铜催化肟的偶联反应研究
摘要
作为一类重要的含氮化合物,肟及其衍生物合成胺、药物中间体以及其他具有生物活性的化合物等方面具有很重要的用途。同时肟类化合物也被广泛应用于醛酮的保护与脱保护、贝克曼重排合成酰胺、醛肟脱水合成腈等方面。近年来随着对过渡金属催化反应理论探索及各种新催化体系的建立,过渡金属催化肟及其衍生物进行胺化反应、环化反应以及偶联反应等构筑新的碳碳键、碳氮键等方面取得了长足进展。本论文在综述以上反应进展基础上,发展了铜催化酮肟还原酰化合成烯酰胺的反应和铜催化的肟与醛的偶联反应一步合成吡啶类化合物的新反应。
吡啶类化合物在众多的天然产物、药用化合物以及功能材料分子中,有着广泛的应用。尽管已经发展了很多合成吡啶衍生物的方法,寻求官能团容忍度强且原料经济易得的构筑吡啶环的新途径仍是合成化学家们努力探索的方向之一。在讨论以铜催化酮肟化合物的氮氧键断裂,而后乙酸酐酰化下合成烯酰胺反应基础上,结合过渡金属催化肟类化合物反应的理论研究,我们设计以铜催化肟酯的氮氧键断裂与醛试剂进行氮碳键偶联反应,接着其偶联产物继续与另一分子肟发生偶联反应后关环得到目标的三取代毗啶化合物。经实验摸索后实现以上目标,且通过溴化亚铜催化芳环肟酯与各类醛偶联关环反应,合成了一系列吡啶骨架化合物。
我们报道的该新方法对于环状肟酯的反应效果较好,且含有不同取代基(包括氟、硝基等)的芳香醛都可顺利通过反应得到相应的吡啶类化合物。为深入研究该反应的机理,我们同时做了两分子不同肟与醛的交叉偶联反应实验,结合其分析结果与文献报道,我们对此偶联关环反应的机理也进行了描述。总结我们发展的铜催化肟与醛偶联合成吡啶化合物的新方法,不仅降低了反应的经济成本,而且以环境友好的铜盐做催化剂,符合当前发展绿色化学的前景,操作更简便且官能团容忍性强。
As one of important classess of nitrogen-containing compounds, oximes and their derivatives play important roles on synthetic amine, drug intermediates and other active biological compounds. At the same time oximes have very wide range of uses in the protection and deprotection of aldehydes and ketones, Beckmann rearrangement, and aldoxime dehydration to synthesize nitriles. Recently with the establishment of theoretical exploration and new catalytic system of transition metal catalyzed reactions, considerable progress has been made on transition metal catalyzed oximes and derivatives amination reactions, cyclization reactions and coupling reactions to build new C-C and C-N bonds. Learning the progresses of these reactions, combined with our development of reductive acylation of ketoximes with NaHSO3to synthesis enamide, the thesis highlighted our new method of copper-catalyzed coupling of oxime acetates with aldehydes for synthesis of pyridines.
Pyridines have a wide range of applications in many natural products, medicinal compounds and functional materials molecular. Although many synthetic methods of pyridines have been developed, to seek a new way with strong tolerance of functional groups, the raw material easily obtained to synthesis pyridine is still one of the synthetic directions chemists are trying to explore. After we discuss the progress of CuI-catalyzed the N-O cleavage of oximes to form enamides under the acylation of Ac2O, combined with the theoretical studies of the reactions of transition metal catalyzed oxime compounds, we designed to the new coupling reactions of copper-catalyzed oxime acetate and aldehyde followed by couping and cyclization of previous product and another molecule oxime to prepare tri-substituted pyridine compounds. Fortunately, we achieved the above objectives with experiments, and synthesized of a series of pyridine compounds with aromatic ring oxime acetates and various aldehydes in the presence of copper bromide.
Our developed new method, is more suitable to cyclic keoxime acetates. And aromatic aldehydes containing different substituent groups (including fluoro, nitro, etc.) can be smoothly passed through the approach to give the corresponding pyridine compounds. For in depth study of the mechanism of this reaction, we experimented the coupling reactions of two different molecules oxime acetates and aldehydes, and then this coupling ring closure reaction mechanism had been speculated combined with the results of the analysis and relatedreportes in the literature. In summary, our reported method, copper-catalyzed coupling reactions of oxime acetates and aldehyde to synthesize pyridine compounds, not only reduces the economic cost, operating easier with good functional group tolerance, but also uses environmental friendliness copper salt catalyst, in line with the current development of green chemistry prospects.
吡啶类化合物在众多的天然产物、药用化合物以及功能材料分子中,有着广泛的应用。尽管已经发展了很多合成吡啶衍生物的方法,寻求官能团容忍度强且原料经济易得的构筑吡啶环的新途径仍是合成化学家们努力探索的方向之一。在讨论以铜催化酮肟化合物的氮氧键断裂,而后乙酸酐酰化下合成烯酰胺反应基础上,结合过渡金属催化肟类化合物反应的理论研究,我们设计以铜催化肟酯的氮氧键断裂与醛试剂进行氮碳键偶联反应,接着其偶联产物继续与另一分子肟发生偶联反应后关环得到目标的三取代毗啶化合物。经实验摸索后实现以上目标,且通过溴化亚铜催化芳环肟酯与各类醛偶联关环反应,合成了一系列吡啶骨架化合物。
我们报道的该新方法对于环状肟酯的反应效果较好,且含有不同取代基(包括氟、硝基等)的芳香醛都可顺利通过反应得到相应的吡啶类化合物。为深入研究该反应的机理,我们同时做了两分子不同肟与醛的交叉偶联反应实验,结合其分析结果与文献报道,我们对此偶联关环反应的机理也进行了描述。总结我们发展的铜催化肟与醛偶联合成吡啶化合物的新方法,不仅降低了反应的经济成本,而且以环境友好的铜盐做催化剂,符合当前发展绿色化学的前景,操作更简便且官能团容忍性强。
As one of important classess of nitrogen-containing compounds, oximes and their derivatives play important roles on synthetic amine, drug intermediates and other active biological compounds. At the same time oximes have very wide range of uses in the protection and deprotection of aldehydes and ketones, Beckmann rearrangement, and aldoxime dehydration to synthesize nitriles. Recently with the establishment of theoretical exploration and new catalytic system of transition metal catalyzed reactions, considerable progress has been made on transition metal catalyzed oximes and derivatives amination reactions, cyclization reactions and coupling reactions to build new C-C and C-N bonds. Learning the progresses of these reactions, combined with our development of reductive acylation of ketoximes with NaHSO3to synthesis enamide, the thesis highlighted our new method of copper-catalyzed coupling of oxime acetates with aldehydes for synthesis of pyridines.
Pyridines have a wide range of applications in many natural products, medicinal compounds and functional materials molecular. Although many synthetic methods of pyridines have been developed, to seek a new way with strong tolerance of functional groups, the raw material easily obtained to synthesis pyridine is still one of the synthetic directions chemists are trying to explore. After we discuss the progress of CuI-catalyzed the N-O cleavage of oximes to form enamides under the acylation of Ac2O, combined with the theoretical studies of the reactions of transition metal catalyzed oxime compounds, we designed to the new coupling reactions of copper-catalyzed oxime acetate and aldehyde followed by couping and cyclization of previous product and another molecule oxime to prepare tri-substituted pyridine compounds. Fortunately, we achieved the above objectives with experiments, and synthesized of a series of pyridine compounds with aromatic ring oxime acetates and various aldehydes in the presence of copper bromide.
Our developed new method, is more suitable to cyclic keoxime acetates. And aromatic aldehydes containing different substituent groups (including fluoro, nitro, etc.) can be smoothly passed through the approach to give the corresponding pyridine compounds. For in depth study of the mechanism of this reaction, we experimented the coupling reactions of two different molecules oxime acetates and aldehydes, and then this coupling ring closure reaction mechanism had been speculated combined with the results of the analysis and relatedreportes in the literature. In summary, our reported method, copper-catalyzed coupling reactions of oxime acetates and aldehyde to synthesize pyridine compounds, not only reduces the economic cost, operating easier with good functional group tolerance, but also uses environmental friendliness copper salt catalyst, in line with the current development of green chemistry prospects.
引文
[1](a)SukhorukoV,A.Y.;Ioffe,S.L.Chem.Rev. 2011,111,5004;(b)Alonso,D.A.;Najera, C.Chem.Soc.Rev.2010,39,2891;(c)Himo,F.;Lovell,T.;Hilgraf,R.;Rostovtsev,,V.V.; Noodleman,L.;Sharpless,K.B.;Fokin,V. V. J.An.Chem.Soc.2005,127,210;(d) Narasaka,K.;Kitamura,M.Eur.J. Org.Chem.2005,4505;(e)Narasaka, K.Pure Appl. Chem.2002,74,143.
[2](a)Ganguly,N.C.;Mondal,P.Synthesis 2010,3705;(c)Ramalingan,C.;Park,Y.-T.J. Org.Chem.2007,72,4536;(d)Hashimoto,M.;Obora,Y;Sakaguchi,S.;Ishii,Y.J.Org. Chem.2008,73,2894.
