过渡金属催化的基于季铵盐C—N键断裂的偶联反应研究进展
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摘要
含有碳-氮(C—N)键的胺类化合物广泛存在于天然产物、药物分子和功能材料之中.C—N键作为分布最广且相对惰性的化学键之一,通过对其选择性的断裂来构建新的碳-碳(C—C)或碳-杂(C—X)键在近年来逐渐发展为一种新的合成方法.季铵盐化合物易于从胺类化合物合成,发生C—N键断裂相对容易.综述了近年来以季铵盐为原料通过过渡金属催化的C—N键断裂实现的交叉偶联反应.
Amines containing carbon-nitrogen(C—N) bonds are widely distributed in natural products, drug molecules and functional materials. C—N bonds are one of the most abundant and inert bonds in organic molecules. Selective cleavage of C—N bonds to construct carbon-carbon(C—C) and carbon-heteroatom(C—X) bonds represents a new synthetic method in organic synthesis. It is difficult for the direct cleavage of C—N bond. Ammonium salts are a series of stable compounds easily obtained from amines. The recent progress of transition-metal-catalyzed cross-coupling reactions via C—N bond cleavage using ammonium salts as starting materials is summerized.
Amines containing carbon-nitrogen(C—N) bonds are widely distributed in natural products, drug molecules and functional materials. C—N bonds are one of the most abundant and inert bonds in organic molecules. Selective cleavage of C—N bonds to construct carbon-carbon(C—C) and carbon-heteroatom(C—X) bonds represents a new synthetic method in organic synthesis. It is difficult for the direct cleavage of C—N bond. Ammonium salts are a series of stable compounds easily obtained from amines. The recent progress of transition-metal-catalyzed cross-coupling reactions via C—N bond cleavage using ammonium salts as starting materials is summerized.
引文
[1](a)Paul,F.;Patt,J.;Hartwig,J.F.J.Am.Chem.Soc.1994,116,5969.(b)Guram,A.S.;Buchwald,S.L.J.Am.Chem.Soc.1994,116,7901.(c)Muci,A.R.;Buchwald,S.L.Top.Curr.Chem.2002,219,131.(d)Hartwig,J.F.Acc.Chem.Res.2008,41,1534.
[2](a)Blanksby,S.J.;Ellison,G.B.Acc.Chem.Res.2003,36,255.(b)Yao,X.-Q.;Hou,X.-J.;Jiao,H.;Xiang,H.-W.;Li,Y.-W.J.Phys.Chem.A 2003,107,9991.
[3](a)Bonanno,J.B.;Henry,T.P.;Neithamer,D.R.;Wolczanski,P.T.;Lobkovsky,E.B.J.Am.Chem.Soc.1996,118,5132.(b)Ueno,S.;Chatani,N.;Kakiuchi,F.J.Am.Chem.Soc.2007,129,6098.(c)Koreeda,T.;Kochi,T.;Kakiuchi,F.J.Am.Chem.Soc.2009,131,7238.(d)Tobisu,M.;Nakamura,K.;Chatani,N.J.Am.Chem.Soc.2014,136,5587.(e)Zhao,Y.;Snieckus,V.Org.Lett.2014,16,3200.(f)Cong,X.;Fan,F.;Ma,P.;Luo,M.;Chen,H.;Zeng,X.J.Am.Chem.Soc.2017,139,15182.
[4](a)Geng,W.;Zhang,W.-X.;Hao,W.;Xi,Z.J.Am.Chem.Soc.2012,134,20230.(b)Xie,Y.;Hu,J.;Wang,Y.;Xia,C.;Huang,H.J.Am.Chem.Soc.2012,134,20613.(c)Hao,W.;Geng,W.;Zhang,W.X.;Xi,Z.Chem.-Eur.J.2014,20,2605.
[5]Balz,G.;Schiemann,G.Ber.-Umweltbundesamt(Ger.)1927,60B,1186.
