.;Hagiwara,K.;Aikawa,T.;Kudo,T.;Saito,S.J.Org.Chem.2003,68,3702.
[20]Imahori,T.;Hori,C.;Kondo,Y.Adv.Synth.Catal.2004,346,1090.
[21](a) Kuo,D.L.U.S.Patent 5 919 992,1999;
(b) Patents are cited by Tedeschi,R.J.;Casey,A.W.;Clark,G.S.,Jr.;Huckel,R.W.;Kindley,L.M.;Russell,J.P.J.Org.Chem.1963,28,1740.
[22](a) Moorthy,J.N.;Venkatakrishnan,P.;Samanta,S.;Kumar,D.K.Org.Lett.2007,9,919;
(b)Frigoli,M.;Mehl,G.H.Angew.Chem.,Int.Ed.2005,44,5048;
(c) Queiroz,M.-J.R.P.;Abreu,A.S.;Ferreira,P.M.T.;Oliveira,M.M.;Dubest,R.;Aubard,J.;Samat,A.Org.Lett.2005,7,4811;
(d) Kaneko,T.;Akutsu,H.;Yamada,J.-I.;Nakatsuji,S.Org.Lett.2003,5,2127;
(e) Samat,A.;Lokshin,V.;Chamontin,K.;Levi,D.;Pepe,G.;Guglielmetti,R.Tetrahedron 2001,57,7349;
(f) Gabbutt,C.D.;Hepworth,J.D.;Heron,B.M.;Partington,S.M.Dyes and Pigments 2000,47,73;
(g) Stauffer,M.T.;Knowles,D.B.;Brennan,C.;Funderburk,L.;Lin,F.-T.;Weber,S.G.Chem.Commun.1997,287.
[23]Bigi,F.;Carloni,S.;Maggi,R.;Muchetti,C.;Sartori,G.J.Org.Chem.1997,62,7024.
[24]Nishibayashi,Y.;Inada,Y.;Hidai,M.;Uemura,S.J.Am.Chem.Soc.2002,124,7900.
[25]Gabbutt,C.D.;Heron,B.M.;Instone,A.C.;Thomas,D.A.;Partington,S.M.;Hursthouse,M.B.;Gelbrich,T.Eur J.Org.Chem.2003,1220.
[26]Zhao,W.;Carreira,E.M.Org.Lett.2003,5,4153.
[27]Gabbutt,C.D.;Heron,B.M.;Instone,A.C.;Horton,P.N.;Hursthouse,M.B.Tetrahedron 2005,61,463.
[28]Baldoumi,V.;Gautam,D.R.;Litinas,K.E.;Nicolaides,D.N.Tetrahedron 2006,62,8016.
[29]Zhao,W.;Carreira,E.M.Org.Lett.2006,8,99.
[30]Worlikar,S.A.;Kesharwani,T.;Yao,T.;Larock,R.C.J.Org.Chem.2007,72,1347.
[31]Tanaka,K.;Aoki,H.;Hosomi,H.;Ohba,S.Org.Lett.2000,2,2133.
[32](a) Rodriguez,B.;Bruckmann,A.;Rantanen,T.;Bolm,C.Adv.Synth.Catal.2007,349,2213;
(b) Mack,J.;Fulmer,D.;Stofel,S.;Santos,N.Green Chem.2007,9,1041;
(c) Kaupp,G.Top.Curr.Chem.2005,254,95;
(d) Balema,V.P.;Wiench,J.W.;Pruski M.;Pecharsky,V.K.J.Am.Chem.Soc.2002,124,6244;
(e) Toda,F.Acc.Chem.Res.1995,28,480.
[33]For fullerene,see:(a) For a review,see:Wang,G.-W."Fullerene Mechanochemistry",in:Encyclopedia of Nanoscience and Nanotechnology,Vol.3,(Ed.:H.S.Nalwa),American Scientific Publishers,Stevenson Ranch,2004,pp 557;
(b) Cheng,X.;Wang,G.-W.;Murata,Y.;Komatsu,K.Chin.Chem.Lett.2005,16,1327;
(c) Wang,G.-W.;Chen,Z.-X.;Murata,Y.;Komatsu,K.Tetrahedron 2005,61,4851;
(d) Peng,R.-F.;Wang,G.-W.;Shen,Y.-B.;Li,Y.-J.;Zhang,T.-H.;Liu,Y.-C.;Murata Y.;Komatsu,K.Synth.Commun.2004,34,2117;
(e) Zhang,T.-H.;Wang,G.-W.;Lu,P.;Li,Y.-J.;Peng,R.-E;Liu,Y.-C.;Murata,Y.;Komatsu,K.Org.Biomol.Chem.2004,2,1698.
