可见光催化脱羧偶联反应研究进展

doi:10.6023/cjoc201601012

摘要/Abstract

可见光介入的偶联反应近年来得到了广泛的关注，已经发展成C—H活化、构建新型C—C、C—X键的重要方法之一. 可见光催化体系的发展也为脱羧偶联反应提供了新的手段，许多关于可见光催化的脱羧反应研究见诸报端. 对近年来可见光催化的脱羧反应进行了简要概述.

关键词: 可见光催化, 脱羧, 偶联反应

Visible light mediated coupling reaction has obtained the widespread attention in recent years, and has been a most efficient method for building new C—C and C—X bonds. The development of visible light catalytic system also has provided a new means for decarboxylation reaction. Lots of studies on visible light catalytic decarboxylation reaction were published recently. In this paper, the visible light mediated decarboxylation reactions in recent years are briefly reviewed.

Key words: visible light catalysis, decarboxylation, coupling reaction

引用此文

关保川, 许孝良, 王红, 李小年. 可见光催化脱羧偶联反应研究进展[J]. 有机化学, 2016, 36(7): 1564-1571.

Guan Baochuan, Xu Xiaoliang, Wang Hong, Li Xiaonian. Progress on the Decarboxylation Coupling Reaction Mediated by Visible Light[J]. Chinese Journal of Organic Chemistry, 2016, 36(7): 1564-1571.