[3](a)Augustine,J.K.;Atta,R.N.;Ramappa,B.K.;Boodappa,C.Synlett.2009,3378;(b) Zhu,J.-L.;Lee,F.-Y.;Wu,J.-D.;Kuo,C.-W:;Shia,K.-S.Synlett.2007,1317;(c)Choi,E.; Lee,C.;Na,Y;Chang,S.Org.Lett.2002,4,2369;(d)De Luca,L.;Giacomelli,G; Porcheddu,A.J. Org.Chem.2002,67,6272.
[4](a)Buchwald,S.L.;Mauger,C.;Mignani,G;Seholzc,U.Adv.Synth.Catal.2006,348, 23.
[5](a)Hartwig,J.F. Synlett.2006,9,1283;(b)Hartwig,J.F.Compr.Coord.Chem.Ⅱ2004,9, 369.
[6](a)Lam,P.Y S.;Vincent,G;Bonne,D.;Clark,C.G. Tetrahedron Lett.2003,44,4927; (b)Lam,P.Y S.;Bonne,D.;Vincent,G.;Clark,C.G.;Combs,A.P.Tetrahedron Lett. 2003,44,1691;(c)Chan,D.M.T.;Monaco,K.L.;Li,R.;Bonne,D.;Clark,C.G.;Lam, P.Y.S.Tetrahedron Lett.2003,44,3863;(d)Lam,P.Y.S.;Vincent,G.;Bonne,D.;Clark, C.G.Terahedron Lett.2002,43,3091;(e)Lam,P.Y S.;Vicent,G.;Clark,C.G.; Deudon,S.;Jadhav,P.K.Tetrahedron Lett.2001,42,3415;(f)Lam,P.Y S.;C1ark,C.G.; Saubern,S.;Adams,J.;Averill,K.M.;Chan,D.M.T.;Combs,A.Synlett 2000,5,674; (g)Antilla,J.C.;Buchwald,S.L.Org.Lett 2001,3,2077;(h)Herradura,P.S.;Pendola, K.A.;Guy,R.K.Org.Lett. 2000,2,2019;(i)Collman,J.P.;Zhong,M.Org.Lett. 2000, 2,1233;(j)Chan,D.M.T.;Monaco,K.L.;Wang,R.-P.;Winters,M.P.Tetrahedron Lett. 1998,39,2933;(k)Evans,D.A.;Katz,J.L.;West,T.R. Tetrahedron Lett.1998,39, 2937.
[7](a)Feng,X.-H.;Zhang,G.-Z.;Chen,C.-Q.;Yang,M.-Y;Xu,X.-Y.;Huang,G.-S.Synth. Commun.2009,39,1768;(b)Abdelselam,A.;Meyer,A.G.;Tuck,K.L.Synlett 2009, 955.
[8]Prithwiraj,D.;Nonappa;Pandurangan,K.;Maitra,U.;Wailes,S.Org.Lett. 2007,9,2767.
[9](a)Nugent,T.C.;El-Shazly,M.Adv.Synth.Catal.2010,352,753;(b)Zhang,X.;Huang, K.;Hou,G.;Cao,B.;Zhang,X.Angew.Chem.,Int.Ed.2010,49,6421;(c)Erre-G.; Enthaler,S.;Junge,K;Addis,D.;Beller,M.Adv.Synth.Catal.2009,351,1437;(d)Shi, L.;Wang,X.;Sandoval,C.A.;Wang,Z.;Li,H.;Wu,J.;Yu,L.;Ding,K.Chem.;Eur.J. 2009,15,9855;(e)Imamoto,T.;Itoh,T.;Yoshida,K.;Gridnev,I.D.Chem.Asian J. 2008,3,1636;(f)Hu,A.G.;Fu,Y.;Xie,J.;Zhu,H.;Wang,L.X.;Zhou,Q.-L.Angew. Chem.,Int.Ed.2002,41,2348;(g)Gridnev,I.D.;Yasutake,M.;Higashi,N.;Imamoto,T. J.Am.Chem.Soc.2001,123,5268.
[10](a)Chang,L.;Kuang,Y;Qin,B.;Zhou,X.;Liu,X.;Lin,L.;Feng,X.Org.Lett.2010, 12,2214;(b)Matsubara,R.;Kobayashi,S.Acc.Chem.Res.2008,41,292;(c)Terada, M.;Sorimachi,K.J.Am.Chem.Soc.2007,129,292;(d)Jia,Y.-X.;Zhong,J.;Zhu,S.-F.; Zhang,C.-M.;Zhou,Q.-L.Angew.Chem.,Int.Ed.2007,46,5565;(e)Terada,M.; Machioka,K.;Sorimachi,K.Angew.Chem.,Int.Ed.2006,45,2254.
[11]Tschaen,D.M.;Abramso,L.;Cai,D.;Richard,D.;Dolling,U.;Frey,L.;Karady,S.,;Shi, Y.;Verhoeven,T.R.J.Org.Chem.1995,60,4324-4330.
[12]Mecozzi,T.;Petrini,M.A.Synlett.2000,73
[13]Villa,M.V J.;Targett,S.M.;Marquez,R.,Org.Lett.2007,9,1631.
[14]Guin,J,;Muck-Lichtenfeld,C.;Grimme,S.;Studer,A.J.Am.Chem.Soc.2007,129, 4498-4503
[15]Elaridi,J.;Thaqi,A.;Prosser,A.;Jackson,W.R.;Robinson A.J.Tetrahedron: Asymmetry 2005,16,1309
[16]Chen,J.;Zhang,W.;Geng,H.;Li,.W.;Hou,G,;Lei,A.;Zhang,X.Angew. Chem.Int.Ed. 2009,48,800-802.
[17]Suen,Y. H.;Horeau,A.;Kagan,H.B[J].Bull. Soc.Chim.Fr.1965,5,1454.
[18]Genovino,J.;Lagu,B.;Wang,Y.;Toure,B.B.Chem.Commun.,2012,48,6735-6737.
[19]Fulrstner,A.;Brehm,C.;Cancho-Grande,Y Org.Lett.2001,3,3955.
[20]Bayer,A.;Maier,M.E.Tetrahedron.,2004,43,6665-6677.
[21]Burk,M.J.;Wang,Y M.;Lee,J.R.J,Am.Chem.Soc.1996,118,5142-5143
[22]Michel,B.;Robert,M.H.;Adriaan,J.M.;Andre,V.;,Johannes,G. V.;Feringa,B.L.-Adv. Synth.Catal.2002,344,1003-1007.
[23]Enthaler,S.;Hagemann,B.;Junge,K.;Erre,G.;Beller,M.Eur.J.Org.Chem.2006,2912.
[24]Savarin,C.G.;Boice,G N.;Murry,J.A.;Corley,E.;DiMichele,L.;Hughes,D.Org.Lett. 2006,8,3903.
[25]O'Shea,P.D.;Gauvreau,D.;Gosselin,F.;Hughes,G.;Nadeau,C.;Roy,A.;Shultz,C.S. J,Org.Chem.2009,74,4547-4553.
[26](a)Van Well,R.M.;Overkleeft,H.S.;van Boom,J.H.;Coop,A.;Wang,J.B.;Wang, H.;van der Marel,G. A.;Overhand,M.Eur.Org.Chem.2003,1704;(b)Dussault,P. H.;Xu,C.Tetrahedron Lett.2004,45,7455.
[27]Brettle, R.;Mosedale, A. J. J. Chem. Soc., Perkin Trans.11988,2,185.
[28]Rigby, J. H.; Balasubramanian, N. J. Org. Chem.1984,49,4571-4572.
[29]Rigby, J. H.; Balasubramanian, N. J. Org. Chem.1989,54,224-228.
[30]Snider, B. B.; Song, F. Org. Lett.2000,2,407-408.
[31]Stefanuti, I.; Smith, S. A.; Taylor R. J. K. Tetrahedron Lett.2000,41,3735-3738.
[32](a) Palomo, C.; Aizpurua, J. M.; Legido, M.; Picard, J. P.; Dunogues,J.; Constantieux, T. Tetrahedron Lett.1992,33,3903; (b) Cuevas, J.-c.;Patil, P.; Snieckus, V. Tetrahedron Lett.1989,30,5841.
[33]Hosokawa, T.; Takano, M.; Kuroki, Y.; Murahashi, S.-I. Tetrahedron Lett.1992,33, 6643.
[34]Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett.1991,1443.
[35]Shen, R.;; Porco, J. A. Jr. Org. Lett.2000,2,1333.
[36]Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc.1997,119,10539.
[37](a) Allred, G D.; Liebeskind, L. S. J. Am. Chem. Soc.1996,118,2748; (b) Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem.1997,62,2312.
[38]Han, C.; Shen, R.; Su, S.; Porco, J. A. Jr. Org. Lett.2004,6,27-30.
[39](a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc.2002,124,7421; (b) Kwong,F. Y.; Buchwald, S. L. Org. Lett.2003,5,793; (c) Klapars, A.; ntilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc.2001,123,7727.
[40]Jiang, L.; Job, G. E.; Klapars, A.; Buchwald S. L. Org. Lett.2003,5,3667-3669.