[6]Brasen,W.R.;Hauser,C.R.Org.Synth.1954,34,58.
[7](a)Ouyang,K.;Hao,W.;Zhang,W.-X.;Xi,Z.Chem.Rev.2015,115,12045.(b)Wang,Q.;Su,Y.;Li,L.;Huang,H.Chem.Soc.Rev.2016,45,1257.(c)Dander,J.E.;Garg,N.K.ACS Catal.2017,7,1413.(d)Takise,R.;Muto,K.;Yamaguchi,J.Chem.Soc.Rev.2017,46,5864.(e)Gao,Y.;Ji,C.-L.;Hong,X.Sci.China:Chem.2017,60,1413.(f)Liu,J.;Yuan,S.;Song,X.;Qiu,G.Chin.J.Org.Chem.2016,1790.(g)Tang,H.;Huo,X.;Meng,Q.;Zhang,W.Acta Chim.Sinica2016,74,219(in Chinese).(汤淏溟,霍小红,孟庆华,张万斌,化学学报,2016,74,219.)(h)Zeng,M.;Song,C.;Cui,D.Chin.J.Org.Chem.2017,37,1352(in Chinese)(曾明,宋婵,崔冬梅,有机化学,2017,37,1352.)
[8](a)Eds.:de Meijere,A.;Diederich,F.;Metal-Catalyzed CrossCoupling Reactions,Wiley-VCH,Weinheim,2004,p.437.(b)Eds.:de Meijere,A.;Braese,S.;Oestreich,M.Metal-Catalyzed Cross-Coupling Reactions And More,Wiley-VCH,Weinheim,2014.
[9]Corriu,R.J.P.;Masse,J.P.J.Chem.Soc.,Chem.Commun.1972,144a.
[10]Tamao,K.;Sumitani,K.;Kumada,M.J.Am.Chem.Soc.1972,94,4374.
[11]Terao,J.;Kambe,N.Acc.Chem.Res.2008,41,1545.
[12]Wenkert,E.;Han,A.-L.;Jenny,C.-J.J.Chem.Soc.,Chem.Commun.1988,975.
[13](a)Wenkert,E.;Michelotti,E.L.;Swindell,C.S.J.Am.Chem.Soc.1979,101,2246.(b)Yu,D.-G.;Li,B.-J.;Shi,Z.-J.Acc.Chem.Res.2010,43,1486.(c)Rosen,B.M.;Quasdorf,K.W.;Wilson,D.A.;Zhang,N.;Resmerita,A.-M.;Garg,N.K.;Percec,V.Chem.Rev.2011,111,1346.(d)Su,B.;Cao,Z.-C.;Shi,Z.-J.Acc.Chem.Res.2015,48,886.(e)Tobisu,M.;Chatani,N.Acc.Chem.Res.2015,48,1717.
[14](a)Clot,E.;Eisenstein,O.;Jasim,N.;Mac Gregor,S.A.;Mc Grady,J.E.;Perutz,R.N.Acc.Chem.Res.2011,44,333.(b)Keyes,L.;Love,J.A.RSC Catal.Ser.2013,11,159.(c)Yang,S.-D.In Homogeneous Transition-Metal-Catalyzed C—F Sctivation,John Wiley&Sons,New York,2015,pp.203~268.
[15]Reeves,J.T.;Fandrick,D.R.;Tan,Z.;Song,J.J.;Lee,H.;Yee,N.K.;Senanayake,C.H.Org.Lett.2010,12,4388.
[16]Guo,W.-J.;Wang,Z.-X.Tetrahedron 2013,69,9580.
[17]Guisan-Ceinos,M.;Martin-Heras,V.;Tortosa,M.J.Am.Chem.Soc.2017,139,8448.
[18]Ma,S.;Liu,Q.;Tang,X.;Cai,Y.Asian J.Org.Chem.2017,6,1209.
[19](a)Dieck,H.A.;Heck,R.F.J.Am.Chem.Soc.1974,96,1133.(b)Heck,R.F.Acc.Chem.Res.1979,12,146.