[34]For non-fullerene,see:(a) Gao,J.;Wang,G.-W.J.Org.Chem.2008,73,2955;
(b) Wu,X.-L.;Xia,J.-J.;Wang,G.-W.Org.BiomoL Chem.2008,6,548;
(c) Wang,G.-W.;Wu,X.-L.Adv.Synth.Catal.2007,349,1977;
(d) Zhang,Z.;Gao,J.;Xia,J.-J.;Wang,G.-W.Org.Biomol.Chem.2005,3,1617;
(e) Zhang,Z.;Wang,G.-W.;Miao,C.-B.;Dong,Y.-W.;Shen,Y.-B.Chem.Commun.2004,1832;
(f) Zhang,Z.;Dong,Y.-W.;Wang,G.-W.;Komatsu,K.Synlett 2004,61.
[35]Babler,J.H.;Liptak,V.P.;Phan,N.J.Org.Chem.1996,61,416.
[36]Pozzo,J.-L.;Samat,A.;Guglieimetti,R.;Dubest,R.;Aubard,J.Helv.Chim.Acta.1997,80,725.
[37]Gabbutt,C.D.;Heron,B.M.;Instone,A.C.;Thomas,D.A.;Partington,S.M.;Hursthouse,M.B.;Gelbrich,T.Eur J.Org.Chem.2003,1220.
[1](a) Friedel,C.;Crafts,J.M.;Hebd.C.R.Seances Acad.Sci.1877,84,1392;
(b) Friedel,C.;Crafts,J.M.;Hebd.C.R.Seances Acad.Sci.1877,84,1450.
[2](a) Olah G.A.in Friedel-Crafts and Related Reactions,Wiley,New York,1963;
(b) Olah G.A.in Friedel-Crafts Chemistry,Wiley,New York,1973.
[3](a) Tsuchimoto,T.;Tobita,K.;Hiyama,T.;Fukuzawa,S.J.Org.Chem.1997,62,6997;
(b)Gmouh,S.;Yang,H.;Vaultier,M.Org.Lett.2003,5,2219.
[4](a) Bigi,F.;Casiraghi,G;.Casnati,G.;Sartori,G.d.Org.Chem.1985,50,5018;
(b) Erker,G.;van der Zeijden,A.A.H.Angew.Chem.,Int.Ed.1990,29,512.
[5]Johannsen,M.Chem.Commun.1999,2233.
[6](a) Saaby,S.;Fang,X.;Gathergood,N.;J(?)rgenson,K.A.Angew.Chem.,Int.Ed.2000,39,4114;
(b) Saaby,S.;Bayon,P.;Aburel,P.S.;J(?)rgenson,K.A.J.Org.Chem.2002,67,4352.
[7](a) Zhuang,W.;Hansen,T.;J(?)rgensen,K.A.Chem.Commun.2001,347;
(c) Zhou,J.;Tang,Y.Chem.Commun.2004,432;
(b) Rasappan,R.;Hager,M.;Gissibl,A.;Reiser,O.Org.Lett.2006,8,6099.
[8](a) Yang,H.;Hong,Y.T.;Kim,S.Org.Lett.2007,9,2281;
(b) Yamazaki,S.;Iwata Y.J.Org.Chem.2006,71,739;
(c) Palomo,C.;Oiarbide,M.;Kardak,B.J.;Garcia,J.M.;Linden,A.J.Am.Chem.Soc.2005,127,4154;
(d) Palomo,C.;Oiarbide,M.;Garcia,J.M.;Gonzalez, A.; Arceo, E. J. Am. Chem. Soc. 2003,125, 13942; (e) Palomo, C.; Oiarbide, M.; Haider, R.;Kelso, M.; Gomez-Bengoa, E.; Garcia J. M. J. Am. Chem. Soc. 2004,126, 9188.
[9] Singh, P. K.; Bisai, A.; Singh V. K. Tetrahedron Lett. 2007, 48,1127.