[41]Pan, X.; Cai, Q.; Ma D. Org. Lett.2004,6,1809.
[42]Coleman, R. S.; Liu, P. Org. Lett.2004,6,577.
[43]Cesati III, R. R.; Dwyer, G.; Jones, R. C.; Hayes, M. P.; Yalamanchili, P.; Casebier, D. S. Org. Lett.2007,9,5617-5620.
[44]Bolshan, Y.; Batey, R. A. Angew. Chem. Int. Ed.2008,47,2109-2112.
[45](a) Lam, P. Y. S.; Vincent, G.; Bonne, D.; Clark, C. G Tetrahedron Lett.2003,44,4927-4931.
[46]Brice, J. L.; Meerdink, J. E.; Stahl, S. S. Org. Lett.,2004,6,1845.
[47]Kozawa, Y.; Mori, M. Tetrahedron Lett.2002,43,111-114.
[48]Wallace, D. J.; Klauber, D. J.; Chen,C.; Volante, R. P. Org. Lett.,2003,5,4749-4752.
[49]Klapars, A.; Campos, K. R.; Chen, C.; Volante, R. P. Org. Lett.,2005,6,1185-1188.
[50]Hosokawa,T.; Takano, M.; Kuroki, Y.; Murahashi, S. I. Tetrahedron Lett.1992,33, 6643-6646.
[51]Timokhin, V.I.; Anastasi, N. R.; Stahl, S. S. J. Am. Chem. Soc.2003,125,12996-12997.
[52]Brice, J. L.; Meerdink, J. E.; Stahl, S. S. Org. Lett.2004,6,1845-1848.
[53]Lee, J. M.; Ahn, D.; Jung, D. Y.; Lee, J.; Do, Y.; Kim, S. K.; Chang, S. J. Am. Chem. Soc. 2006,128,12594-12962.
[54]Liu, X.; Hii, K. K. Eur. J. Org. Chem.2010,5181-5189.
[55](a) H. Doucet, Z. Kabouche, C. Bruneau, P. H. Dixneuf, J. Organomet. Chem.1997,551, 151-157; b) T. Mitsudo, Y. Hori,Y. Watanabe, J. Org. Chem.1985,50,1566-1568; c) L. J.Gooβn, J. Paetzold, Chem. Commun.2003,706-707.
[56](a) Bassetti, M.; Floris, B. J. Chem. Soc. Perkin Trans.21988,227-233; b) Suzuki,T.; Makoto, T.; Wakatsuki, Y. Org. Lett.2001,5,735-737.
[57](a) Pholki, F.; Doye, S. Chem. Soc. Rev.2003,32,104-114; b) Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem. Int. Ed.2004,43,3368-3398.
[58]Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc. Chem. Commun.1995, 413-414.
[59]Gooβn, L. J.; Rauhaus, J. E.; Deng G. Angew. Chem. Int. Ed.2005,44,4042-4045.
[60]Goossen, L. J.; Blanchot, M.; Brinkmann, C; Goossen, K.; Karch, R.; Rivas-Nass, A. J. Org. Chem.2006,71,9506-9509.
[61]Gooβn, L. J.; Salih, K. S. M.; Blanchot, M. Angew. Chem. Int. Ed.2008,47,8492-8495.
[62]Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc.Chem. Commun.1995, 413-414.
[63](a) Bruneau, C.; Dixneuf, P. H. Angew. Chem. Int. Ed.2006,45,2176-2203; (b) Rigaut, S.; Touchard, D.; Dixneuf, P. H. Coord. Chem. Rev.2004,248,1585-1601.
[64]Tokunaga, M.; Suzuki, T.; Koga, N.; Fukushima, T.; Horiuchi, A.; Wakatsuki, Y. J. Am.Chem. Soc.2001,123,11917-11924.
[65]Oliv_an, M.; Clot, E.; Eisenstein, O.; Caulton, K. G. Organometallics 1998,17, 3091-3100.
[66]Arndt, M.; Salih, K. S. M.; Fromm, A.; Goossen, L.J.; Menges, F.; Niedner-Schatteburg G. J. Am. Chem. Soc.2011,133,7428-7449.
[67]Salprima, Y. S.; Kuninobu, Y.; K.; Takai, K. Org. Lett.2007,9,5609-5611.
[68]Panda, N.; Mothkuri, R. J. Org. Chem.2012,77,9407-9412.
[69]Boar, R. B.; McGhie, J. F.; Robinson, M.; Barton, D. H. R.; Horwell, D. C.; Stick, R. V. J. Chem. Soc., Perkin Trans.11975,1237-1242.
[70]Barton, D. H. R.; Zard, S. Z.J. Chem. Soc., Perkin Trans.11985,2191.
[71]Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem.1998,63,6084.
[72]Zhu, G.; Casalnuovo, A. L.; Zhang, X. J. Org. Chem.1998,63,8100-8101.
[73]Allwein, S. P.; McWilliams, J. C.; Secord, E. A.; Mowrey, D. R. a; Nelsona T. D.; Kress, M. H. Tetrahedron Lett.2006,47,6409.
[74]Zhao, H.; Vandenbossche, C. P.; Koenig, S. G.; Singh, S. P.; Bakale, R. P. Org. Lett.2008, 10,505-507.
[75](a)Burgos,A.;Bertrand,B.;Roussiasse,S.;Pluvie,J.-F.;Blanchet,S.;Martin,J.;Perrin, F.;Bourdeau,F.U.S.Patent 2007129573,2007;(b)Bertrand,B.;Blanchet,S.;Burgos, A.;Martin,J.;Perrin,F.;Roussiasse,S.;Derrien,Y U.S.Patent 2007191640,2007.
[76]Guan,Z.-H.;Huang,K.;Yu,S.;Zhang,X.Org.Lett. 2009,11,481-483.
[77](a)Smith,L.I.;Opie,J.W.Organic Synthesis;Wiley:New York,1955;Collect.Vol.Ⅲ, 56;(b)Kurasawa,Y.;Okamoto,Y.;Takada,A.Heterocycles 1984,22,1391.
[78]Reduction of oximes to imilies with Ti(Ⅲ)or Cr(Ⅱ)salts was also reported,see:(a)Boar, R.B.;McGhie,J.F.;Robinson,M.;Barton,D.H.R.;Horwell,D.C.;Stick,R.V. J. Chem.Soc.,Perkin Ⅰ1975,1237;(b)Barton,D.H.R.;Bowles,T.;Husinec,S.;Forbes,J. E.;Llobera,A.;Porter,A.E.A.;Zard,S.Z.Tetrahedron Lett. 1988,29,3343.
[79]Tang,W.;Capacci,A.;Sarvestani,M.;Wei,X.;Yee,N.K.;Senanayake,C.H.J. Org. Chem.2009,74,9528-9530.
[80]Comstock,W.J.Am.Chem.J.19,485(1897).
[81]Bryson,A.;Dmyer,F.P.J.Roy.SOC.N.S.Wales,74,455,171(1940).
[82]Field,L.;Hughmark,P.B.;Shumaker,S.H.;Marshall,W.S.J.Am.Chem.Soc.1961, 83.1983.
[83](a)Sato,O.;Ikushima,Y;Yokoyama,T.J. Org.Chem.1998,63,9100-9102;(b) IKushima,Y.;Hatakeda,K.;Sato,O.;Yokoyama, T.;Arai,M.J.Am.Chem.Soc.2000, 122,1908-1918.
[84]Peng,J.;Deng,Y.Tetrahedron Lett. 2001,42,403-405.
[85]Ren,R.X.;Zueva,L.D.;Ou,W. Tetrahedron Lett. 2001,42,8441-8443.
[86]Ramalingan,C.;Park,Y,J.Org.Chem.2007,72,4536-4538..
[87]HaShimoto,M.;Obora,Y;Sakaguchi,S.;Ishii,Y.J.Org.Chem.2008,73,2894-2897.
[88]Mishra,A.;Ali,A.;Upreti,S.;Gupta,R.Inorganic Chemistry 2008,47,154-161.
[89]Park,S.;Choi,Y;Han,H.;Yang,S.H.;Chang,S.Chem.Commun.2003,1936-1937.
[90]Owston,N.A.;Parker,A.J.;Williams,J.M.J.Org.Lett.,2007,9,73-75.
[91](a)Fujita,K.;Yamaguchi,R.Synlett 2005,560-571;(b)Suzuki,T.;Morita,K.;Tsuchida, M.;Hiroi,K.J.Org.Chem.2003,68,1601-1602.
[92]Owston,N.A.;Parker,A.J.;Williams,J.M.J.Org.Lett.,2007,9,3599-3601.
[93]Fujiwara,H.;Ogasawara,Y.;Yamaguchi,K.;Mizuno,N.Angew. Chem.Int.Ed.2007,46 5202-5205.
[94]Fujiwara,H.;Ogasawara,Y.;Kotani,M.;Yamaguchi,K.;Mizuno,N.Chem.Asian J. 2008,3,1715.
[95]Kim,M.;Lee,J.;Lee,H.;Chang,S.Adv.Synth.Catal. 2009,351,1807-1812.
[96]Lee,J.;Kim,M.;Chang,S.;Lee,H.Org.Lett,2009,11,5598-5601.
