过渡金属催化的sp~3碳氢键活化及酰胺与羧酸甲基化反应
|
摘要
过去二十年来,过渡金属催化的碳氢键活化反应已经被广泛应用于芳烃和杂环芳烃的官能团化反应。相较于sp2碳氢键活化反应的研究,过渡金属催化的sp3碳氢键活化反应的研究相对较少。这是由于sp3碳氢键没有空的低能量轨道和填充的高能量轨道,所以不能与金属原子的轨道相互作用。因此,催化活化sp3碳氢键具有更大的挑战性。
本论文报道了不同的sp3碳氢键活化来实现唑类化合物的N-烷基化反应以及铜催化酰胺与羧酸甲基化反应。论文主要分为三部分：
1.铁催化下咪唑与苄基化合物直接偶联以构筑碳氮键。便宜的FeCl2/DTBPP催化剂体系对于咪唑N-烷基化更加有实用,且相比较传统的咪唑N-烷基化方法,苄基化合物更加易得和环境友好。
2.铁催化下咪唑与酰胺化合物直接偶联以构筑碳氮键。酰胺和磺酰胺中氮邻位的sp3碳氢键和唑类化合物中氮氢键在FeCl2/DTBP催化下可以顺利发生氧化偶联反应。一系列范围很广的酰胺和磺酰胺都能很好的适用于这个反应。
3.铜催化下酰胺的N-甲基化和羧酸的O-甲基化反应,反应以有机过氧化物作为甲基的来源。各种酰胺和羧酸在该反应条件下被甲基化以合成N-甲基酰胺和酯。初步的机理研究表明该反应经过一个自由基的过程。
Transition metal-catalyzed C-H bonds activation methods have been widely developed for the functionalization of arenes and heteroarenes in the past two decades. Compared to sp2C-H activation, much less research has been devoted to the activation of more inert sp3C-H bonds. The sp3C-H bonds have no empty lowenergy orbitals or filled high-energy orbitals that could readily interact with orbitals of the metal center, as is the case with unsaturated hydrocarbons. Therefore, catalytic sp3C-H bonds activation seems to represent a significantly bigger challenge.
In this paper,we report N-Alkylation of azoles via oxidative activation of C-H bonds and N-methylation of amides and O-methylation of carboxylic acids.
1. Iron-catalyzed direct C-N bond formation between imidazoles and benzylic hydrocarbons is described. The inexpensive and readily available catalyst oxidant system is of practical interest for N-alkylation of imidazoles. Compared to traditional N-alkylation of imidazoles, benzylic hydrocarbons are more easily available and environmentally friendly than alkyl halides.
2. Iron-catalyzed direct C-N bond formation between azoles and amides is described. The oxidative coupling reactions of sp3C-H bonds adjacent to a nitrogen atom in amides and sulfonamides with the N-H bond in azoles proceeded smoothly in the presence of FeCl2and di-tert-butyl peroxide (DTBP). A wide range of amides and sulfonamides can be used as substrate for N-alkylation of azoles.
3. The copper-catalyzed N-methylation of amides and O-methylation of carboxylic acids by using peroxides as the methylating reagent are described. Various amides and carboxylic acids were methylated affording N-substituted amides and esters. Tentative mechanistic studies suggest that this reaction is likely to involve a radical process.
本论文报道了不同的sp3碳氢键活化来实现唑类化合物的N-烷基化反应以及铜催化酰胺与羧酸甲基化反应。论文主要分为三部分：
1.铁催化下咪唑与苄基化合物直接偶联以构筑碳氮键。便宜的FeCl2/DTBPP催化剂体系对于咪唑N-烷基化更加有实用,且相比较传统的咪唑N-烷基化方法,苄基化合物更加易得和环境友好。
2.铁催化下咪唑与酰胺化合物直接偶联以构筑碳氮键。酰胺和磺酰胺中氮邻位的sp3碳氢键和唑类化合物中氮氢键在FeCl2/DTBP催化下可以顺利发生氧化偶联反应。一系列范围很广的酰胺和磺酰胺都能很好的适用于这个反应。
3.铜催化下酰胺的N-甲基化和羧酸的O-甲基化反应,反应以有机过氧化物作为甲基的来源。各种酰胺和羧酸在该反应条件下被甲基化以合成N-甲基酰胺和酯。初步的机理研究表明该反应经过一个自由基的过程。
Transition metal-catalyzed C-H bonds activation methods have been widely developed for the functionalization of arenes and heteroarenes in the past two decades. Compared to sp2C-H activation, much less research has been devoted to the activation of more inert sp3C-H bonds. The sp3C-H bonds have no empty lowenergy orbitals or filled high-energy orbitals that could readily interact with orbitals of the metal center, as is the case with unsaturated hydrocarbons. Therefore, catalytic sp3C-H bonds activation seems to represent a significantly bigger challenge.