[10] Jia, Y. X.; Xie, J. H.; Duan, H. F.; Wang, L. X.; Zhou Q. L. Org. Lett. 2006, 8, 1621.
[11] (a) Zhao, J. L.; Liu, L.; Sui, Y.; Liu, Y. L.; Wang, D.; Chen Y. J. Org. Lett. 2006, 8, 6127; (b) Zhuang, W.; Gathergood, N.; Hazell, R. G.; J0rgensen, K. A. J. Org. Chem. 2001, 66, 1009.
[12] (a) Zhou, J.; Ye, M.-C; Huang, Z.-Z.; Tang, Y. J. Org. Chem. 2004, 69, 1309; (b) Zhou, J.;Tang, Y. J. Am. Chem. Soc. 2002,124, 9030.
[13] Takenaka, N.; Abell, J. P.; Yamamoto, H. J. Am. Chem. Soc. 2007,129, 742.
[14] (a) Bandini, M.; Fagioli, M.; Melchiorre, P.; Melloni, A.; Umani-Ronchi, A. Tetrahedron Lett. 2003, 44, 5843; (b) Bandini, M.; Fagioli, M.; Garavelli, M.; Melloni, A.; Trigari, V.;Umani-Ronchi, A. J. Org. Chem. 2004, 69, 7511; (c) Angeli, M.; Bandini, M.; Garavelli, M.;Piccinelli, F.; Tommasi, S.; Umani-Ronchi, A. Chem. Commun. 2006, 3291.
[15] Bandini, M.; Melloni, A.; Piccinelli, F.; Sinisi, R.; Tommasi, S.; Umani-Ronchi, A. J. Am.Chem. Soc. 2006,128, 1424.
[16] Trost, B. M.; Quancard, J. J. Am. Chem. Soc. 2006,128,6314.
[17] (a) Evans, D. A.; Frandrick, K. R.; Song, H.-J. J. Am. Chem. Soc. 2005,127, 8942; (b) Evans,D. A.; Frandrick, K. R. Org. Lett. 2006,8, 2249.
[18] (a) Jia, Y.-X.; Zhu, S.-F.; Yang, Y.; Zhou, Q.-L. J. Org. Chem. 2006, 71, 75; (b) Lu, S.-F.;Du, D.-M.; Xu, J. Org. Lett. 2006, 8, 2115.
[19] Wilson, R. M.; Thalji, R. K.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2006, 8, 1745.
[20] Blay, G.; Fernandez, I.; Pedro, J. R.; Vila, C. Org. Lett. 2007, 9,2601.
[21] Han, X.; Widenhoefer, R. A. Org. Lett. 2006, 8, 3801.
[22] (a) Paras, N. A.; Macmillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370; (b) Austin, J. F.;Macmillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172; (c) Paras, N. A.; Macmillan, D. W.C. J. Am. Chem. Soc. 2002,124, 7894.
[23] (a) Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Angew. Chem., Int. Ed. 2005, 44,6576; (b) Fleming, E. M.; McCabe, T.; Connon, S. J. Tetrahedron Lett. 2006, 47, 7037.
[24] Wang, Y.-Q.; Song, J.; Hong, R.; Li, H.; Deng, L. J. Am. Chem. Soc. 2006,128, 8156.
[25] (a) Chen, W.; Du, W.; Yue, L.; LI, R.; Wu, Y.; Ding, L.-S.; Chen, Y.-C. Org. Biomol. Chem.2007, 5, 816; (b) Bartoli, G.; Bosco, M.; Carlone, A.; Pesciaioli, F.; Sambri, L.; Melchiorre, P.Org. Lett. 2007, 9, 1403.
[26] (a) Torok, B.; Abid, M.; London, G.; Esquibel, J.; Torok, M.; Mhadgut, S. C.; Yan, P.;Parkash, G. K. S. Angew. Chem., Int. Ed. 2005, 44, 3086; (b) Li, H.; Wang, Y.-Q.; Deng, L. Org.Lett.2006,8,4063.
[27]Zhou,W.;Xu,L.-W.;Li,L.;Yang,L.;Xia,C.-G.Eur.J.Org.Chem.2006,5225.
[28]Zhuang,W.;Hagzell,R.G.;J(?)rgensen,K.A.Org.Biomol.Chem.2005,3,2566.