[97]Ram6n,R.S.;Bosson,J.;Diz-Gonzalez,S.;Marion,N.;Nolan,S.P.J.Org.Chem.2010, 75,11967-1202.
[98]Tsutsui,H.;Narasaka,K.Chem.Lett.1999,45.
[99](a)Tsutsui,H.;Narasaka,K.Chem.Lett.2001,526-527.;(b)Narasaka,K.Pure Appl. Chem.2002,74,143-149.
[100]M.Kitamura,S.Zaman,K.Narasaka,Synlett 2001,974-976;S.M.Zaman,K. Kitamura,K.Narasaka,Bull.Chem.Soc.Jpn.2003,76,1055-1062.
[101]Sakoda,K.;Mihara,J.;Ichikawa,J.Chem.Commun.2005,4684-4686.
[102]Ichikawa,J.;Nadano,R.;Ito,N.Chem.Commun.2006,4425.4427.
[103]Zaman,S.;Mitsuru,K.;Abell,A.D.Org.Lett.,2005,7,609-611.
[104]Kamijo,S.;Yamamoto,Y. Chem.Asian J. 2007,2,568-578.
[105]Tan,Y.;Hartwig,J.F.J.Am.Chem.Soc.2010,132,3676-3677.
[106]Faulkner,A.;Bower,J.F. Angew. Chem.Int.Ed.2012,51,1675-1679.
[107]Parthasarathy,K.;Jeganmohan,M.;Cheng,C.Org.Lett.,2008,10,325-328.
[108]Martin,R.M.;Bergman,R.G.;Ellman,J.A.,Org.Chem.2012,77,2501-2507,
[109]Too,P.C.;Wang,Y.;Chiba,S.Org.Lett.,2010,12,5688-5691..
[110]Too,P.C.;Chua,S.H.;Wong,S.H.;Chiba,S.J.Org.Chem.2011,76,6159-6168.
[111]Hyster,T.K.;Rovis,T. Chem.Commun.,2000,47,11846-11848.
[112]Zhang,X.;Chen,D.;Zhao,M.;Zhao,J.;Jia,A.;Li,X.Adv.Synth.Catal.2011,353, 719.723.
[113]Zheng,L.;Ju,J.;Bin,Y.;Hua,R.J.Org.Chem.2012,77,5794-5800.
[114]Gerfaud,T.;Neuville,L.;Zhu,J.Angew. Chem.Int.Ed.2009,48,572-577.
[115](a)Ackermann,L.;Fenner,S.Org.Lett.2011,13,6548-6551;(b)Kornhaaβ,C.;Li,J.; Ackermann,L.J.Org.Chem.2012,77,9190-9198.
[116]Liu,S.;Yu,Y;Liebeskind,L.S.Org.Lett.,2007,9,1947-1950.
[117]Liu,S.;Liebeskind,L.S.J.Am.Chem.Soc.2008,130,6918-6919.
[118]Coffen,D.L.;Schaer,B.;Bizzarro,F.T.;Cheung,J.B.J.Org.Chem.1984,49, 296.300.
[119]De,P.;Nonappa,;Pandurangan,K.;Maitra,U.;Wailes,S.Org.Lett.,2007, 9,2767.2770.
[120]Feng,X.-H.;Zhang,G-Z.;Chen,C.-Q.;Yang,M.-Y;Xu,X.-Y;Huang,G.-S.Synth. Commun.2009,39,1768.
[121]Ali,A.;Meyer,A.G;Tuck,K.L.Synlett 2009,955.
[122]Udd,S.;Jokela,R.;Franzen,R.;Tois,J.Tetrahedron Lett.2006,47,8247.
[123]Wang,L.;Huang,C.;Cai,C.Catatysis Comm.2010,11,532.
[124]Maimone,T.J.;Buchwald,S.L.J.Am.Chem.Soc.2010,132,9990-9991.
[125]Desai,L.V;Hull,K.L.;Sanford,M.S.J.Am.Chem.Soc.2004,126,9642-9543.
[126]Thu,H.;Yu,W.;Che,C.J.Am.Chem.Soc.2006,128,9048-9049.
[127]Yu,W.;Sit,W. N.;Lai,K.;Zhou,Z.;Chan,A.S.C.J.Am.Chem.Soc.2008,130, 3304-3306.
[128]Sun,C.;Liu,N.;Li,B.;Yu,D.;Wang,Y;Shi,Z.Org.Lett.,2010,12,184-187.
[129]Ohno,H.;Aso,A.;Kadoh,Y.;Fujii,N.;Tanaka,T.Angew.Chem.Int.Ed.2007,46, 6325-6328.
[130]Thirunavukkarasu,V. S.;Parthasarathy,K.;Cheng,C.H.Angew.Chem.Int. Ed.2008, 47,9462-9465.
[131]Thirunavukkarasu,V. S.;Parthasarathy,K.;Cheng,C.H.Chem.Eur.J. 2010,16, 1436.1440.
[132]Thirunavukkarasu,V. S.;Cheng,C.Chem.Eur.J. 2011,17,14723-14726
[1]Carbery, D. R. Org. Biomol. Chem.2008,6,3455-3460.
[2](a) Stevenson, P. J.; Graham, I. ARKIVOC 2003,7,139-144; (b) Gaulon, C.; Dhal, R.; Chapin, T.; Maisonneuve, V.; Dujardin, G. J. Org. Chem.2004,69,4192-4202.
[3]Willans, C. E.; Mulders, J. M. C. A.; de Vries, J. G.; de Vries, A. H. M. J. Organomet. Chem.2003,687,494-497.
[4]Matsubara, R.; Nakamura, Y.; Kobayashi, S. Angew. Chem. Int. Ed.2004,43, 1679-1681.
[5](a) Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem.1998,63,6084; (b) Zhu, G.; Casalnuovo, A. L.; Zhang, X. J. Org. Chem.1998,63,8100-8101.
[6]Tang, W.;Capacci, A.; Sarvestani, M.; Wei, X.; Yee, N. K.; Senanayake, C. H. J. Org. Chem.2009,74,9528-9530.
[7](a) Burgos, A.; Bertrand, B.; Roussiasse, S.; Pluvie, J.-F.; Blanchet, S.; Martin, J.; Perrin, F.; Bourdeau, F. U.S. Patent 2007129573,2007; (b) Bertrand, B.; Blanchet, S.; Burgos, A.; Martin, J.; Perrin, F.; Roussiasse, S.; Derrien, Y. U.S. Patent 2007191640,2007;(c) Guan, Z.-H.; Huang, K.; Yu, S.; Zhang, X. Org. Lett.2009,11,481-483.
[8]Reduction of oximes to imines with Ti(III) or Cr(II) salts was also reported, see:(a) Boar, R. B.; McGhie, J. F.; Robinson, M.; Barton, D. H. R.; Horwell, D. C.; Stick, R. V. J. Chem. Soc., Perkin I 1975,1237; (b) Barton, D. H. R.; Bowles, T.; Husinec, S.; Forbes, J. E.; Llobera, A.; Porter, A. E. A.; Zard, S. Z. Tetrahedron Lett.1988,29,3343.
[9](a) Smith, L. I.; Opie, J.W. Organic Synthesis; Wiley:New York,1955; Collect. Vol. Ⅲ,56; (b) Kurasawa, Y.; Okamoto, Y.; Takada, A. Heterocycles 1984,22, 1391.
[10](a) Yang, S. H.; Chang, S. Org. Lett.,2001,3,4209-4211; (b) Choi, E.; Lee, C.; Na, Y.;and Chang, S. Org. Lett,2002,4,2369-2371.
[11](a) Narasaka, K. Pure Appl. Chem.,2002,74,143-149; (b) Narasaka, K.; Kitamura, M. Eur. J. Org. Chem.2005,4505-4519.
[12]Guan, Z.; Zhang, Z.; Ren, Z.; Wang, Y; Zhang, X. J. Org. Chem.,2011,76,339-341；关正辉、任智卉、张志远、杨秉勤。一种烯酰胺类化合物的合成方法,中国发明专利：公开号：CN101875590A,2010.11.03
[13](a) Ferreira, C. M. P.; Guedes da Silva, M. F. C.; Kukushkin, V. Y.; Frausto da Silva, J. J. R.; Pombeiro, A. J. L. J. Chem. Soc., Dalton Trans.1998,325; (b) M. Kitamura, S. Zaman, K. Narasaka, Synlett 2001,974-976; (c) S. M. Zaman, K. Kitamura,K.Narasaka,Bull.Chem.Soc.Jpn.2003,76,1055-1062.
[14](a)Boivin,J.;Schiano,A.-M.;Zard,S.Z.;Zhang,H.Tetrahedron Lett.1999,40, 4531-4534;(b)Narasaka K.;Kitamura,M.Eur.J.Org.Chem.2005,4505-4519.
[15](a)Ullmann,F.Ber.Dtsch.Chem.Ges.1903,36,2382;(b)Goldberg,I.Ber. Dtsch.Chem.Ges.1906,39,1691-1692.