In this paper,we report N-Alkylation of azoles via oxidative activation of C-H bonds and N-methylation of amides and O-methylation of carboxylic acids.
1. Iron-catalyzed direct C-N bond formation between imidazoles and benzylic hydrocarbons is described. The inexpensive and readily available catalyst oxidant system is of practical interest for N-alkylation of imidazoles. Compared to traditional N-alkylation of imidazoles, benzylic hydrocarbons are more easily available and environmentally friendly than alkyl halides.
2. Iron-catalyzed direct C-N bond formation between azoles and amides is described. The oxidative coupling reactions of sp3C-H bonds adjacent to a nitrogen atom in amides and sulfonamides with the N-H bond in azoles proceeded smoothly in the presence of FeCl2and di-tert-butyl peroxide (DTBP). A wide range of amides and sulfonamides can be used as substrate for N-alkylation of azoles.
3. The copper-catalyzed N-methylation of amides and O-methylation of carboxylic acids by using peroxides as the methylating reagent are described. Various amides and carboxylic acids were methylated affording N-substituted amides and esters. Tentative mechanistic studies suggest that this reaction is likely to involve a radical process.
引文
(1)Dick, A. R.; Sanford, M. S. Tetrahedron 2006,62,2439.
(2)a) Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev.2003,103,2861; b) Miiller, P.; Fruit, C. Chem. Rev.2003,103,2905; c) Davies, H. M. L.; Manning, J. R. Nature 2008, 451,417.
(3)Boutadla, Y.; Davies, D. L.; Macgregor, S. A.; Poblador-Bahamonde, A. I. Dalton Trans.2009,5820.
(4)a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev.2007,107,174; b) Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed.2009,48,9792; c) Le Bras, J.; Muzart, J. Chem. Rev.2011,111,1170.
(5)a) Diaz-Requejo, M. M.; Perez, P. J. Chem. Rev.2008,108,3379; b) Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev.2009,38,3242; c) Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem. Eur. J.2010,16,2654; d) Baudoin, O. Chem. Soc. Rev.2011,40,4902; e) Ramirez, T. A.; Zhao, B.; Shi, Y. Chem. Soc. Rev.2012,41,931; f) Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed.2013,52,
11726.
(6)a) Li, C. J. Acc. Chem. Res.2009,42,335; b) Yoo, W. J.; Li, C. J. Top. Curr. Chem. 2010,292,281; c) Scheuermann, C. J. Chem. Eur. J.2010,5,436; d) Ashenhurst, J. A. Chem. Soc. Rev.2010,39,540; e) Yeung, C. S.; Dong, V. M. Chem. Rev.2011, 111,1215; f) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev.2011,40,5068; g) Jones, K. M.; Klussmann, M. Synlett 2012,23,159. (7) Li, Z.; Li, C.-J.J. Am. Chem. Soc.2005,128,56.
(8)Li, Z.; Cao, L.; Li, C.-J. Angew. Chem., Int. Ed.2007,46,6505.
(9)Correia, C. A.; Li, C.-J. Tetrahedron Lett.2010,51,1172.
(10)Borduas, N.; Powell, D. A. J. Org. Chem.2008,73,7822.
(11)Cheng, D.; Bao, W. Adv. Synth. Catal.2008,350,1263.
(12)Pinter, A.; Sud, A.; Sureshkumar, D.; Klussmann, M. Angew. Chem., Int. Ed.2010, 49,5004.
(13)Li, Y.-Z.; Li, B.-J.; Lu, X.-Y.; Lin, S.; Shi, Z.-J. Angew. Chem., Int. Ed.2009,48, 3817.
(14)Mo,H.;Bao,W.Adv.Synth.Catal.2009,351,2845.
(15)Song,C.-X.;Cai,G-X.;Farrell,T.R.;Jiang,Z.-P.;Li,H.;Gan,L.-B.;Shi,Z.-J. Chem.Commun.2009,6002.
(16)Yang,H.;Sun,P.;Zhu,Y;Yan,H.;Lu,L.;Qu,X.;Li,T；Mao,J.Chem.Commun. 2012,48,7847.