[20]Pan,Y.;Zhang,Z.;Hu,H.Synthesis 1995,245.
[21](a)Miyaura,N.;Suzuki,A.Chem.Rev.1995,95,2457.(b)Miyaura,N.Top.Curr.Chem.2002,219,11.
[22]Blakey,S.B.;Mac Millan,D.W.C.J.Am.Chem.Soc.2003,125,6046.
[23]Buszek,K.R.;Brown,N.Org.Lett.2007,9,707.
[24]de la Herrán,G.;Segura,A.;Csák?,A.G.Org.Lett.2007,9,961.
[25]Humphrey,G.R.;Kuethe,J.T.Chem.Rev.2006,106,2875.
[26]Maity,P.;Shacklady-Mc Atee,D.M.;Yap,G.P.A.;Sirianni,E.R.;Watson,M.P.J.Am.Chem.Soc.2013,135,280.
[27]Shacklady-Mc Atee,D.M.;Roberts,K.M.;Basch,C.H.;Song,Y.G.;Watson,M.P.Tetrahedron 2014,70,4257.
[28]Liu,X.-Y.;Zhu,H.-B.;Shen,Y.-J.;Jiang,J.;Tu,T.Chin.Chem.Lett.2017,28,350.
[29]Wang,T.;Yang,S.;Xu,S.;Han,C.;Guo,G.;Zhao,J.RSC Adv.2017,7,15805.
[30]Turtscher,P.L.;Davis,H.J.;Phipps,R.J.Synthesis 2018,50,793.
[31]Basch,C.H.;Liao,J.;Xu,J.;Piane,J.J.;Watson,M.P.J.Am.Chem.Soc.2017,139,5313.
[32](a)Katritzky,A.R.;Gruntz,U.;Kenny,D.H.;Rezende,M.C.;Sheikh,H.J.Chem.Soc.,Perkin Trans.1 1979,430.(b)Katritzky,A.R.;Marson,C.M.Angew.Chem.,Int.Ed.1984,23,420.
[33](a)Shao,Z.;Li,X.;Chang,H.;Wei,W.Chemistry 2013,76,704.(b)Dilman,A.D.;Levin,V.V.Tetrahedron Lett.2016,57,3986.
[34]Xie,L.G.;Wang,Z.X.Angew.Chem.,Int.Ed.2011,50,4901.
[35](a)Zhang,X.-Q.;Wang,Z.-X.J.Org.Chem.2012,77,3658.(b)Yang,X.;Wang,Z.-X.Organometallics 2014,33,5863.
[36]Wang,D.-Y.;Morimoto,K.;Yang,Z.-K.;Wang,C.;Uchiyama,M.Chem.-Asian J.2017,12,2554.
[37](a)Stille,J.K.Angew.Chem.,Int.Ed.1986,25,508.(b)Fugami,K.;Kosugi,M.Top.Curr.Chem.2002,219,87.
[38]Wang,D.-Y.;Kawahata,M.;Yang,Z.-K.;Miyamoto,K.;Komagawa,S.;Yamaguchi,K.;Wang,C.;Uchiyama,M.Nat.Commun.2016,7,12937.
[39]Yamamura,M.;Moritani,I.;Murahashi,S.-I.J.Organomet.Chem.1975,91,C39.(b)Murahashi,S.;Yamamura,M.;Yanagisawa,K.;Mita,N.;Kondo,K.J.Org.Chem.1979,44,2408.(c)Giannerini,M.;Fa?anás-Mastral,M.;Feringa,B.L.Nat.Chem.2013,5,667.
[40]Yang,Z.-K.;Wang,D.-Y.;Minami,H.;Ogawa,H.;Ozaki,T.;Saito,T.;Miyamoto,K.;Wang,C.;Uchiyama,M.Chem.-Eur.J.2016,22,15693.
[41]He,F.;Wang,Z.-X.Tetrahedron 2017,73,4450.