[16](a)Krause,N.Modern Organocopper Chemistry; Wiley-VCH: Weinheim, Germany,2002;(b)Ley,S.V.;Thomas,A.W.Angew. Chem.,Int.Ed.2003,42, 5400-5449.(c)Monnier,F.;Taillefer,M.Angew.Chem.,Int.Ed.2009,48, 6954-6971.(d)Hassan,J.;Sevignon,M.;Gozzi,C.;Schulz,E.;Lemaire,M. Chem.Rev.2002,102,1359-1469.(e)Chemler,S.R.;Fuller,P.H.Chem.Soc. Rev.2007,36,1153-1160.(f)Beletskaya,I.P.;Cheprakov,A.V Coord.Chem. Rev.2004,248,2337-2364.(g)Finet,J.-P.;Fedorov,A.Y;Combes,S.;Boyer,G Curr.Org.Chem.2002,6,597-626.(h)Sperotto,E.;van Klink,G.P.M.;van Koten,G.;de Vries,J.G Dalton Trans.2010,39,10338-10351.(i)Evano,G.; B1anchard,N.;Toumi,M.Chem.Rev.2008,108,3054-3131.
[17](a)Jones,G. O.;Liu,P.;Houk,K.N.;Buchwald,S.L.J.Am.Chem.Soc.2010, J32,6205-6213.(d)Strieter,E.R.;Bhayana,B.;Buchwald,S.L.J.Am.Chem. Soc.2009,131,78-88.(e)Strieter,E.R.;Blackmond,D.G.;Buchwald,S.L.J. Am.Chem.Soc.2005,127,4120-4121;(g)Tye,J.W.;Weng,Z.;Johns,A.M.; Incarvito,C.D.;Hartwig,J.F.J.Am.Chem.Soc.2008,130,9971-9983;(i)Franc, G;Cacciuttolo,Q.;Lefevre,G.;Adamo,C.;Ciofini,I.;Jutand,A.ChemCatChem 2011,3,305-309;(m)Yu,H.-Z.;Jiang,Y-Y;Fu,Y.;Liu,L.,J.Am.Chem.Soc. 2010,132,18078-18091;(o)Zhang,S.-L.;Liu,L.;Fu,Y;Guo,Q.-X. Organometallics 2007,26,4546-4554;
[18](a)Paine,A.J.J.Am.Chem.Soc.1987,109,1496-1502;(b)Mansour,M.; Giacovazzi,R.;Ouali,A.;Taillefer,M.;Jutand,A.Chem.Commun.2008, 6051-6053;(c)Franc,G.;Jutand,A.Dalton Trans.2010,39,7873-7875;(d) Huang,Z.;Hartwig,J.F.Angew.Chem.,Int.Ed.2012,51,1028-1032;(e)He,C.; Zhang,G.;Ke,J.;Zhang,H.;Miller,J.T.;Kropf, A.J.;Lei,A.J.Am.Chem.Soc. 2013 135,488-493
[19](a)Wang,W.;Li,J.;Wang,K.;Smirnova,T.I.;Oldfield,E.J.Am.Chem.Soc. 2011,133,6525.(b)Henry,G. D.Tetrahedron 2004,60,6043.(d)Michael,J.P. Nat. Prod. Rep.2005,22,627.(c)Carey,J.S.;Laffan,D.;Thomson,C.;Williams, M.T.Org.Binomol.Chem.2006,4,2337.
[20](a)Heller,B.;Hapke,M.Chem.Soc.Rev.2007,36,1085.(b)Wang,Y.-F.;Chiba, S.J. Am. Chem. Soc.2009,131,12570. (c) Movassaghi, M.; Hill, M. D.; Ahmad, O. K. J. Am. Chem. Soc.2007,129,10096. (d) Yoshida, K.; Kawagoe, F.; Hayashi, K.; Horiuchi, S.; Imamoto, T.; Yanagisawa, A. Org. Lett.2009,11,515. (e) De Paolis, O.; Baffoe, J.; Landge, S. M.; T€or€ok, B. Synthesis 2008,3423.
[21]Guan, Z.-H.; Zhang, Z.-Y; Ren, Z.-H.; Wang, Y.-Y.; Zhang, X. J. Org. Chem. 2011,76,339.
[22](a) Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc.2002,124,2528. (b) Nitta, M.; Iino, Y Bull. Chem. Soc. Jpn.1986,59,2365. (c) Deeming, A. J.; Owen, D. W.; Powell, N. I. J. Organomet. Chem.1990,398,299.
[23]Takai, K.; Katsura, N.; Kunisada, Y. Chem. Commun.2001,1724.
[24]Liu, S.; Liebeskind, L. S.J. Am. Chem. Soc.2008,130,6918.
[2](a)Ganguly,N.C.;Mondal,P.Synthesis 2010,3705;(c)Ramalingan,C.;Park,Y.-T.J. Org.Chem.2007,72,4536;(d)Hashimoto,M.;Obora,Y;Sakaguchi,S.;Ishii,Y.J.Org. Chem.2008,73,2894.
[3](a)Augustine,J.K.;Atta,R.N.;Ramappa,B.K.;Boodappa,C.Synlett.2009,3378;(b) Zhu,J.-L.;Lee,F.-Y.;Wu,J.-D.;Kuo,C.-W:;Shia,K.-S.Synlett.2007,1317;(c)Choi,E.; Lee,C.;Na,Y;Chang,S.Org.Lett.2002,4,2369;(d)De Luca,L.;Giacomelli,G; Porcheddu,A.J. Org.Chem.2002,67,6272.
[4](a)Buchwald,S.L.;Mauger,C.;Mignani,G;Seholzc,U.Adv.Synth.Catal.2006,348, 23.
[5](a)Hartwig,J.F. Synlett.2006,9,1283;(b)Hartwig,J.F.Compr.Coord.Chem.Ⅱ2004,9, 369.
[6](a)Lam,P.Y S.;Vincent,G;Bonne,D.;Clark,C.G. Tetrahedron Lett.2003,44,4927; (b)Lam,P.Y S.;Bonne,D.;Vincent,G.;Clark,C.G.;Combs,A.P.Tetrahedron Lett. 2003,44,1691;(c)Chan,D.M.T.;Monaco,K.L.;Li,R.;Bonne,D.;Clark,C.G.;Lam, P.Y.S.Tetrahedron Lett.2003,44,3863;(d)Lam,P.Y.S.;Vincent,G.;Bonne,D.;Clark, C.G.Terahedron Lett.2002,43,3091;(e)Lam,P.Y S.;Vicent,G.;Clark,C.G.; Deudon,S.;Jadhav,P.K.Tetrahedron Lett.2001,42,3415;(f)Lam,P.Y S.;C1ark,C.G.; Saubern,S.;Adams,J.;Averill,K.M.;Chan,D.M.T.;Combs,A.Synlett 2000,5,674; (g)Antilla,J.C.;Buchwald,S.L.Org.Lett 2001,3,2077;(h)Herradura,P.S.;Pendola, K.A.;Guy,R.K.Org.Lett. 2000,2,2019;(i)Collman,J.P.;Zhong,M.Org.Lett. 2000, 2,1233;(j)Chan,D.M.T.;Monaco,K.L.;Wang,R.-P.;Winters,M.P.Tetrahedron Lett. 1998,39,2933;(k)Evans,D.A.;Katz,J.L.;West,T.R. Tetrahedron Lett.1998,39, 2937.
[7](a)Feng,X.-H.;Zhang,G.-Z.;Chen,C.-Q.;Yang,M.-Y;Xu,X.-Y.;Huang,G.-S.Synth. Commun.2009,39,1768;(b)Abdelselam,A.;Meyer,A.G.;Tuck,K.L.Synlett 2009, 955.
[8]Prithwiraj,D.;Nonappa;Pandurangan,K.;Maitra,U.;Wailes,S.Org.Lett. 2007,9,2767.
[9](a)Nugent,T.C.;El-Shazly,M.Adv.Synth.Catal.2010,352,753;(b)Zhang,X.;Huang, K.;Hou,G.;Cao,B.;Zhang,X.Angew.Chem.,Int.Ed.2010,49,6421;(c)Erre-G.; Enthaler,S.;Junge,K;Addis,D.;Beller,M.Adv.Synth.Catal.2009,351,1437;(d)Shi, L.;Wang,X.;Sandoval,C.A.;Wang,Z.;Li,H.;Wu,J.;Yu,L.;Ding,K.Chem.;Eur.J. 2009,15,9855;(e)Imamoto,T.;Itoh,T.;Yoshida,K.;Gridnev,I.D.Chem.Asian J. 2008,3,1636;(f)Hu,A.G.;Fu,Y.;Xie,J.;Zhu,H.;Wang,L.X.;Zhou,Q.-L.Angew. Chem.,Int.Ed.2002,41,2348;(g)Gridnev,I.D.;Yasutake,M.;Higashi,N.;Imamoto,T. J.Am.Chem.Soc.2001,123,5268.
[10](a)Chang,L.;Kuang,Y;Qin,B.;Zhou,X.;Liu,X.;Lin,L.;Feng,X.Org.Lett.2010, 12,2214;(b)Matsubara,R.;Kobayashi,S.Acc.Chem.Res.2008,41,292;(c)Terada, M.;Sorimachi,K.J.Am.Chem.Soc.2007,129,292;(d)Jia,Y.-X.;Zhong,J.;Zhu,S.-F.; Zhang,C.-M.;Zhou,Q.-L.Angew.Chem.,Int.Ed.2007,46,5565;(e)Terada,M.; Machioka,K.;Sorimachi,K.Angew.Chem.,Int.Ed.2006,45,2254.