(17)Yang,H.;Yan,H.;Sun,P.;Zhu,Y.;Lu,L.;Liu,D.;Rong,G.;Mao,J.Green Chem. 2013,15,976.
(18)Zhou,S.-L.;Guo,L.-N.;Wang,H.;Duan,X.-H.Chem.Eur.,2013,19,12970.
(19)Zhou,S.-L.;Guo,L.-N.;Wang,S.;Duan,X.-H.Chem.Commun.2014,50,3589.
(20)Correia,C.A.;Li,C.-J.Adv.Synth.Cata.2010,352,1446.
(21)Feng,J.;Liang,S.；Chen,S.-Y.;Zhang,J.;Fu,S.-S.;Yu,X.-Q.Adv.Synth.Catal. 2012,354,1287.
(22)Shi,E.;Shao,Y.;Chen,S.;Hu,H.;Liu,Z.;Zhang,J.;Wan,X.Org.Lett.2012,14, 3384.
(23)Rout,S.K.;Guin,S.;Ghara,K.K.;Banerjee,A.;Patel,B.K.Org.Lett.2012,14, 3982.
(24)Liu,L.;Yun,L.;Wang,Z.;Fu,X.;Yah,C.-h.Tetrahedron Lett.2013,54,5383.
(25)Majji,G.;Guin,s.;Gogoi,A.;Rout,S.K.;Patel,B.K.Chem.Commun.2013,49 3031.
(26)Li,Z.;Li,C.-J.Eur.J.Org.Chem.2005,2005,3173.
(27)Zhao,L.;Li,C.-J.Angew.Chem.,Int. Ed.2008,47,7075.
(28)Xie,J.;Huang,Z.-Z.Angew Chem.,Int Ed.2010,49,10181.
(29)Yang,F.;Li,J.;Xie,J.;Huang,Z.-Z.Org.Lett.2010,12,5214.
(30)Sud,A.;Sureshkumar,D.;Klussmann,M.Chem.Commun.2009,3169.
(31)Zhang,G;Wang,S.;Ma,Y:;Kong,W.;Wang,R.Adv.Synth.Catal.2013,355,874.
(32)Nobuta,T.;Tada,N.;Fujiya,A.;Kauriya,A.;Miura,T.;Itoh,A.Org.Lett.2013,15, 574.
(33)Li,Z.;Li,C.-J.J.Am.Chem.Soc.2005,127,3672.
(34)Basle,O.;Li,C.-J.Green Chem.2007,9,1047.
(35)Condie, A. G.; Gonzalez-Gomez, J. C.; Stephenson, C. R. J. J. Am. Chem. Soc.2010, 132,1464.
(36)Dhineshkumar, J.; Lamani, M.; Alagiri, K.; Prabhu, K. R. Org. Lett.2013,15,1092.
(37)Li, Z.; Li, C.-J. J. Am. Chem. Soc.2005,127,6968.
(38)Alagiri, K.; Kumara, G. S. R.; Prabhu, K. R. Chem. Commun.2011,47,11787.
(39)Huang, L.; Niu, T.; Wu, J.; Zhang, Y. J. Org. Chem.2011,76,1759.
(40)Catino, A. J.; Nichols, J. M.; Nettles, B. J.; Doyle, M. P. J. Am. Chem. Soc.2006, 128,5648.
(41)Ratnikov, M. O.; Xu, X.; Doyle, M. P. J. Am. Chem. Soc.2013,135,9475.
(42)Shirakawa, E.; Uchiyama, N.; Hayashi, T. J. Org. Chem.2010,76,25.
(43)Li, L.-T.; Huang, J.; Li, H.-Y.; Wen, L.-J.; Wang, P.; Wang, B. Chem. Commun.2012, 48,5187.
(44)Chen, J.; Liu, B.; Liu, D.; Liu, S.; Cheng, J. Adv. Synth. Catal.2012,354,2438.
(45)Wu, J.-C.; Song, R.-J.; Wang, Z.-Q.; Huang, X.-C.; Xie, Y.-X.; Li, J.-H. Angew. Chem., Int. Ed.2012,51,3453.
(46)Li,K.; Tan, G.; Huang, J.; Song, E.; You, J. Angew. Chem., Int. Ed. 2013,52,12942.
(47)Li, Z.; Bohle, D. S.; Li, C.-J. Proc. Natl. Acad. Sci. U.S.A.2006,103,8928.