[42]Ogawa,H.;Yang,Z.-K.;Minami,H.;Kojima,K.;Saito,T.;Wang,C.;Uchiyama,M.ACS Catal.2017,7,3988.
[43]Zhu,F.;Tao,J.-L.;Wang,Z.-X.Org.Lett.2015,17,4926.
[44]Yu,S.;Liu,S.;Lan,Y.;Wan,B.;Li,X.J.Am.Chem.Soc.2015,137,1623.
[45]Uemura,T.;Yamaguchi,M.;Chatani,N.Angew.Chem.,Int.Ed.2016,55,3162.
[46]Klauck,F.J.R.;James,M.J.;Glorius,F.Angew.Chem.,Int.Ed.2017,56,12336.
[47]Spettel,M.;Pollice,R.;Schnürch,M.Org.Lett.2017,19,4287.
[48](a)Hofmann,A.W.Justus Liebigs Ann.Chem.1851,79,11.(b)von Hofmann,A.W.Justus Liebigs Ann.Chem.1851,78,253.
[49]Li,J.W.;Zheng,Z.J.;Xiao,T.T.;Xu,P.F.;Wei,H.Asian J.Org.Chem.2018,7,133.
[50](a)Gambarotta,S.;Alper,H.J.Organomet.Chem.1980,194,C19.(b)Lei,Y.;Zhang,R.;Wu,Q.;Mei,H.;Xiao,B.;Li,G.J.Mol.Catal.A 2014,381,120.(c)Lei,Y.;Zhang,R.;Wu,L.;Wu,Q.;Mei,H.;Li,G.Appl.Organomet.Chem.2014,28,310.
[51]Moragas,T.;Gaydou,M.;Martin,R.Angew.Chem.,Int.Ed.2016,55,5053.
[52]Zhang,X.-Q.;Wang,Z.-X.Org.Bioorg.Chem.2014,12,1448.
[53]Zhang,H.;Hagihara,S.;Itami,K.Chem.-Eur.J.2015,21,16796.
[54]Hu,J.;Sun,H.;Cai,W.;Pu,X.;Zhang,Y.;Shi,Z.J.Org.Chem.2016,81,14.
[55]Basch,C.H.;Cobb,K.M.;Watson,M.P.Org.Lett.2016,18,136.
[56]Mfuh,A.M.;Doyle,J.D.;Chhetri,B.;Arman,H.D.;Larionov,O.V.J.Am.Chem.Soc.2016,138,2985.
[57](a)Said,S.A.;Fiksdahl,A.Tetrahedron:Asymmetry 2001,12,1947.(b)Gui,Y.;Tian,S.K.Org.Lett.2017,19,1554.(c)Erika,B.;Istvan,G.;Gyorgy,K.Lett.Org.Chem.2011,8,22.
[58]Lu,F.L.;Chen,Z.Y.;Li,Z.;Wang,X.Y.;Peng,X.Y.;Li,C.;Li,R.;Pei,H.Q.;Wang,H.M.;Gao,M.Asian J.Org.Chem.2018,7,141.
[2](a)Blanksby,S.J.;Ellison,G.B.Acc.Chem.Res.2003,36,255.(b)Yao,X.-Q.;Hou,X.-J.;Jiao,H.;Xiang,H.-W.;Li,Y.-W.J.Phys.Chem.A 2003,107,9991.
[3](a)Bonanno,J.B.;Henry,T.P.;Neithamer,D.R.;Wolczanski,P.T.;Lobkovsky,E.B.J.Am.Chem.Soc.1996,118,5132.(b)Ueno,S.;Chatani,N.;Kakiuchi,F.J.Am.Chem.Soc.2007,129,6098.(c)Koreeda,T.;Kochi,T.;Kakiuchi,F.J.Am.Chem.Soc.2009,131,7238.(d)Tobisu,M.;Nakamura,K.;Chatani,N.J.Am.Chem.Soc.2014,136,5587.(e)Zhao,Y.;Snieckus,V.Org.Lett.2014,16,3200.(f)Cong,X.;Fan,F.;Ma,P.;Luo,M.;Chen,H.;Zeng,X.J.Am.Chem.Soc.2017,139,15182.