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参考文献

[1] Weaver, J. D; Recio, A; Grenning, A. J; Tunge, J. A. Chem. Rev. 2011, 111, 1846.
[2] Baudoin, O. Angew. Chem., Int. Ed. 2007, 46, 1373;
[3] Li, Z.; Jiang, Y. Y; Yeagley, A. A.; Bour, J. P.; Liu, L.; Chruma, J. J.; Fu, Y. Chem. Eur. J. 2012, 18, 14527.
[4] Burger, E. C.; Tunge, J. A. J. Am. Chem. Soc. 2006, 128, 10002.
[5] Yeagley, A. A.; Chruma, J. J. Org. Lett. 2007, 9, 2879.
[6] Xie, J.; Jin, H.; Xu, P.; Zhu, C. Tetrahedron Lett. 2014, 55, 36.
[7] Chen, J.; Cen, J.; Xu, X. L.; Li, X. N. Catal. Sci. Technol. 2016, 6, 349.
[8] Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77.
[9] Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875.
[10] Pirnot, M. T.; Rankic, D. A.; Martin, D. B. C.; MacMillan, D. W. C. Science 2013, 339, 1593.
[11] McNally, A.; Prier, C. K.; MacMillan, D. W. C. Science 2011, 334, 1114.
[12] Shih, H. W.; Wal, M. N. V.; Grange, R. L.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 13600.
[13] Jeffrey, J.; Petronijevic, F. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 8404.
[14] Ischay, M. A.; Anzovino, M. E.; Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 12886.
[15] Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2009, 131, 14604.
[16] Lin, S.; Ischay, M. A.; Fry, C. G.; Yoon, T. P. J. Am. Chem. Soc. 2011, 133, 19350.
[17] Lu, Z.; Yoon, T. P. Angew. Chem., Int. Ed. 2012, 51, 10329.
[18] Blum, T. R.; Zhu, Y.; Nordeen, S. A.; Yoon, T. P. Angew. Chem., Int. Ed. 2014, 53, 11056.
[19] Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. J. Am. Chem. Soc. 2009, 131, 8756.
[20] Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102.
[21] Condie, A. G.; Gonzalez-Gomez, J. C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2010, 132, 1464.
[22] Freeman, D. B.; Furst, L.; Condie, A. G.; Stephenson, C. R. J. Org. Lett. 2012, 14, 94.
[23] Xuan, J.; Cheng, Y.; An, J.; Lu, L. Q.; Zhang, X. X.; Xiao, W. J. Chem. Commun. 2011, 47, 8337.
[24] Zou, Y. Q.; Guo, W.; Liu, F. L.; Lu, L. Q.; Chen, J. R.; Xiao, W. J. Green Chem. 2014, 16, 3787.
[25] Xuan, J.; Xia, X. D.; Zeng, T. T.; Feng, Z. J.; Chen, J. R.; Lu, L. Q.; Xiao, W. J. Angew. Chem., Int. Ed. 2014, 53, 5633.
[26] Xie J.; Xu P.; Li, H.; Xue, Q.; Jin, H.; Cheng, Y.; Zhu, C. Chem. Commun. 2013, 49, 5672.
[27] Xuan, J.; Zhang, Z. G.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 15632.
[28] Zuo, Z.-W.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 5257
[29] Lloyd-Jones, G. C.; Ball, L. T. Science 2014, 345, 381.
[30] Terrett, J. A.; Cuthbertson, J. D.; Shurtleff1, V. W.; MacMillan, D. W. C. Nature 2015, 524, 330.
[31] Hopkinson, M. N.; Sahoo, B.; Glorius, F. Adv. Synth. Catal. 2014, 356, 2794.
[32] Tellis, J. C. Primer, D. N.; Molander, G. A. Science 2014, 345, 433.
[33] Cai, S.Y.; Yang, K.; Wang, D. Z. Org. Lett. 2014, 16, 2606.
[34] Choi, S.; Chatterjee, T.; Choi, W. J.; You, Y.; Cho, D. E. J. ACS Catal. 2015, 5, 4796.
[35] Shu, X. Z.; Zhang, M.; He, Y.; Frei, H.; Toste, F. D. J. Am. Chem. Soc. 2014, 136, 5844.
[36] Anderson, A. J. M.; Koehi, J. K. J. Am. Chem. Soc. 1970, 92, 1651.
[37] Miller, J. A.; Nelson, J. A.; Byrne, M. P. J. Org. Chem. 1993, 58, 18.
[38] Samuel, C.; Simone, T.; Mueller, J.; Jerome, L. Angew. Chem., Int. Ed. 2007, 46, 2082.
[39] Burger, E. C.; Tunge. J. A. Chem. Commun. 2005, 2835.
[40] Zuo, Z.; Ahneman, D. T.; Chu, L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437.
[41] Oderinde, M. S.; Varela-Alvarez, A.; Aquila, B.; Robbins, D. W.; Johannes, J. W. J. Org. Chem. 2015, 80, 7642.
[42] Chu, L.; Lipshultz, J. M.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 7929.
[43] Cheng, W. M.; Shang, R.; Yu, H. Z.; Fu, Y. Chem. Eur. J. 2015, 21, 13191.
[44] Noble, A.; McCarver, S. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 624.
[45] Zou, Y. Q.; Duan, S. W.; Meng, X. G.; Hu, X. Q.; Gao, S.; Chen, J. R. Xiao, W. J. Tetrahedron 2012, 68, 6914.
[46] Tucker, J. W.; Narayanam, J. M. R.; Krabbe, S. W.; Stephenson, C. R. J. Org. Lett. 2010, 12, 368.