(48)Sureshkumar, D.; Sud, A.; Klussmann, M. Synlett 2009,1558.
(49)Chu, L.; Zhang, X.; Qing, F.-L. Org. Lett.2009,11,2197.
(50)Li, Z. P.; Li, C. J. J. Am. Chem. Soc.2004,126,11810.
(51)Zhao, L.; Li, C. J. Angew. Chem., Int. Ed.2008,47,7075.
(52)Zheng, Q.-H.; Meng, W.; Jiang, G.-J.; Yu, Z.-X. Org. Lett.2013,15,5928.
(53)Han, W.; Ofial, A. R. Chem. Commun.2009,5024.
(54)Zhang, Y.; Peng, H.; Zhang, M.; Cheng, Y.; Zhu, C. Chem. Commun.2011,47,2354.
(55)Liu, L.; Wang, Z.; Fu, X.; Yan, C.-H. Org. Lett.2012,14,5692.
(56)Sakai, N.; Mutsuro, A.; Ikeda, R.; Konakahara, T. Synlett 2013,24,1283.
(57)Zhang, C.; Liu, C.; Shao, Y.; Bao, X.; Wan, X. Chem. Eur. J.2013,19,17917.
(58)a) Baudy, R. B.; Fletcher, H.; Yardley, J. P.; Zaleska, M. M.; Bramlett, D. R.; Tasse, R. P.; Kowal, D. M.; Katz, A. H.; Moyer, J. A.; Abou-Gharbia, M. J. Med. Chem.2001, 44,1516; b) Hauel, N. H.; Nar, H.; Priepke, H.; Ries, U.; Stassen, J. M.; Wienen, W. J. Med. Chem.2002,45,1757; c) Velik, J.; Baliharova, V.; Fink-Gremmels, J.; Bull, S.; Lamka, J.; Skalova, L. Res. Vet. Sci.2004,76,95; d) Anderson, E. B.; Long, T. E. Polymer.2010,51,2447.
(59)a) Diez-Gonzalez, S.; Marion, N.; Nolan, S. P. Chem. Rev.2009,109,3612; b) Benhamou, L.; Chardon, E.; Lavigne, G.; Bellemin-Laponnaz, S.; Cesar, V. Chem. Rev. 2011,111,2705; c) Pinkert, A.; Marsh, K. N.; Pang, S. S.; Staiger, M. P. Chem. Rev.2009, 109,6712; d) Martins, M. A. P.; Frizzo, C. P.; Moreira, D. N.; Zanatta, N.; Bonacorso, H. G Chem. Rev.2008,108,2015.
(60)Pelletier, G.; Powell, D. A. Org. Lett.2006,8,6031.
(61)Powell, D. A.; Fan, H. J. Org. Chem.2010,75,2726.
(62)Wang, Z.; Zhang, Y. M.; Fu, H.; Jiang, Y. Y.; Zhao, Y. F. Org. Lett.2008,10,1863.
(63)Cundari, T. R.; Wiese, S.; Badiei, Y. M.; Gephart, R. T.; Mossin, S.; Varonka, M. S.; Melzer, M. M.; Meyer, K.; Warren, T. H. Angew. Chem., Int. Ed.2010,49,8850.
(64)Gephart, R. T.; Huang, D. L.; Aguila, M. J. B.; Schmidt, G.; Shahu, A.; Warren, T. H. Angew. Chem., Int. Ed.2012,57,6488.
(65)Ye, Y. H.; Zhang, J.; Wang, G.; Chen, S. Y.; Yu, X. Q. Tetrahedron 2011,67,4649.
(66)a) Cheng, D.; Bao, W. J. Org. Chem.2008,73,6881; b) Mo, H. J.; Bao, W. L. J. Org. Chem.2010,75,4856; c) He, L.; Yu, J.; Zhang, J.; Yu, X. Q. Org. Lett.2007,9,2277.
(67)a) Collet, F.; Dodd, R. H.; Dauban, P. Chem. Commun.2009,5061; b) Zalatan, D. N.; Du Bois, J. Top. Curr. Chem.2010,292,347.
(68)Zhang, Y M.; Fu, H.; Jiang, Y. Y; Zhao, Y F. Org. Lett.2007,9,3813.
(69)Liu, X. W.; Zhang, Y M.; Wang, L.; Fu, H.; Jiang, Y. Y; Zhao, Y. F. J. Org. Chem. 2008,73,6207.