[29]Uraguchi,D.;Sorimachi,K.;Terada,M.J.Am.Chem.Soc.2004,126,11804.
[30](a) Jia,Y.-X.;Zhong,J.;Zhu,S.-F.;Zhang,C.-M.;Zhou,Q.-L.Angew.Chem.,Int.Ed.2007,46,5565;
(b) Kang,Q.;Zhao,Z.-A.;You,S.-L.J.Am.Chem.Soc.2007,129,1484;
(c)Terada,M.;Sorimachi,K.J.Am.Chem.Soc.2007,129,292.
[31](a) Rowland,G.B.;Rowland,E.B.;Liang,Y.;Perman,J.A.;Antilla,J.C.Org.Lett.2007,9,2609;
(b) Li,G.;Rowland,G.B.;Rowland,E.B.;Antilla,J.C.Org.Lett.2007,9,4065;
(c) Terada,M.;Yokoyama,S.;Sorimachi,K.;Uraguchi,D.Adv.Synth.Catal.2007,349,1863.
[32]Akiya ma,T.;Itoh,J.;Yokota,K.;Fuchibe,K.Angew.Chem.,Int.Ed.2004,43,1566.
[33]Uraguchi,D.;Terada,M.J.Am.Chem.Soc.2004,126,5356.
[34]Rodriguez,B.;Rantanen,T.;Bolm,C.Angew.Chem.,Int.Ed.2006,45,6924.
[35]Jia,Y.-X.;Xie,J.-H.;Duan,H.-F.;Wang,L.-X.;Zhou,Q.-L.Org.Lett.2006,8,1621.
[36]Wang,Y.-Q.;Song,J.;Hong,R.;Li,H.;Deng,L.J.Am.Chem.Soc.2006,128,8156.
[1](a) Negwer,M.Organic-chemical drugs and their synonyms:(an international survey),7th ed.;Akademie Verlag GmbH:Berlin,1994;
(b) Montgomery,J.H.Agrochemicals Desk Reference:Environmental Data;Lewis Publishers:Chelsea,MI,1993;
(c) Loutfy,R.O.;Hsiao,C.K.;Kazmaier,P.M.Photogr.Sci.Eng.1983,27,5;
(d) Schein,L.B.Electrophotography and Development Physics,2nd ed.;Springer-Verlag:Berlin,1992;
(e)Pigment Handbook;,Lewis,P.A.,Ed.;John Wiley & Sons:New York,1988;Vol.Ⅰ;
(f)D'Aprano,G.;Leclerc,M.;Zotti,G.;Schiavon,G.Chem.Mater.1995,7,33.
[2]Shi,M.;Zhao,G.-L.Tetrahedron 2004,60,2083.
[3]Palacios,F.;Alonso,C.;Rubiales,G.;Ezpeleta,J.M.Tetrahedron 2004,60,2469.
[4]Dadwai,M.;Mobin,S.M.Namboothiri,I.N.N.Org.Biomol.Chem.2006,4,252
[5]Waser,J.;Carreira,E.M.Angew.Chem.,Int.Ed.2004,43,4099-4102.
[6]Waser,J.;Carreira,E.M.J.Am.Chem.Soc.2004,126,5676-5677.
[7]Waser,J.;Gonzalez-Gomez,J.C.;Nambu,H.;Huber,P.;Carreira,E.M.Org.Lett.2005,7,4249-4252.
[8]Waser,J.;Gaspar,B.;Nambu,H.;Carreira,E.M.J.Am.Chem.Soc.2006,128,11693.
[9]Sato,M.;Gunji,Y.;Ikeno,T.;Yamada,T.Chem,Lett.2005,34,316.
[10]Aburel,P.S.;Zhuang,W.;Hazell,R.G.;Jorgensen,K.A.Org.Biomol.Chem.2005,3,2344.
[11]Poulsen,T.B.;Alemparte,C.;Jorgensen,K.A.J.Am.Chem.Soc.2005,127,11614.
[12]Bertelsen,S.;Marigo,M.;Brandes,S.;Diner,P.;Jorgensen,K.A.J.Am.Chem.Soc.2006,128,12973.
[13]Meseguer,M.;Moreno-Manas,M.;Vallribera,A.Tetrahedron Lett.2000,41,4093.
