综述与进展

可见光促进的叔胺C-H官能团化反应

  • 刘薇 ,
  • 郑昕宇 ,
  • 曾建国 ,
  • 程辟
展开
  • a 湖南农业大学园艺园林学院 兽用中药资源与中兽药创制国家地方联合工程研究中心 长沙 410128;
    b 湖南农业大学 湖南省植物功能成分利用协同创新中心 长沙 410128

收稿日期: 2016-07-27

  修回日期: 2016-09-01

  网络出版日期: 2016-10-09

基金资助

国家自然科学基金(No. 31402109)资助项目.

Visible Light Promoted C-H Functionalization Reactions of Tertiary Amines

  • Liu Wei ,
  • Zheng Xinyu ,
  • Zeng Jianguo ,
  • Cheng Pi
Expand
  • a National and Provincial Union Engineering Research Center for the Veterinary Herbal Medicine Resources and Initiative, College of Horticulture and Landscape Architecture, Hunan Agricultural University, Changsha 410128;
    b Hunan Co-innovation Center for Utilization of Botanicals Functional Ingredients, Hunan Agricultural University, Changsha 410128

Received date: 2016-07-27

  Revised date: 2016-09-01

  Online published: 2016-10-09

Supported by

Project supported by the National Natural Science Foundation of China(No. 31402109).

摘要

叔胺是多种药物分子和天然产物的重要结构组成部分.可见光促进叔胺C-H官能团化反应近年来受到了广泛的关注,为药物分子、生物碱类天然产物的合成提供了便利.基于光氧化还原催化策略,可见光能够诱导叔胺通过单电子转移(SET)过程产生的亚胺正离子或氨基碳自由基中间体,这些中间体能够参与多种类型的有机反应,实现叔胺C-H官能团化.对近年来光氧化还原催化叔胺C-H研究进行了分类和综述.

本文引用格式

刘薇 , 郑昕宇 , 曾建国 , 程辟 . 可见光促进的叔胺C-H官能团化反应[J]. 有机化学, 2017 , 37(1) : 1 -19 . DOI: 10.6023/cjoc201607040

Abstract

The tertiary amine motif is an important structure component of multitudinous natural products and drug molecules.Visible light promoted C-H functionalization of tertiary amines has recently received much attention and facilitated the synthesis of alkaloids and drug molecules.Based on photoredox catalysis,visible light is able to induce the formation of iminium cations or α-amino carbon radicals through single electron transfer process which can participate in multitudinous type of organic reactions and complete C-H functionalization of tertiary amines.In this review,the research progress of photoredox catalytic C-H func-tionalization was categorized and summarized.