[11]Tschaen,D.M.;Abramso,L.;Cai,D.;Richard,D.;Dolling,U.;Frey,L.;Karady,S.,;Shi, Y.;Verhoeven,T.R.J.Org.Chem.1995,60,4324-4330.
[12]Mecozzi,T.;Petrini,M.A.Synlett.2000,73
[13]Villa,M.V J.;Targett,S.M.;Marquez,R.,Org.Lett.2007,9,1631.
[14]Guin,J,;Muck-Lichtenfeld,C.;Grimme,S.;Studer,A.J.Am.Chem.Soc.2007,129, 4498-4503
[15]Elaridi,J.;Thaqi,A.;Prosser,A.;Jackson,W.R.;Robinson A.J.Tetrahedron: Asymmetry 2005,16,1309
[16]Chen,J.;Zhang,W.;Geng,H.;Li,.W.;Hou,G,;Lei,A.;Zhang,X.Angew. Chem.Int.Ed. 2009,48,800-802.
[17]Suen,Y. H.;Horeau,A.;Kagan,H.B[J].Bull. Soc.Chim.Fr.1965,5,1454.
[18]Genovino,J.;Lagu,B.;Wang,Y.;Toure,B.B.Chem.Commun.,2012,48,6735-6737.
[19]Fulrstner,A.;Brehm,C.;Cancho-Grande,Y Org.Lett.2001,3,3955.
[20]Bayer,A.;Maier,M.E.Tetrahedron.,2004,43,6665-6677.
[21]Burk,M.J.;Wang,Y M.;Lee,J.R.J,Am.Chem.Soc.1996,118,5142-5143
[22]Michel,B.;Robert,M.H.;Adriaan,J.M.;Andre,V.;,Johannes,G. V.;Feringa,B.L.-Adv. Synth.Catal.2002,344,1003-1007.
[23]Enthaler,S.;Hagemann,B.;Junge,K.;Erre,G.;Beller,M.Eur.J.Org.Chem.2006,2912.
[24]Savarin,C.G.;Boice,G N.;Murry,J.A.;Corley,E.;DiMichele,L.;Hughes,D.Org.Lett. 2006,8,3903.
[25]O'Shea,P.D.;Gauvreau,D.;Gosselin,F.;Hughes,G.;Nadeau,C.;Roy,A.;Shultz,C.S. J,Org.Chem.2009,74,4547-4553.
[26](a)Van Well,R.M.;Overkleeft,H.S.;van Boom,J.H.;Coop,A.;Wang,J.B.;Wang, H.;van der Marel,G. A.;Overhand,M.Eur.Org.Chem.2003,1704;(b)Dussault,P. H.;Xu,C.Tetrahedron Lett.2004,45,7455.
[27]Brettle, R.;Mosedale, A. J. J. Chem. Soc., Perkin Trans.11988,2,185.
[28]Rigby, J. H.; Balasubramanian, N. J. Org. Chem.1984,49,4571-4572.
[29]Rigby, J. H.; Balasubramanian, N. J. Org. Chem.1989,54,224-228.
[30]Snider, B. B.; Song, F. Org. Lett.2000,2,407-408.
[31]Stefanuti, I.; Smith, S. A.; Taylor R. J. K. Tetrahedron Lett.2000,41,3735-3738.
[32](a) Palomo, C.; Aizpurua, J. M.; Legido, M.; Picard, J. P.; Dunogues,J.; Constantieux, T. Tetrahedron Lett.1992,33,3903; (b) Cuevas, J.-c.;Patil, P.; Snieckus, V. Tetrahedron Lett.1989,30,5841.
[33]Hosokawa, T.; Takano, M.; Kuroki, Y.; Murahashi, S.-I. Tetrahedron Lett.1992,33, 6643.
[34]Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett.1991,1443.
[35]Shen, R.;; Porco, J. A. Jr. Org. Lett.2000,2,1333.
[36]Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc.1997,119,10539.
[37](a) Allred, G D.; Liebeskind, L. S. J. Am. Chem. Soc.1996,118,2748; (b) Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem.1997,62,2312.
[38]Han, C.; Shen, R.; Su, S.; Porco, J. A. Jr. Org. Lett.2004,6,27-30.
[39](a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc.2002,124,7421; (b) Kwong,F. Y.; Buchwald, S. L. Org. Lett.2003,5,793; (c) Klapars, A.; ntilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc.2001,123,7727.
[40]Jiang, L.; Job, G. E.; Klapars, A.; Buchwald S. L. Org. Lett.2003,5,3667-3669.
[41]Pan, X.; Cai, Q.; Ma D. Org. Lett.2004,6,1809.
[42]Coleman, R. S.; Liu, P. Org. Lett.2004,6,577.
[43]Cesati III, R. R.; Dwyer, G.; Jones, R. C.; Hayes, M. P.; Yalamanchili, P.; Casebier, D. S. Org. Lett.2007,9,5617-5620.
[44]Bolshan, Y.; Batey, R. A. Angew. Chem. Int. Ed.2008,47,2109-2112.
[45](a) Lam, P. Y. S.; Vincent, G.; Bonne, D.; Clark, C. G Tetrahedron Lett.2003,44,4927-4931.
[46]Brice, J. L.; Meerdink, J. E.; Stahl, S. S. Org. Lett.,2004,6,1845.
[47]Kozawa, Y.; Mori, M. Tetrahedron Lett.2002,43,111-114.
[48]Wallace, D. J.; Klauber, D. J.; Chen,C.; Volante, R. P. Org. Lett.,2003,5,4749-4752.
[49]Klapars, A.; Campos, K. R.; Chen, C.; Volante, R. P. Org. Lett.,2005,6,1185-1188.
[50]Hosokawa,T.; Takano, M.; Kuroki, Y.; Murahashi, S. I. Tetrahedron Lett.1992,33, 6643-6646.
[51]Timokhin, V.I.; Anastasi, N. R.; Stahl, S. S. J. Am. Chem. Soc.2003,125,12996-12997.
[52]Brice, J. L.; Meerdink, J. E.; Stahl, S. S. Org. Lett.2004,6,1845-1848.
[53]Lee, J. M.; Ahn, D.; Jung, D. Y.; Lee, J.; Do, Y.; Kim, S. K.; Chang, S. J. Am. Chem. Soc. 2006,128,12594-12962.
[54]Liu, X.; Hii, K. K. Eur. J. Org. Chem.2010,5181-5189.
[55](a) H. Doucet, Z. Kabouche, C. Bruneau, P. H. Dixneuf, J. Organomet. Chem.1997,551, 151-157; b) T. Mitsudo, Y. Hori,Y. Watanabe, J. Org. Chem.1985,50,1566-1568; c) L. J.Gooβn, J. Paetzold, Chem. Commun.2003,706-707.
[56](a) Bassetti, M.; Floris, B. J. Chem. Soc. Perkin Trans.21988,227-233; b) Suzuki,T.; Makoto, T.; Wakatsuki, Y. Org. Lett.2001,5,735-737.
[57](a) Pholki, F.; Doye, S. Chem. Soc. Rev.2003,32,104-114; b) Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem. Int. Ed.2004,43,3368-3398.
[58]Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc. Chem. Commun.1995, 413-414.
[59]Gooβn, L. J.; Rauhaus, J. E.; Deng G. Angew. Chem. Int. Ed.2005,44,4042-4045.
[60]Goossen, L. J.; Blanchot, M.; Brinkmann, C; Goossen, K.; Karch, R.; Rivas-Nass, A. J. Org. Chem.2006,71,9506-9509.
[61]Gooβn, L. J.; Salih, K. S. M.; Blanchot, M. Angew. Chem. Int. Ed.2008,47,8492-8495.
[62]Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc.Chem. Commun.1995, 413-414.
[63](a) Bruneau, C.; Dixneuf, P. H. Angew. Chem. Int. Ed.2006,45,2176-2203; (b) Rigaut, S.; Touchard, D.; Dixneuf, P. H. Coord. Chem. Rev.2004,248,1585-1601.
[64]Tokunaga, M.; Suzuki, T.; Koga, N.; Fukushima, T.; Horiuchi, A.; Wakatsuki, Y. J. Am.Chem. Soc.2001,123,11917-11924.
[65]Oliv_an, M.; Clot, E.; Eisenstein, O.; Caulton, K. G. Organometallics 1998,17, 3091-3100.
[66]Arndt, M.; Salih, K. S. M.; Fromm, A.; Goossen, L.J.; Menges, F.; Niedner-Schatteburg G. J. Am. Chem. Soc.2011,133,7428-7449.
[67]Salprima, Y. S.; Kuninobu, Y.; K.; Takai, K. Org. Lett.2007,9,5609-5611.
[68]Panda, N.; Mothkuri, R. J. Org. Chem.2012,77,9407-9412.
[69]Boar, R. B.; McGhie, J. F.; Robinson, M.; Barton, D. H. R.; Horwell, D. C.; Stick, R. V. J. Chem. Soc., Perkin Trans.11975,1237-1242.