[14]Yadav,J.S.;Reddy,B.V.S.;Venugopal C.;Padmavani B.Tetrahedron Lett.2004,45,7507.
[15]Huber,D.P.;Stanek K.;Togni A.Tetrahedron:Asymmetry 2006,17,658.
[16]Comelles,J.;Pericas,A.;Moreno-Manas,M.;Vallribera,A.;Drudis-Sole,G.;Lledos,A.;Patella,T.;Roglans,A.;Garcla-Granda,S.;Roces-Fernandez,L.J.Org.Chem.2007,72,2077.
[17]Terada,M.;Nakano,M.;Ube H.J.Am.Chem.Soc.2006,128,16044.
[18]Kang,Y.K.;Kim,D.Y.Tetrahedron Lett.2006,47,4565.
[19]Duthaler,R.O.Angew.Chem.,Int.Ed.2003,42,975.
[20]Thomassigny,C.;Prim,D.;Greck,C.Tetrahedron Lett.2006,47,1117.
[21]Liu,T.-Y.;Cui,H.-L.;Zhang,Y.;Jiang,K.;Du,W.;He,Z.-Q.;Chen,Y.-C.Org.Lett.2007,9,3671.
[22]Chowdari,N.S.;Barbas,C.F.Org.Lett.2005,7,867.
[23]Saaby,S.;Bella,M.;J(?)rgensen,K.A.J.Am.Chem.Soc.2004,126,8120.
[24]Liu,X.;Li,H.;Deng,L.Org.Lett.2005,7,167.
[25]Liu,Y.;Melgar-Fernandez,R.;Juaristi,E.J.Org.Chem.2007,72,1522.
[26]Bernardi,L.;Zhuang,W.;J(?)rgensen,K.A.J.Am.Chem.Soc.2005,127,5772.
[27]Wang,M.-Z.;Xu,H.-W.;Liu,Y.;Wong,M.-K.;Che,C.-M.Adv.Synth.Catal.2006,348,2391.
[28]Korotkov,V.S.;Larionov,O.V.;Hofmeister,A.;Magull,J.;de Meijere A.J.Org.Chem.2007,72,7504.
[29]Nair,V.;Mathew,S.C.;Biju,A.T.;Suresh,E.Angew.Chem.,Int.Ed.2007,46,2070.
[30](a) Mitchell,H.;Leblanc,Y.J.Org.Chem.1994,59,682;
(b) Leblanc,Y.;Boudreault,N.J.Org.Chem.1995,60,4268.
[31]Yadav,J.S.;Reddy,B.V.S.;Kumar,G.M.;Madan,C.Synlett 2001,1781.
[32]Yadav,J.S.;Reddy,B.V.S.;Veerendhar,G.;Rao,R.S.;Nagaiah,K.Chem.Lett.2002,318.
[33]Bombek,S.;Lenarsic,R.;Kocevar,M.;Saint-Jalmes,L.;Desmurs,J.-R.;Polanc,S.Chem.Commun.2002,1494.
[34]Kinart,W.J.;Kinart,C.M.J.Organomet.Chem.2003,665,233.
[35]Bombek,S.;Pozgan,F.;Kocevar,M.;Polanc,S.J.Org.Chem.2004,69,2224.
[36]Brandes,S.;Bella,M.;Kjoersgaard,A.;J(?)rgensen,K.A.Angew.Chem.,Int.Ed.2006,45,1147.
[37]Demers,J.P.;Klaubert,D.H.Tetrahedron Lett.1987,28,4933.
[38]Katritzky,A.R.;Wu,J.;Verin,S.V.Synthesis 1995,651.
[39]Velarde-Ortiz,R.;Guijarro,A.;Rieke,R.D.Tetrahedron Lett.1998,39,9157.
[40]Stauffer,S.R.;Huang,Y.R.;Aron,Z.D.;Coletta,C.J.;Sun,J.;Katzenellenbogen,B.S.;Katzenellenbogen,J.A.Bioorg.Med.Chem.2001,9,151.
[41]Tsubrik,O.;Kisseljova,K.;M(a|¨)eorg,U.Synlett 2006,2391.
[42]Uemura,T.;Chatani,N.J.Org.Chem.2005,70,8631.
[43]Kisseljova,K.;Tsubrik,O.;Siilard,R.;M(a|¨)eorg,S.;M(a|¨)eorg,U.Org.Lett.2006,8,43.