[4](a)Geng,W.;Zhang,W.-X.;Hao,W.;Xi,Z.J.Am.Chem.Soc.2012,134,20230.(b)Xie,Y.;Hu,J.;Wang,Y.;Xia,C.;Huang,H.J.Am.Chem.Soc.2012,134,20613.(c)Hao,W.;Geng,W.;Zhang,W.X.;Xi,Z.Chem.-Eur.J.2014,20,2605.
[5]Balz,G.;Schiemann,G.Ber.-Umweltbundesamt(Ger.)1927,60B,1186.
[6]Brasen,W.R.;Hauser,C.R.Org.Synth.1954,34,58.
[7](a)Ouyang,K.;Hao,W.;Zhang,W.-X.;Xi,Z.Chem.Rev.2015,115,12045.(b)Wang,Q.;Su,Y.;Li,L.;Huang,H.Chem.Soc.Rev.2016,45,1257.(c)Dander,J.E.;Garg,N.K.ACS Catal.2017,7,1413.(d)Takise,R.;Muto,K.;Yamaguchi,J.Chem.Soc.Rev.2017,46,5864.(e)Gao,Y.;Ji,C.-L.;Hong,X.Sci.China:Chem.2017,60,1413.(f)Liu,J.;Yuan,S.;Song,X.;Qiu,G.Chin.J.Org.Chem.2016,1790.(g)Tang,H.;Huo,X.;Meng,Q.;Zhang,W.Acta Chim.Sinica2016,74,219(in Chinese).(汤淏溟,霍小红,孟庆华,张万斌,化学学报,2016,74,219.)(h)Zeng,M.;Song,C.;Cui,D.Chin.J.Org.Chem.2017,37,1352(in Chinese)(曾明,宋婵,崔冬梅,有机化学,2017,37,1352.)
[8](a)Eds.:de Meijere,A.;Diederich,F.;Metal-Catalyzed CrossCoupling Reactions,Wiley-VCH,Weinheim,2004,p.437.(b)Eds.:de Meijere,A.;Braese,S.;Oestreich,M.Metal-Catalyzed Cross-Coupling Reactions And More,Wiley-VCH,Weinheim,2014.
[9]Corriu,R.J.P.;Masse,J.P.J.Chem.Soc.,Chem.Commun.1972,144a.
[10]Tamao,K.;Sumitani,K.;Kumada,M.J.Am.Chem.Soc.1972,94,4374.
[11]Terao,J.;Kambe,N.Acc.Chem.Res.2008,41,1545.
[12]Wenkert,E.;Han,A.-L.;Jenny,C.-J.J.Chem.Soc.,Chem.Commun.1988,975.
[13](a)Wenkert,E.;Michelotti,E.L.;Swindell,C.S.J.Am.Chem.Soc.1979,101,2246.(b)Yu,D.-G.;Li,B.-J.;Shi,Z.-J.Acc.Chem.Res.2010,43,1486.(c)Rosen,B.M.;Quasdorf,K.W.;Wilson,D.A.;Zhang,N.;Resmerita,A.-M.;Garg,N.K.;Percec,V.Chem.Rev.2011,111,1346.(d)Su,B.;Cao,Z.-C.;Shi,Z.-J.Acc.Chem.Res.2015,48,886.(e)Tobisu,M.;Chatani,N.Acc.Chem.Res.2015,48,1717.
[14](a)Clot,E.;Eisenstein,O.;Jasim,N.;Mac Gregor,S.A.;Mc Grady,J.E.;Perutz,R.N.Acc.Chem.Res.2011,44,333.(b)Keyes,L.;Love,J.A.RSC Catal.Ser.2013,11,159.(c)Yang,S.-D.In Homogeneous Transition-Metal-Catalyzed C—F Sctivation,John Wiley&Sons,New York,2015,pp.203~268.