[70]Barton, D. H. R.; Zard, S. Z.J. Chem. Soc., Perkin Trans.11985,2191.
[71]Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem.1998,63,6084.
[72]Zhu, G.; Casalnuovo, A. L.; Zhang, X. J. Org. Chem.1998,63,8100-8101.
[73]Allwein, S. P.; McWilliams, J. C.; Secord, E. A.; Mowrey, D. R. a; Nelsona T. D.; Kress, M. H. Tetrahedron Lett.2006,47,6409.
[74]Zhao, H.; Vandenbossche, C. P.; Koenig, S. G.; Singh, S. P.; Bakale, R. P. Org. Lett.2008, 10,505-507.
[75](a)Burgos,A.;Bertrand,B.;Roussiasse,S.;Pluvie,J.-F.;Blanchet,S.;Martin,J.;Perrin, F.;Bourdeau,F.U.S.Patent 2007129573,2007;(b)Bertrand,B.;Blanchet,S.;Burgos, A.;Martin,J.;Perrin,F.;Roussiasse,S.;Derrien,Y U.S.Patent 2007191640,2007.
[76]Guan,Z.-H.;Huang,K.;Yu,S.;Zhang,X.Org.Lett. 2009,11,481-483.
[77](a)Smith,L.I.;Opie,J.W.Organic Synthesis;Wiley:New York,1955;Collect.Vol.Ⅲ, 56;(b)Kurasawa,Y.;Okamoto,Y.;Takada,A.Heterocycles 1984,22,1391.
[78]Reduction of oximes to imilies with Ti(Ⅲ)or Cr(Ⅱ)salts was also reported,see:(a)Boar, R.B.;McGhie,J.F.;Robinson,M.;Barton,D.H.R.;Horwell,D.C.;Stick,R.V. J. Chem.Soc.,Perkin Ⅰ1975,1237;(b)Barton,D.H.R.;Bowles,T.;Husinec,S.;Forbes,J. E.;Llobera,A.;Porter,A.E.A.;Zard,S.Z.Tetrahedron Lett. 1988,29,3343.
[79]Tang,W.;Capacci,A.;Sarvestani,M.;Wei,X.;Yee,N.K.;Senanayake,C.H.J. Org. Chem.2009,74,9528-9530.
[80]Comstock,W.J.Am.Chem.J.19,485(1897).
[81]Bryson,A.;Dmyer,F.P.J.Roy.SOC.N.S.Wales,74,455,171(1940).
[82]Field,L.;Hughmark,P.B.;Shumaker,S.H.;Marshall,W.S.J.Am.Chem.Soc.1961, 83.1983.
[83](a)Sato,O.;Ikushima,Y;Yokoyama,T.J. Org.Chem.1998,63,9100-9102;(b) IKushima,Y.;Hatakeda,K.;Sato,O.;Yokoyama, T.;Arai,M.J.Am.Chem.Soc.2000, 122,1908-1918.
[84]Peng,J.;Deng,Y.Tetrahedron Lett. 2001,42,403-405.
[85]Ren,R.X.;Zueva,L.D.;Ou,W. Tetrahedron Lett. 2001,42,8441-8443.
[86]Ramalingan,C.;Park,Y,J.Org.Chem.2007,72,4536-4538..
[87]HaShimoto,M.;Obora,Y;Sakaguchi,S.;Ishii,Y.J.Org.Chem.2008,73,2894-2897.
[88]Mishra,A.;Ali,A.;Upreti,S.;Gupta,R.Inorganic Chemistry 2008,47,154-161.
[89]Park,S.;Choi,Y;Han,H.;Yang,S.H.;Chang,S.Chem.Commun.2003,1936-1937.
[90]Owston,N.A.;Parker,A.J.;Williams,J.M.J.Org.Lett.,2007,9,73-75.
[91](a)Fujita,K.;Yamaguchi,R.Synlett 2005,560-571;(b)Suzuki,T.;Morita,K.;Tsuchida, M.;Hiroi,K.J.Org.Chem.2003,68,1601-1602.
[92]Owston,N.A.;Parker,A.J.;Williams,J.M.J.Org.Lett.,2007,9,3599-3601.
[93]Fujiwara,H.;Ogasawara,Y.;Yamaguchi,K.;Mizuno,N.Angew. Chem.Int.Ed.2007,46 5202-5205.
[94]Fujiwara,H.;Ogasawara,Y.;Kotani,M.;Yamaguchi,K.;Mizuno,N.Chem.Asian J. 2008,3,1715.
[95]Kim,M.;Lee,J.;Lee,H.;Chang,S.Adv.Synth.Catal. 2009,351,1807-1812.
[96]Lee,J.;Kim,M.;Chang,S.;Lee,H.Org.Lett,2009,11,5598-5601.
[97]Ram6n,R.S.;Bosson,J.;Diz-Gonzalez,S.;Marion,N.;Nolan,S.P.J.Org.Chem.2010, 75,11967-1202.
[98]Tsutsui,H.;Narasaka,K.Chem.Lett.1999,45.
[99](a)Tsutsui,H.;Narasaka,K.Chem.Lett.2001,526-527.;(b)Narasaka,K.Pure Appl. Chem.2002,74,143-149.
[100]M.Kitamura,S.Zaman,K.Narasaka,Synlett 2001,974-976;S.M.Zaman,K. Kitamura,K.Narasaka,Bull.Chem.Soc.Jpn.2003,76,1055-1062.
[101]Sakoda,K.;Mihara,J.;Ichikawa,J.Chem.Commun.2005,4684-4686.
[102]Ichikawa,J.;Nadano,R.;Ito,N.Chem.Commun.2006,4425.4427.
[103]Zaman,S.;Mitsuru,K.;Abell,A.D.Org.Lett.,2005,7,609-611.
[104]Kamijo,S.;Yamamoto,Y. Chem.Asian J. 2007,2,568-578.
[105]Tan,Y.;Hartwig,J.F.J.Am.Chem.Soc.2010,132,3676-3677.
[106]Faulkner,A.;Bower,J.F. Angew. Chem.Int.Ed.2012,51,1675-1679.
[107]Parthasarathy,K.;Jeganmohan,M.;Cheng,C.Org.Lett.,2008,10,325-328.
[108]Martin,R.M.;Bergman,R.G.;Ellman,J.A.,Org.Chem.2012,77,2501-2507,
[109]Too,P.C.;Wang,Y.;Chiba,S.Org.Lett.,2010,12,5688-5691..
[110]Too,P.C.;Chua,S.H.;Wong,S.H.;Chiba,S.J.Org.Chem.2011,76,6159-6168.
[111]Hyster,T.K.;Rovis,T. Chem.Commun.,2000,47,11846-11848.
[112]Zhang,X.;Chen,D.;Zhao,M.;Zhao,J.;Jia,A.;Li,X.Adv.Synth.Catal.2011,353, 719.723.
[113]Zheng,L.;Ju,J.;Bin,Y.;Hua,R.J.Org.Chem.2012,77,5794-5800.
[114]Gerfaud,T.;Neuville,L.;Zhu,J.Angew. Chem.Int.Ed.2009,48,572-577.
[115](a)Ackermann,L.;Fenner,S.Org.Lett.2011,13,6548-6551;(b)Kornhaaβ,C.;Li,J.; Ackermann,L.J.Org.Chem.2012,77,9190-9198.
[116]Liu,S.;Yu,Y;Liebeskind,L.S.Org.Lett.,2007,9,1947-1950.
[117]Liu,S.;Liebeskind,L.S.J.Am.Chem.Soc.2008,130,6918-6919.
[118]Coffen,D.L.;Schaer,B.;Bizzarro,F.T.;Cheung,J.B.J.Org.Chem.1984,49, 296.300.
[119]De,P.;Nonappa,;Pandurangan,K.;Maitra,U.;Wailes,S.Org.Lett.,2007, 9,2767.2770.
[120]Feng,X.-H.;Zhang,G-Z.;Chen,C.-Q.;Yang,M.-Y;Xu,X.-Y;Huang,G.-S.Synth. Commun.2009,39,1768.
[121]Ali,A.;Meyer,A.G;Tuck,K.L.Synlett 2009,955.
[122]Udd,S.;Jokela,R.;Franzen,R.;Tois,J.Tetrahedron Lett.2006,47,8247.
[123]Wang,L.;Huang,C.;Cai,C.Catatysis Comm.2010,11,532.
[124]Maimone,T.J.;Buchwald,S.L.J.Am.Chem.Soc.2010,132,9990-9991.
[125]Desai,L.V;Hull,K.L.;Sanford,M.S.J.Am.Chem.Soc.2004,126,9642-9543.
[126]Thu,H.;Yu,W.;Che,C.J.Am.Chem.Soc.2006,128,9048-9049.
[127]Yu,W.;Sit,W. N.;Lai,K.;Zhou,Z.;Chan,A.S.C.J.Am.Chem.Soc.2008,130, 3304-3306.
[128]Sun,C.;Liu,N.;Li,B.;Yu,D.;Wang,Y;Shi,Z.Org.Lett.,2010,12,184-187.