(70)Mao, X. R.; Wu, Y. Z.; Jiang, X. X.; Liu, X. H.; Cheng, Y. X.; Zhu, C. J. Rsc. Adv. 2012,2,6733.
(71)Lao, Z. Q.; Zhong, W. H.; Lou, Q. H.; Li, Z. J.; Meng, X. B. Org. Biomo.l Chem. 2012,10,7869.
(72)Pan, S. G.; Liu, J. H.; Li, H. R.; Wang, Z. Y.; Guo, X. W.; Li, Z. P. Org. Lett.2010, 12,1932.
(73)a) Naota, T.; Nakato, T.; Murahashi, S. I. Tetrahedron Lett.1990,31,7475; b) Wang, D. H.; Hao, X. S.; Wu, D. F.; Yu, J. Q. Org. Lett.2006,8,3387; c) Wei, Y.; Ding, H. Q.; Lin, S. X.; Liang, F. S. Org. Lett.2011,13,1674.
(74)a) Humphrey, J. M.; Chamberlin, A. R. Chem Rev 1997,97,2243; b) Fletcher, M. D.; Campbell, M. M. Chem Rev 1998,98,763.
(75)a) Park, J. D.; Englert, R. D.; Meek, J. S. J. Am. Chem. Soc.1952,74,1010; b) Isele, G. L.; Luttring. A Synthesis 1971,266; c) Johnstone, R. A. W.; Rose, M. E. Tetrahedron 1979,35,2169; d) Gajda, T.; Zwierzak, A. Synthesis 1981,1005.
(76)a) Otera, J. Chem. Rev.1993,93,1449; b) Otera, J. Angew. Chem., Int. Ed 2001,40, 2044.
(77)Rosa, J. N.; Reddy, R. S.; Candeias, N. R.; Cal, P. M. S. D.; Gois, P. M. P. Org. Lett. 2010,12,2686.
(78)Liu, C.; Tang, S.; Zheng, L. W.; Liu, D.; Zhang, H.; Lei, A. W. Angew. Chem., Int. Ed.2012,51,5662.
(79)Chen, L.; Shi, E. B.; Liu, Z. J.; Chen, S. L.; Wei, W.; Li, H.; Xu, K.; Wan, X. B. Chem. Eur. J.2011,17,4085.
(80)Feng, J.; Liang, S.; Chen, S. Y.; Zhang, J.; Fu, S. S.; Yu, X. Q. Adv. Synth. Catal. 2012,354,1287.
(81)Shi, E. B.; Shao, Y; Chen, S. L.; Hu, H. Y; Liu, Z. J.; Zhang, J.; Wan, X. B. Org. Lett. 2012,14,3384.
(82)a) Kochi, J. K. J. Am. Chem. Soc.1962,84,1193; b) Zhang, Y H.; Feng, J. Q.; Li, C. J. J. Am. Chem. Soc.2008,130,2900; c) Gephart, R. T.; McMullin, C. L.; Sapiezynski, N. G.; Jang, E. S.; Aguila, M. J. B.; Cundari, T. R.; Warren, T. H. J. Am. Chem. Soc.2012, 134,17350.
(2)a) Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev.2003,103,2861; b) Miiller, P.; Fruit, C. Chem. Rev.2003,103,2905; c) Davies, H. M. L.; Manning, J. R. Nature 2008, 451,417.
(3)Boutadla, Y.; Davies, D. L.; Macgregor, S. A.; Poblador-Bahamonde, A. I. Dalton Trans.2009,5820.
(4)a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev.2007,107,174; b) Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed.2009,48,9792; c) Le Bras, J.; Muzart, J. Chem. Rev.2011,111,1170.
(5)a) Diaz-Requejo, M. M.; Perez, P. J. Chem. Rev.2008,108,3379; b) Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev.2009,38,3242; c) Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem. Eur. J.2010,16,2654; d) Baudoin, O. Chem. Soc. Rev.2011,40,4902; e) Ramirez, T. A.; Zhao, B.; Shi, Y. Chem. Soc. Rev.2012,41,931; f) Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed.2013,52,
11726.
(6)a) Li, C. J. Acc. Chem. Res.2009,42,335; b) Yoo, W. J.; Li, C. J. Top. Curr. Chem. 2010,292,281; c) Scheuermann, C. J. Chem. Eur. J.2010,5,436; d) Ashenhurst, J. A. Chem. Soc. Rev.2010,39,540; e) Yeung, C. S.; Dong, V. M. Chem. Rev.2011, 111,1215; f) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev.2011,40,5068; g) Jones, K. M.; Klussmann, M. Synlett 2012,23,159. (7) Li, Z.; Li, C.-J.J. Am. Chem. Soc.2005,128,56.