[47] Furst, L.; Matsuura, B. S.; Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. Org. Lett. 2010, 12, 3104.
[48] Furst, L.; Narayanam, J. M. R.; Stephenson, C. R. J. Angew. Chem., Int. Ed. 2011, 50, 9655.
[49] Ju, X.; Liang, Y.; Jia, P.; Li, W.; Yu, W. Org. Biomol. Chem. 2012, 10, 498.
[50] Maity, S.; Zheng, N. Angew. Chem., Int. Ed. 2012, 51, 9562.
[51] Chen, M.; Huang, Z. T.; Zheng, Q. Y. Chem. Commun. 2012, 48, 11686.
[52] Fu, W.; Xu, F.; Fu, Y.; Zhu, M.; Yu, J.; Xu, C.; Zou, D. J. Org. Chem. 2013, 78, 12202.
[53] Zhang, P.; Xiao, T.; Xiong, S.; Dong, X.; Zhou, L. Org. Lett. 2014, 16, 3294.
[54] Gu, L.; Jin, C.; Liu, J.; Zhang, H.; Yuan, M.; Li, G. Green Chem. 2016, 18, 1201.
[55] Noble, A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 11602
[56] Huang, H.; Jia, K.; Chen, Y. Angew. Chem., Int. Ed. 2015, 54, 1881.
[57] Rueping, M.; Koenigs, R. M.; Poscharny, K.; Fabry, D. C. Leonori, D.; Vila, C. Chem. Eur. J. 2012, 18, 5170.
[58] Adrian, T. A.; Matthew, N. H.; Basudev, S.; Frank, G. Chem. Sci. 2016, 7, 89.
[59] Kim, S.; Martin, J. R.; Toste, F. D. Chem. Sci. 2016, 7, 85.
[60] Yang, J.; Zhang, J.; Qi, L.; Hu, C.; Chen, Y. Chem. Commun. 2015, 51, 5275.
[61] Huang, H.; Zhang, G.; Chen, Y. Angew. Chem., Int. Ed. 2015, 54, 7872.
[62] Zhou, Q. Q.; Guo, W.; Ding, W.; Wu, X.; Chen, X.; Lu, L. Q.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 11196.
[63] Guo, W.; Lu, L. Q.; Wang, Y.; Wang, Y. N.; Chen, J. R.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 2265.
[64] Majek, M.; Wangelin, A. J. Angew. Chem., Int. Ed. 2015, 54, 2270.
[65] Vaillant, F. L.; Courant, T.; Waser, J. Angew. Chem., Int. Ed. 2015, 54, 11200.
[66] Tan, H.; Li, H.; Ji, W.; Wang, L. Angew. Chem., Int. Ed. 2015, 54, 8374.
[67] Miyake, Y.; Nakajima, K.; Nishibayashi, Y. Chem. Commun. 2013, 49, 7854.
[68] Chu, L.; Ohta, C.; Zuo, Z.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 10886.
[69] Lackner, G. L.; Quasdorf, K. W.; Overman, L. E. J. Am. Chem. Soc. 2013, 135, 15342.
[70] Lackner, G. L.; Quasdorf, K. W.; Pratsch, G.; Overman, L. E. J. Org. Chem. 2015, 80, 6012.
[71] Nawrat, C. C.; Jamison, C. R.; Slutskyy, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 11270.
[72] Wang, G. Z.; Shang, R.; Cheng, W. M.; Fu, Y. Org. Lett. 2015, 17, 4830.
[73] Ji, W.; Tan, H.; Wang, M.; Li, P.; Wang, L. Chem. Commun. 2016, 52, 1201.
[74] Lang, S. B.; O'Nele, K. M.; Tunge, J. A. J. Am. Chem. Soc. 2014, 136, 13606.
[75] Lang, S. B.; ONele, K. M.; Douglas, J. T.; Tunge, J. A. Chem. Eur. J. 2015, 21, 18589.
[76] Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
[77] Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2015, 54, 3216.
[78] Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
[79] Nagib1, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224.
[80] Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034.
[81] Sahoo, B.; Li, J. L.; Glorius, F. Angew. Chem., Int. Ed. 2015, 54, 11577.
[82] Su, Y. M.; Hou, Y.; Yin, F.; Xu, Y. M.; Li, Y.; Zheng, X.; Wang, X. S. Org. Lett. 2014, 16, 2958.
[83] Tomita, R.; Yasu, Y.; Koike, T.; Akita, M. Angew. Chem., Int. Ed. 2014, 53, 7144.
[84] Wolf, M. O.; Sammis, G. M.; Paquin, J. F. J. Am. Chem. Soc. 2014, 136, 2637.
[85] Ventre, S.; Petronijevic, F. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 5654.
[86] Wu, X.; Meng, C.; Yuan, X.; Jia, X.; Qian, X.; Ye. J. Chem. Commun. 2015, 51, 11864.
[87] Cassani, C.; Bergonzini, G.; Wallentin, C. J. Org. Lett. 2014, 16, 4228.
[88] Nguyen, T. M.; Nicewicz, D. A. J. Am. Chem. Soc. 2013, 135, 9588.
[89] Nguyen, T. M.; Manohar, N.; Nicewicz, D. A. Angew. Chem., Int. Ed. 2014, 53, 6198.
[90] Romero, N. A.; Nicewicz, D. A. J. Am. Chem. Soc. 2014, 136, 17024.
[91] Morse, P. D.; Nicewicz, D. A. Chem. Sci. 2015, 6, 270.
[92] Griffin, J. D.; Zeller, M. A.; Nicewicz, D. A. J. Am. Chem. Soc. 2015, 137, 11340.
[93] Liu, J.; Liu, Q.; Yi, H.; Qin, C.; Bai, R.; Qi, X.; Lan, Y. Lei, A. Angew. Chem., Int. Ed. 2014, 53, 502.