[129]Ohno,H.;Aso,A.;Kadoh,Y.;Fujii,N.;Tanaka,T.Angew.Chem.Int.Ed.2007,46, 6325-6328.
[130]Thirunavukkarasu,V. S.;Parthasarathy,K.;Cheng,C.H.Angew.Chem.Int. Ed.2008, 47,9462-9465.
[131]Thirunavukkarasu,V. S.;Parthasarathy,K.;Cheng,C.H.Chem.Eur.J. 2010,16, 1436.1440.
[132]Thirunavukkarasu,V. S.;Cheng,C.Chem.Eur.J. 2011,17,14723-14726
[1]Carbery, D. R. Org. Biomol. Chem.2008,6,3455-3460.
[2](a) Stevenson, P. J.; Graham, I. ARKIVOC 2003,7,139-144; (b) Gaulon, C.; Dhal, R.; Chapin, T.; Maisonneuve, V.; Dujardin, G. J. Org. Chem.2004,69,4192-4202.
[3]Willans, C. E.; Mulders, J. M. C. A.; de Vries, J. G.; de Vries, A. H. M. J. Organomet. Chem.2003,687,494-497.
[4]Matsubara, R.; Nakamura, Y.; Kobayashi, S. Angew. Chem. Int. Ed.2004,43, 1679-1681.
[5](a) Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem.1998,63,6084; (b) Zhu, G.; Casalnuovo, A. L.; Zhang, X. J. Org. Chem.1998,63,8100-8101.
[6]Tang, W.;Capacci, A.; Sarvestani, M.; Wei, X.; Yee, N. K.; Senanayake, C. H. J. Org. Chem.2009,74,9528-9530.
[7](a) Burgos, A.; Bertrand, B.; Roussiasse, S.; Pluvie, J.-F.; Blanchet, S.; Martin, J.; Perrin, F.; Bourdeau, F. U.S. Patent 2007129573,2007; (b) Bertrand, B.; Blanchet, S.; Burgos, A.; Martin, J.; Perrin, F.; Roussiasse, S.; Derrien, Y. U.S. Patent 2007191640,2007;(c) Guan, Z.-H.; Huang, K.; Yu, S.; Zhang, X. Org. Lett.2009,11,481-483.
[8]Reduction of oximes to imines with Ti(III) or Cr(II) salts was also reported, see:(a) Boar, R. B.; McGhie, J. F.; Robinson, M.; Barton, D. H. R.; Horwell, D. C.; Stick, R. V. J. Chem. Soc., Perkin I 1975,1237; (b) Barton, D. H. R.; Bowles, T.; Husinec, S.; Forbes, J. E.; Llobera, A.; Porter, A. E. A.; Zard, S. Z. Tetrahedron Lett.1988,29,3343.
[9](a) Smith, L. I.; Opie, J.W. Organic Synthesis; Wiley:New York,1955; Collect. Vol. Ⅲ,56; (b) Kurasawa, Y.; Okamoto, Y.; Takada, A. Heterocycles 1984,22, 1391.
[10](a) Yang, S. H.; Chang, S. Org. Lett.,2001,3,4209-4211; (b) Choi, E.; Lee, C.; Na, Y.;and Chang, S. Org. Lett,2002,4,2369-2371.
[11](a) Narasaka, K. Pure Appl. Chem.,2002,74,143-149; (b) Narasaka, K.; Kitamura, M. Eur. J. Org. Chem.2005,4505-4519.
[12]Guan, Z.; Zhang, Z.; Ren, Z.; Wang, Y; Zhang, X. J. Org. Chem.,2011,76,339-341；关正辉、任智卉、张志远、杨秉勤。一种烯酰胺类化合物的合成方法,中国发明专利：公开号：CN101875590A,2010.11.03
[13](a) Ferreira, C. M. P.; Guedes da Silva, M. F. C.; Kukushkin, V. Y.; Frausto da Silva, J. J. R.; Pombeiro, A. J. L. J. Chem. Soc., Dalton Trans.1998,325; (b) M. Kitamura, S. Zaman, K. Narasaka, Synlett 2001,974-976; (c) S. M. Zaman, K. Kitamura,K.Narasaka,Bull.Chem.Soc.Jpn.2003,76,1055-1062.
[14](a)Boivin,J.;Schiano,A.-M.;Zard,S.Z.;Zhang,H.Tetrahedron Lett.1999,40, 4531-4534;(b)Narasaka K.;Kitamura,M.Eur.J.Org.Chem.2005,4505-4519.
[15](a)Ullmann,F.Ber.Dtsch.Chem.Ges.1903,36,2382;(b)Goldberg,I.Ber. Dtsch.Chem.Ges.1906,39,1691-1692.
[16](a)Krause,N.Modern Organocopper Chemistry; Wiley-VCH: Weinheim, Germany,2002;(b)Ley,S.V.;Thomas,A.W.Angew. Chem.,Int.Ed.2003,42, 5400-5449.(c)Monnier,F.;Taillefer,M.Angew.Chem.,Int.Ed.2009,48, 6954-6971.(d)Hassan,J.;Sevignon,M.;Gozzi,C.;Schulz,E.;Lemaire,M. Chem.Rev.2002,102,1359-1469.(e)Chemler,S.R.;Fuller,P.H.Chem.Soc. Rev.2007,36,1153-1160.(f)Beletskaya,I.P.;Cheprakov,A.V Coord.Chem. Rev.2004,248,2337-2364.(g)Finet,J.-P.;Fedorov,A.Y;Combes,S.;Boyer,G Curr.Org.Chem.2002,6,597-626.(h)Sperotto,E.;van Klink,G.P.M.;van Koten,G.;de Vries,J.G Dalton Trans.2010,39,10338-10351.(i)Evano,G.; B1anchard,N.;Toumi,M.Chem.Rev.2008,108,3054-3131.
[17](a)Jones,G. O.;Liu,P.;Houk,K.N.;Buchwald,S.L.J.Am.Chem.Soc.2010, J32,6205-6213.(d)Strieter,E.R.;Bhayana,B.;Buchwald,S.L.J.Am.Chem. Soc.2009,131,78-88.(e)Strieter,E.R.;Blackmond,D.G.;Buchwald,S.L.J. Am.Chem.Soc.2005,127,4120-4121;(g)Tye,J.W.;Weng,Z.;Johns,A.M.; Incarvito,C.D.;Hartwig,J.F.J.Am.Chem.Soc.2008,130,9971-9983;(i)Franc, G;Cacciuttolo,Q.;Lefevre,G.;Adamo,C.;Ciofini,I.;Jutand,A.ChemCatChem 2011,3,305-309;(m)Yu,H.-Z.;Jiang,Y-Y;Fu,Y.;Liu,L.,J.Am.Chem.Soc. 2010,132,18078-18091;(o)Zhang,S.-L.;Liu,L.;Fu,Y;Guo,Q.-X. Organometallics 2007,26,4546-4554;
[18](a)Paine,A.J.J.Am.Chem.Soc.1987,109,1496-1502;(b)Mansour,M.; Giacovazzi,R.;Ouali,A.;Taillefer,M.;Jutand,A.Chem.Commun.2008, 6051-6053;(c)Franc,G.;Jutand,A.Dalton Trans.2010,39,7873-7875;(d) Huang,Z.;Hartwig,J.F.Angew.Chem.,Int.Ed.2012,51,1028-1032;(e)He,C.; Zhang,G.;Ke,J.;Zhang,H.;Miller,J.T.;Kropf, A.J.;Lei,A.J.Am.Chem.Soc. 2013 135,488-493
[19](a)Wang,W.;Li,J.;Wang,K.;Smirnova,T.I.;Oldfield,E.J.Am.Chem.Soc. 2011,133,6525.(b)Henry,G. D.Tetrahedron 2004,60,6043.(d)Michael,J.P. Nat. Prod. Rep.2005,22,627.(c)Carey,J.S.;Laffan,D.;Thomson,C.;Williams, M.T.Org.Binomol.Chem.2006,4,2337.
[20](a)Heller,B.;Hapke,M.Chem.Soc.Rev.2007,36,1085.(b)Wang,Y.-F.;Chiba, S.J. Am. Chem. Soc.2009,131,12570. (c) Movassaghi, M.; Hill, M. D.; Ahmad, O. K. J. Am. Chem. Soc.2007,129,10096. (d) Yoshida, K.; Kawagoe, F.; Hayashi, K.; Horiuchi, S.; Imamoto, T.; Yanagisawa, A. Org. Lett.2009,11,515. (e) De Paolis, O.; Baffoe, J.; Landge, S. M.; T€or€ok, B. Synthesis 2008,3423.
[21]Guan, Z.-H.; Zhang, Z.-Y; Ren, Z.-H.; Wang, Y.-Y.; Zhang, X. J. Org. Chem. 2011,76,339.
[22](a) Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc.2002,124,2528. (b) Nitta, M.; Iino, Y Bull. Chem. Soc. Jpn.1986,59,2365. (c) Deeming, A. J.; Owen, D. W.; Powell, N. I. J. Organomet. Chem.1990,398,299.
[23]Takai, K.; Katsura, N.; Kunisada, Y. Chem. Commun.2001,1724.
[24]Liu, S.; Liebeskind, L. S.J. Am. Chem. Soc.2008,130,6918.