(8)Li, Z.; Cao, L.; Li, C.-J. Angew. Chem., Int. Ed.2007,46,6505.
(9)Correia, C. A.; Li, C.-J. Tetrahedron Lett.2010,51,1172.
(10)Borduas, N.; Powell, D. A. J. Org. Chem.2008,73,7822.
(11)Cheng, D.; Bao, W. Adv. Synth. Catal.2008,350,1263.
(12)Pinter, A.; Sud, A.; Sureshkumar, D.; Klussmann, M. Angew. Chem., Int. Ed.2010, 49,5004.
(13)Li, Y.-Z.; Li, B.-J.; Lu, X.-Y.; Lin, S.; Shi, Z.-J. Angew. Chem., Int. Ed.2009,48, 3817.
(14)Mo,H.;Bao,W.Adv.Synth.Catal.2009,351,2845.
(15)Song,C.-X.;Cai,G-X.;Farrell,T.R.;Jiang,Z.-P.;Li,H.;Gan,L.-B.;Shi,Z.-J. Chem.Commun.2009,6002.
(16)Yang,H.;Sun,P.;Zhu,Y;Yan,H.;Lu,L.;Qu,X.;Li,T；Mao,J.Chem.Commun. 2012,48,7847.
(17)Yang,H.;Yan,H.;Sun,P.;Zhu,Y.;Lu,L.;Liu,D.;Rong,G.;Mao,J.Green Chem. 2013,15,976.
(18)Zhou,S.-L.;Guo,L.-N.;Wang,H.;Duan,X.-H.Chem.Eur.,2013,19,12970.
(19)Zhou,S.-L.;Guo,L.-N.;Wang,S.;Duan,X.-H.Chem.Commun.2014,50,3589.
(20)Correia,C.A.;Li,C.-J.Adv.Synth.Cata.2010,352,1446.
(21)Feng,J.;Liang,S.；Chen,S.-Y.;Zhang,J.;Fu,S.-S.;Yu,X.-Q.Adv.Synth.Catal. 2012,354,1287.
(22)Shi,E.;Shao,Y.;Chen,S.;Hu,H.;Liu,Z.;Zhang,J.;Wan,X.Org.Lett.2012,14, 3384.
(23)Rout,S.K.;Guin,S.;Ghara,K.K.;Banerjee,A.;Patel,B.K.Org.Lett.2012,14, 3982.
(24)Liu,L.;Yun,L.;Wang,Z.;Fu,X.;Yah,C.-h.Tetrahedron Lett.2013,54,5383.
(25)Majji,G.;Guin,s.;Gogoi,A.;Rout,S.K.;Patel,B.K.Chem.Commun.2013,49 3031.
(26)Li,Z.;Li,C.-J.Eur.J.Org.Chem.2005,2005,3173.
(27)Zhao,L.;Li,C.-J.Angew.Chem.,Int. Ed.2008,47,7075.
(28)Xie,J.;Huang,Z.-Z.Angew Chem.,Int Ed.2010,49,10181.
(29)Yang,F.;Li,J.;Xie,J.;Huang,Z.-Z.Org.Lett.2010,12,5214.
(30)Sud,A.;Sureshkumar,D.;Klussmann,M.Chem.Commun.2009,3169.
(31)Zhang,G;Wang,S.;Ma,Y:;Kong,W.;Wang,R.Adv.Synth.Catal.2013,355,874.
(32)Nobuta,T.;Tada,N.;Fujiya,A.;Kauriya,A.;Miura,T.;Itoh,A.Org.Lett.2013,15, 574.
(33)Li,Z.;Li,C.-J.J.Am.Chem.Soc.2005,127,3672.
(34)Basle,O.;Li,C.-J.Green Chem.2007,9,1047.
(35)Condie, A. G.; Gonzalez-Gomez, J. C.; Stephenson, C. R. J. J. Am. Chem. Soc.2010, 132,1464.
(36)Dhineshkumar, J.; Lamani, M.; Alagiri, K.; Prabhu, K. R. Org. Lett.2013,15,1092.
(37)Li, Z.; Li, C.-J. J. Am. Chem. Soc.2005,127,6968.
(38)Alagiri, K.; Kumara, G. S. R.; Prabhu, K. R. Chem. Commun.2011,47,11787.