[44]Muniz,K.;Iglesias,A.Angew.Chem.,Int.Ed.2007,46,6350.
[45]For a review,see:(a) Gribble,G.W.J.Chem.Soc.,Perkin Trans.1 2000,1045.
(b)Engeihardt,U.Coord.Chem.Rev.2002,235,53.For examples,see:
(c) Toure,B.B.;Hall,D.G.J.Org.Chem.2004,69,8429.
(d)Unciti-Broceta,A.;Pineda-de-las-Infantas,M.J.;Diaz-Mochon,J.J.;Romagnoli,R.;Baraldi,P.G.;Gallo,M.A.;Espinosa,A.J.Org.Chem.2005,70,2878.
(e) Kang,H.-M.;Lira,Y.-K.;Shin,I.-J.;Kim,H.-Y.;Cho,C.-G.Org.Lett.2006,8,2047.
(f) Rivero M.R.;Buchwald,S.L.Org.Lett.2007,9,973.
(g) Banerjee,S.;Barnea,E.;Odom,A.L.Organometallics 2008,27,1005.
[46]Dekeyser,M.A.;McDonald,P.T.;Angle,G.W.,Jr.J.Agric.FoodChem.1994,42,1358.
[47]For a review,see:(a) Ragnarsson,U.Chem.Soc.Rev.2001,30,205.For examples,see:
(b)Meyer,K.G.Synlett 2004,2355.
(c) Matunas,R.;Lai,A.J.;Lee,C.Tetrahedron 2005,61,6298.
(d) Ju,Y.;Varma,R.S.Tetrahedron Lett.2005,46,6011.
(e) Ragnarsson,U.;Grehn,L.;Koppel,J.;Loog,O.;Tsubrik,O.;Bredikhin,A.;M(a|¨)eorg,U.;Koppel,I.J.Org.Chem.2005,70,5916.
(f) Rasmussen,L.K.J.Org.Chem.2006,71,3627.
(g) Bredihhin,A.;Groth,U.M.;M(a|¨)eorg,U.Org.Lett.2007,9,1097.
(h) Bredihhin,A.;M(a|¨)eorg,U.Org.Lett.2007,9,4975.
(I) Johns,A.M.;Liu,Z.;Hartwig,J.F.Angew.Chem.,Int.Ed.2007,46,7259.
[48](a) Arterburn,J.B.;Rao,K.V.;Ramdas,R.;Dible,B.R.Org.Lett.2001,3,1351.
(b) Wolter,M.;Klapars,A.;Buchwald,S.L.Org.Lett.2001,3,3803.
(c) Ortner,B.;Waibel,R.;Gmeiner,P.Angew.Chem.,Int.Ed.2001,40,1283.
(d) Kabalka,G.W.;Guchhait,S.K.Org.Lett.2003,5,4129.
(e) Tsubrik,O.;M(a|¨)eorg,U.;Sillard,R.;Ragnarsson,U.Tetrahedron 2004,60,8363.
(f) Kim,K.-Y.;Shin,J.-T.;Lee,K.-S.;Cho,C.-G.Tetrahedron Lett.2004,45,117.
(g) Loog,O.;M(a|¨)eorg,U.Synlett 2004,2537.
(h) Cacchi,S.;Fabrizi,G.;Goggiamani,A.;Sgalla,S.Adv.Synth.Catal.2007,349,453.
(I) Liu,X.;Barry,M.;Tsou,H.-R.Tetrahedron Lett.2007,48,8409.
[49]Duthaler,R.O.Angew.Chem.,Int.Ed.2003,42,975.
[50](a) Waser,J.;Carreira,E.M.J.Am.Chem.Soc.2004,126,5676.
(b) Waser,J.;Gaspar,B.;Nambu,H.;Carreira,E.M.J.Am.Chem.Soc.2006,128,11693.
[51](a) Saaby,S.;Bella,M.;J(?)rgensen,K.A.J.Am.Chem.Soc.2004,126,8120;
(b) Hartke,K.; Brutsche,A.;Gerber,H.-D.Liebigs Ann.Chem.1992,9,927;
(c) Nelson,J.H.;Howells,P.N.;DeLullo,G.C.;Landen,G.L.;Henry,R.A.J.Org.Chem.1980,45,1246.