[15]Reeves,J.T.;Fandrick,D.R.;Tan,Z.;Song,J.J.;Lee,H.;Yee,N.K.;Senanayake,C.H.Org.Lett.2010,12,4388.
[16]Guo,W.-J.;Wang,Z.-X.Tetrahedron 2013,69,9580.
[17]Guisan-Ceinos,M.;Martin-Heras,V.;Tortosa,M.J.Am.Chem.Soc.2017,139,8448.
[18]Ma,S.;Liu,Q.;Tang,X.;Cai,Y.Asian J.Org.Chem.2017,6,1209.
[19](a)Dieck,H.A.;Heck,R.F.J.Am.Chem.Soc.1974,96,1133.(b)Heck,R.F.Acc.Chem.Res.1979,12,146.
[20]Pan,Y.;Zhang,Z.;Hu,H.Synthesis 1995,245.
[21](a)Miyaura,N.;Suzuki,A.Chem.Rev.1995,95,2457.(b)Miyaura,N.Top.Curr.Chem.2002,219,11.
[22]Blakey,S.B.;Mac Millan,D.W.C.J.Am.Chem.Soc.2003,125,6046.
[23]Buszek,K.R.;Brown,N.Org.Lett.2007,9,707.
[24]de la Herrán,G.;Segura,A.;Csák?,A.G.Org.Lett.2007,9,961.
[25]Humphrey,G.R.;Kuethe,J.T.Chem.Rev.2006,106,2875.
[26]Maity,P.;Shacklady-Mc Atee,D.M.;Yap,G.P.A.;Sirianni,E.R.;Watson,M.P.J.Am.Chem.Soc.2013,135,280.
[27]Shacklady-Mc Atee,D.M.;Roberts,K.M.;Basch,C.H.;Song,Y.G.;Watson,M.P.Tetrahedron 2014,70,4257.
[28]Liu,X.-Y.;Zhu,H.-B.;Shen,Y.-J.;Jiang,J.;Tu,T.Chin.Chem.Lett.2017,28,350.
[29]Wang,T.;Yang,S.;Xu,S.;Han,C.;Guo,G.;Zhao,J.RSC Adv.2017,7,15805.
[30]Turtscher,P.L.;Davis,H.J.;Phipps,R.J.Synthesis 2018,50,793.
[31]Basch,C.H.;Liao,J.;Xu,J.;Piane,J.J.;Watson,M.P.J.Am.Chem.Soc.2017,139,5313.
[32](a)Katritzky,A.R.;Gruntz,U.;Kenny,D.H.;Rezende,M.C.;Sheikh,H.J.Chem.Soc.,Perkin Trans.1 1979,430.(b)Katritzky,A.R.;Marson,C.M.Angew.Chem.,Int.Ed.1984,23,420.
[33](a)Shao,Z.;Li,X.;Chang,H.;Wei,W.Chemistry 2013,76,704.(b)Dilman,A.D.;Levin,V.V.Tetrahedron Lett.2016,57,3986.
[34]Xie,L.G.;Wang,Z.X.Angew.Chem.,Int.Ed.2011,50,4901.
[35](a)Zhang,X.-Q.;Wang,Z.-X.J.Org.Chem.2012,77,3658.(b)Yang,X.;Wang,Z.-X.Organometallics 2014,33,5863.
[36]Wang,D.-Y.;Morimoto,K.;Yang,Z.-K.;Wang,C.;Uchiyama,M.Chem.-Asian J.2017,12,2554.
[37](a)Stille,J.K.Angew.Chem.,Int.Ed.1986,25,508.(b)Fugami,K.;Kosugi,M.Top.Curr.Chem.2002,219,87.