(39)Huang, L.; Niu, T.; Wu, J.; Zhang, Y. J. Org. Chem.2011,76,1759.
(40)Catino, A. J.; Nichols, J. M.; Nettles, B. J.; Doyle, M. P. J. Am. Chem. Soc.2006, 128,5648.
(41)Ratnikov, M. O.; Xu, X.; Doyle, M. P. J. Am. Chem. Soc.2013,135,9475.
(42)Shirakawa, E.; Uchiyama, N.; Hayashi, T. J. Org. Chem.2010,76,25.
(43)Li, L.-T.; Huang, J.; Li, H.-Y.; Wen, L.-J.; Wang, P.; Wang, B. Chem. Commun.2012, 48,5187.
(44)Chen, J.; Liu, B.; Liu, D.; Liu, S.; Cheng, J. Adv. Synth. Catal.2012,354,2438.
(45)Wu, J.-C.; Song, R.-J.; Wang, Z.-Q.; Huang, X.-C.; Xie, Y.-X.; Li, J.-H. Angew. Chem., Int. Ed.2012,51,3453.
(46)Li,K.; Tan, G.; Huang, J.; Song, E.; You, J. Angew. Chem., Int. Ed. 2013,52,12942.
(47)Li, Z.; Bohle, D. S.; Li, C.-J. Proc. Natl. Acad. Sci. U.S.A.2006,103,8928.
(48)Sureshkumar, D.; Sud, A.; Klussmann, M. Synlett 2009,1558.
(49)Chu, L.; Zhang, X.; Qing, F.-L. Org. Lett.2009,11,2197.
(50)Li, Z. P.; Li, C. J. J. Am. Chem. Soc.2004,126,11810.
(51)Zhao, L.; Li, C. J. Angew. Chem., Int. Ed.2008,47,7075.
(52)Zheng, Q.-H.; Meng, W.; Jiang, G.-J.; Yu, Z.-X. Org. Lett.2013,15,5928.
(53)Han, W.; Ofial, A. R. Chem. Commun.2009,5024.
(54)Zhang, Y.; Peng, H.; Zhang, M.; Cheng, Y.; Zhu, C. Chem. Commun.2011,47,2354.
(55)Liu, L.; Wang, Z.; Fu, X.; Yan, C.-H. Org. Lett.2012,14,5692.
(56)Sakai, N.; Mutsuro, A.; Ikeda, R.; Konakahara, T. Synlett 2013,24,1283.
(57)Zhang, C.; Liu, C.; Shao, Y.; Bao, X.; Wan, X. Chem. Eur. J.2013,19,17917.
(58)a) Baudy, R. B.; Fletcher, H.; Yardley, J. P.; Zaleska, M. M.; Bramlett, D. R.; Tasse, R. P.; Kowal, D. M.; Katz, A. H.; Moyer, J. A.; Abou-Gharbia, M. J. Med. Chem.2001, 44,1516; b) Hauel, N. H.; Nar, H.; Priepke, H.; Ries, U.; Stassen, J. M.; Wienen, W. J. Med. Chem.2002,45,1757; c) Velik, J.; Baliharova, V.; Fink-Gremmels, J.; Bull, S.; Lamka, J.; Skalova, L. Res. Vet. Sci.2004,76,95; d) Anderson, E. B.; Long, T. E. Polymer.2010,51,2447.
(59)a) Diez-Gonzalez, S.; Marion, N.; Nolan, S. P. Chem. Rev.2009,109,3612; b) Benhamou, L.; Chardon, E.; Lavigne, G.; Bellemin-Laponnaz, S.; Cesar, V. Chem. Rev. 2011,111,2705; c) Pinkert, A.; Marsh, K. N.; Pang, S. S.; Staiger, M. P. Chem. Rev.2009, 109,6712; d) Martins, M. A. P.; Frizzo, C. P.; Moreira, D. N.; Zanatta, N.; Bonacorso, H. G Chem. Rev.2008,108,2015.
(60)Pelletier, G.; Powell, D. A. Org. Lett.2006,8,6031.
(61)Powell, D. A.; Fan, H. J. Org. Chem.2010,75,2726.
(62)Wang, Z.; Zhang, Y. M.; Fu, H.; Jiang, Y. Y.; Zhao, Y. F. Org. Lett.2008,10,1863.
(63)Cundari, T. R.; Wiese, S.; Badiei, Y. M.; Gephart, R. T.; Mossin, S.; Varonka, M. S.; Melzer, M. M.; Meyer, K.; Warren, T. H. Angew. Chem., Int. Ed.2010,49,8850.