[52](a) Mitchell,H.;Leblanc,Y.J.Org.Chem.1994,59,682.
(b) Leblanc,Y.;Boudreault,N.J.Org.Chem.1995,60,4268.
(c)Yadav,J.S.;Reddy,B.V.S.;Kumar,G.M.;Madan,C.Synlett 2001,1781.
(d) Yadav,J.S.;Reddy,B.V.S.;Veerendhar,G.;Rao,R.S.;Nagaiah,K.Chem.Lett.2002,318.
(e) Bombek,S.;Lenarsic,R.;Kocevar,M.;Saint-Jalmes,L.;Desmurs,J.-R.;Polanc,S.Chem.Commun.2002,1494.
(f)Bombek,S.;Pozgan,F.;Kocevar,M.;Polanc,S.J.Org.Chem.2004,69,2224.
(g) Brandes,S.;Bella,M.;Kjoersgaard,A.;J(?)rgensen,K.A.Angew.Chem.,Int.Ed.2006,45,1147.
[53](a) Demers,J.P.;Klaubert,D.H.Tetrahedron Lett.1987,28,4933.
(b) Katritzky,A.R.;Wu,J.;Verin,S.V.Synthesis 1995,651.
(c) Velarde-Ortiz,R.;Guijarro,A.;Rieke,R.D.Tetrahedron Lett.1998,39,9157.
(d) Stauffer,S.R.;Huang,Y.R.;Aron,Z.D.;Coletta,C.J.;Sun,J.;Katzenellenbogen,B.S.;Katzenellenbogen,J.A.Bioorg.Med.Chem.2001,9,151.
(e) Kinart,W.J.;Kinart,C.M.J.Organomet.Chem.2003,665,233.
(f) Tsubrik,O.;Kisseljova,K.;M(a|¨)eorg,U.Synlett 2006,2391.
[54](a) Uemura,T.;Chatani,N.J.Org.Chem.2005,70,8631.
(b) Kisseljova,K.;Tsubrik,O.;Sillard,R.;M(a|¨)eorg,S.;M(a|¨)eorg,U.Org.Lett.2006,8,43.
(c) Muniz,K.;Iglesias,A.Angew.Chem.,Int.Ed.2007,46,6350.
[55](a) Collman,J.P.;Zhong,M.Org.Lett.2000,2,1233.
(b) Collman,J.P.;Zhong,M.;Zeng,L.;Costanzo,S.J.Org.Chem.2001,66,1528.
(c) Collman,J.P.;Zhong,M.;Zhang,C.;Costanzo,S.J.Org.Chem.2001,66,7892.
(d) van Berkel,S.S.;van den Hoogenband,A.;Terpstra,J.W.;Tromp,M.;van Leeuwen,P.W.N.M.;van Strijdonek,G.P.F.Tetrahedron Lett.2004,45,7659.
[56](a) Chen,G.J.-J.;McDonald,J.W.;Bravard,D.C.;Newton,W.E.Inorg.Chem.1985,24,2327;
(b) Chan,D.;Cronin,L.;Duckett,S.B.;Hupfield,P.;Perutz,R.N.New J.Chem.1998,22,511;
(c) Kumar K.V.P.P.;Kumar,N.S.;Swamy,K.C.K.New J.Chem.2006,30,717.
[57](a) Savarin,C.;Srogl,J.;Liebeskind,L.S.Org.Lett.2002,4,4309.
(b) Li,J.-H.;Li,J.-L.;Wang,D.-P.;Pi,S.-F.;Xie,Y.-X.;Zhang,M.-B.;Hu,X.-C.J.Org.Chem.2007,72,2053.
(c)Liu,S.;Yu,Y.;Liebeskind,L.S.Org.Lett.2007,9,1947.
[58]Clariana,J.;Galvez,N.;Marchi,C.;Moreno-Manas,M.;Vallribera,A.;Molins,E.Tetrahedron,1999,55,7331.
[59]Muniz,K.;Iglesias,A.Angew.Chem.,Int.Ed.2007,46,6350.
[60]Yadav,J.S.;Reddy,B.V.S.;Vennrendhar,G.;Rao,R.S.;Nagaiah,K.Chem.Lett.2002,318.
[61]Malatesta,V.;Ingold,K.U.Tetrahedron Lett.1973,14,3311.