[38]Wang,D.-Y.;Kawahata,M.;Yang,Z.-K.;Miyamoto,K.;Komagawa,S.;Yamaguchi,K.;Wang,C.;Uchiyama,M.Nat.Commun.2016,7,12937.
[39]Yamamura,M.;Moritani,I.;Murahashi,S.-I.J.Organomet.Chem.1975,91,C39.(b)Murahashi,S.;Yamamura,M.;Yanagisawa,K.;Mita,N.;Kondo,K.J.Org.Chem.1979,44,2408.(c)Giannerini,M.;Fa?anás-Mastral,M.;Feringa,B.L.Nat.Chem.2013,5,667.
[40]Yang,Z.-K.;Wang,D.-Y.;Minami,H.;Ogawa,H.;Ozaki,T.;Saito,T.;Miyamoto,K.;Wang,C.;Uchiyama,M.Chem.-Eur.J.2016,22,15693.
[41]He,F.;Wang,Z.-X.Tetrahedron 2017,73,4450.
[42]Ogawa,H.;Yang,Z.-K.;Minami,H.;Kojima,K.;Saito,T.;Wang,C.;Uchiyama,M.ACS Catal.2017,7,3988.
[43]Zhu,F.;Tao,J.-L.;Wang,Z.-X.Org.Lett.2015,17,4926.
[44]Yu,S.;Liu,S.;Lan,Y.;Wan,B.;Li,X.J.Am.Chem.Soc.2015,137,1623.
[45]Uemura,T.;Yamaguchi,M.;Chatani,N.Angew.Chem.,Int.Ed.2016,55,3162.
[46]Klauck,F.J.R.;James,M.J.;Glorius,F.Angew.Chem.,Int.Ed.2017,56,12336.
[47]Spettel,M.;Pollice,R.;Schnürch,M.Org.Lett.2017,19,4287.
[48](a)Hofmann,A.W.Justus Liebigs Ann.Chem.1851,79,11.(b)von Hofmann,A.W.Justus Liebigs Ann.Chem.1851,78,253.
[49]Li,J.W.;Zheng,Z.J.;Xiao,T.T.;Xu,P.F.;Wei,H.Asian J.Org.Chem.2018,7,133.
[50](a)Gambarotta,S.;Alper,H.J.Organomet.Chem.1980,194,C19.(b)Lei,Y.;Zhang,R.;Wu,Q.;Mei,H.;Xiao,B.;Li,G.J.Mol.Catal.A 2014,381,120.(c)Lei,Y.;Zhang,R.;Wu,L.;Wu,Q.;Mei,H.;Li,G.Appl.Organomet.Chem.2014,28,310.
[51]Moragas,T.;Gaydou,M.;Martin,R.Angew.Chem.,Int.Ed.2016,55,5053.
[52]Zhang,X.-Q.;Wang,Z.-X.Org.Bioorg.Chem.2014,12,1448.
[53]Zhang,H.;Hagihara,S.;Itami,K.Chem.-Eur.J.2015,21,16796.
[54]Hu,J.;Sun,H.;Cai,W.;Pu,X.;Zhang,Y.;Shi,Z.J.Org.Chem.2016,81,14.
[55]Basch,C.H.;Cobb,K.M.;Watson,M.P.Org.Lett.2016,18,136.
[56]Mfuh,A.M.;Doyle,J.D.;Chhetri,B.;Arman,H.D.;Larionov,O.V.J.Am.Chem.Soc.2016,138,2985.
[57](a)Said,S.A.;Fiksdahl,A.Tetrahedron:Asymmetry 2001,12,1947.(b)Gui,Y.;Tian,S.K.Org.Lett.2017,19,1554.(c)Erika,B.;Istvan,G.;Gyorgy,K.Lett.Org.Chem.2011,8,22.
[58]Lu,F.L.;Chen,Z.Y.;Li,Z.;Wang,X.Y.;Peng,X.Y.;Li,C.;Li,R.;Pei,H.Q.;Wang,H.M.;Gao,M.Asian J.Org.Chem.2018,7,141.