(64)Gephart, R. T.; Huang, D. L.; Aguila, M. J. B.; Schmidt, G.; Shahu, A.; Warren, T. H. Angew. Chem., Int. Ed.2012,57,6488.
(65)Ye, Y. H.; Zhang, J.; Wang, G.; Chen, S. Y.; Yu, X. Q. Tetrahedron 2011,67,4649.
(66)a) Cheng, D.; Bao, W. J. Org. Chem.2008,73,6881; b) Mo, H. J.; Bao, W. L. J. Org. Chem.2010,75,4856; c) He, L.; Yu, J.; Zhang, J.; Yu, X. Q. Org. Lett.2007,9,2277.
(67)a) Collet, F.; Dodd, R. H.; Dauban, P. Chem. Commun.2009,5061; b) Zalatan, D. N.; Du Bois, J. Top. Curr. Chem.2010,292,347.
(68)Zhang, Y M.; Fu, H.; Jiang, Y. Y; Zhao, Y F. Org. Lett.2007,9,3813.
(69)Liu, X. W.; Zhang, Y M.; Wang, L.; Fu, H.; Jiang, Y. Y; Zhao, Y. F. J. Org. Chem. 2008,73,6207.
(70)Mao, X. R.; Wu, Y. Z.; Jiang, X. X.; Liu, X. H.; Cheng, Y. X.; Zhu, C. J. Rsc. Adv. 2012,2,6733.
(71)Lao, Z. Q.; Zhong, W. H.; Lou, Q. H.; Li, Z. J.; Meng, X. B. Org. Biomo.l Chem. 2012,10,7869.
(72)Pan, S. G.; Liu, J. H.; Li, H. R.; Wang, Z. Y.; Guo, X. W.; Li, Z. P. Org. Lett.2010, 12,1932.
(73)a) Naota, T.; Nakato, T.; Murahashi, S. I. Tetrahedron Lett.1990,31,7475; b) Wang, D. H.; Hao, X. S.; Wu, D. F.; Yu, J. Q. Org. Lett.2006,8,3387; c) Wei, Y.; Ding, H. Q.; Lin, S. X.; Liang, F. S. Org. Lett.2011,13,1674.
(74)a) Humphrey, J. M.; Chamberlin, A. R. Chem Rev 1997,97,2243; b) Fletcher, M. D.; Campbell, M. M. Chem Rev 1998,98,763.
(75)a) Park, J. D.; Englert, R. D.; Meek, J. S. J. Am. Chem. Soc.1952,74,1010; b) Isele, G. L.; Luttring. A Synthesis 1971,266; c) Johnstone, R. A. W.; Rose, M. E. Tetrahedron 1979,35,2169; d) Gajda, T.; Zwierzak, A. Synthesis 1981,1005.
(76)a) Otera, J. Chem. Rev.1993,93,1449; b) Otera, J. Angew. Chem., Int. Ed 2001,40, 2044.
(77)Rosa, J. N.; Reddy, R. S.; Candeias, N. R.; Cal, P. M. S. D.; Gois, P. M. P. Org. Lett. 2010,12,2686.
(78)Liu, C.; Tang, S.; Zheng, L. W.; Liu, D.; Zhang, H.; Lei, A. W. Angew. Chem., Int. Ed.2012,51,5662.
(79)Chen, L.; Shi, E. B.; Liu, Z. J.; Chen, S. L.; Wei, W.; Li, H.; Xu, K.; Wan, X. B. Chem. Eur. J.2011,17,4085.
(80)Feng, J.; Liang, S.; Chen, S. Y.; Zhang, J.; Fu, S. S.; Yu, X. Q. Adv. Synth. Catal. 2012,354,1287.
(81)Shi, E. B.; Shao, Y; Chen, S. L.; Hu, H. Y; Liu, Z. J.; Zhang, J.; Wan, X. B. Org. Lett. 2012,14,3384.
(82)a) Kochi, J. K. J. Am. Chem. Soc.1962,84,1193; b) Zhang, Y H.; Feng, J. Q.; Li, C. J. J. Am. Chem. Soc.2008,130,2900; c) Gephart, R. T.; McMullin, C. L.; Sapiezynski, N. G.; Jang, E. S.; Aguila, M. J. B.; Cundari, T. R.; Warren, T. H. J. Am. Chem. Soc.2012, 134,17350.