参考文献

[1] (a) Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J. Chem. Soc. Rev. 2016, 45, 2044.
(b) Morris, S. A.; Wang, J.; Zhang, N. Acc. Chem. Res. 2016, 49, 1957.
(c) Wei, G.; Basheer, C.; Tan, C.-H.; Jiang, Z. Tetrahedron Lett. 2016, 57, 3801.
(d) Beatty, J. W.; Stephenson, C. R. J. Acc. Chem. Res. 2015, 48, 1474.
(e) Nicewicz, D. A.; Nguyen, T. M. ACS Catal. 2014, 4, 355.
(f) Hari, D. P.; Konig, B. Chem. Commun. 2014, 50, 6688.
(g) Douglas, J. J.; Nguyen, J. D.; Cole, K. P.; Stephenson C. R. J. Aldrichim. Acta 2014, 47, 15.
(h) Prier, C. K.; Rankic, D. A.; McMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
(i) Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828.
(j) Zuo, X.; Wu, W.; Su, W. Acta Chim. Sinica 2015, 73, 1298(in Chinese).(左璇, 吴文亮, 苏伟平, 化学学报, 2015, 73, 1298.)
(k) Sun, X.; Yu, S. Chin. J. Org. Chem. 2016, 36, 239(in Chinese).(孙晓阳, 俞寿云, 有机化学, 2016, 36, 239.)
(l) Tan, R.; Xiao. W. Acta Chim. Sinica 2015, 73, 85(in Chinese).(谭芬, 肖文精, 化学学报, 2015, 73, 85.)
[2] (a) Zenk, M. H. Pure Appl. Chem. 1994, 66, 2023.
(b) Hagel, J. M.; Facchini, P. J. Plant Cell Physiol. 2013, 54,647.
[3] (a) Hedstrand, D. M.; Kruizinga, W. M.; Kellogg, R. M. Tetrahedron Lett. 1978, 19, 1255.
(b) van Bergen, T. J.; Hedstrand, D. M.; Kruizinga, W. H.; Kellogg, R. M. J. Org. Chem. 1979, 44, 4953.
[4] (a) Tang, Q.; Liu, X.; Liu, S.; Xie, H.; Liu, W.; Zeng, J.; Cheng, P. RSC Adv. 2015, 5, 89009.
(b) Schnermann, M. J.; Overman, L. E. Angew. Chem., Int. Ed. 2012, 51, 9576.
(c) Pratsch, G.; Lackner, G. L.; Overman, L. E. J. Org. Chem. 2015, 82, 6025.
(d) Tucker, J. W.; Nguyen, J. D.; Narayanam, J. M. R.; Krabbe, S. W.; Stephenson, C. R. J. Chem. Commun. 2010, 46, 4985.
[5] Freeman, D. B.; Furst, L.; Condie, A. G.; Stephenson, C. R. J. Org. Lett. 2012, 14, 94.
[6] Condie, A. G.; Gonzalez-Gomez, J. C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2010, 132, 1464.
[7] Rueping, M.; Zhua, S.; Koenigs, R. Chem. Commun. 2011, 47, 12709.
[8] Rueping, M.; Koenigs, R. M.; Poscharny, K.; Fabry, D. C.; Leonori, D.; Vila, C. Chem.-Eur. J. 2012, 18, 5170.
[9] Rueping, M.; Zhu, S.; Koenigs, R. M. Chem. Commun. 2011, 47, 8679.
[10] Rueping, M.; Vila, C.; Bootwicha, T. ACS Catal. 2013, 3, 1676.
[11] Pan, Y.; Wang, S.; Kee, C. W.; Dubuisson, E.; Yang, Y.; Loh, K. P.; Tan, C.-H. Green Chem. 2011, 13, 3341.
[12] Feng, Z.-J.; Xuan, J.; Xia, X.-D.; Ding, W.; Guo, W.; Chen, J.-R.; Zou, Y.-Q.; Lu, L.-Q.; Xiao, W.-J. Org. Biomol. Chem. 2014, 12, 2037.
[13] Xiao, T.; Li, L.; Lin, G.; Mao, Z.-W.; Zhou, L. Org. Lett. 2014, 16, 4232.
[14] DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094.
[15] Bergonzini, G.; Schindler, C. S.; Wallentin C.-J.; Jacobsen, E. N.; Stephenson, C. R. J. Chem. Sci. 2014, 5, 112.
[16] Cai, S.; Zhao, X.; Wang, X.; Liu, Q.; Li, Z.; Wang, D. Z. Angew. Chem., Int. Ed. 2012, 51, 8050.
[17] Zhao, Y.; Cai, S.; Li, J.; Wang, D. Z. Tetrahedron 2013, 69, 8129.
[18] Li, X.; Gu, X.; Li, Y.; Li, P. ACS Catal. 2014, 4, 1897.
[19] Beatty, J. W.; Stephenson, C. R. J. J. Am. Chem. Soc. 2014, 136, 10270.
[20] Xuan, J.; Cheng, Y.; An, J.; Lu, L.-Q.; Zhang, X.-X.; Xiao, W.-J. Chem. Commun. 2011, 47, 8337.
[21] Orgren, L. R.; Maverick, E. E.; Marvin, C. J. Org. Chem. 2015, 80, 12635.
[22] Bertrand, S.; Hoffmann, N.; Pete, J.-P. Eur. J. Org. Chem. 2000, 2227.
[23] Miyake, Y.; Nakajima, K.; Nishibayashi, Y. J. Am. Chem. Soc. 2012, 134, 3338.
[24] Zhou, H.; Lu, P.; Gu, X.; Li, P. Org. Lett. 2013, 15, 5646.
[25] Dai, X.; Cheng, D.; Guan, B.; Mao, W.; Xu. X.; Li, X. J. Org. Chem. 2014, 79, 7212.
[26] Dai, X.; Mao, R.; Guan, B.; Xu, X.; Li, X. RSC Adv. 2015, 5, 55290.
[27] Noble, A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 11602.
[28] Kohls, P.; Jadhav, D.; Pandey, G.; Reiser, O. Org. Lett. 2012, 14, 672.
[29] Liu, X.; Ye, X.; Bures, F.; Liu, H.; Jiang, Z. Angew. Chem., Int. Ed. 2015, 54, 11443.
[30] Zhu, S.; Das, A.; Bui, L.; Zhou, H.; Curran, D. P.; Rueping, M. J. Am. Chem. Soc. 2013, 135, 1823.
[31] Zhang, P.; Xiao, T.; Xiong, S.; Dong, X. Zhou, L. Org. Lett. 2014, 16, 3267.
[32] Singh, A.; Arora, A.; Weaver, J. D. Org. Lett. 2013, 15, 5390.
[33] Prier, C. K.; MacMillan, D. W. C. Chem. Sci. 2014, 5, 4173.
[34] Douglas, J. J.; Cole, K. P.; Stephenson, C. R. J. J. Org. Chem. 2014, 79, 11631.
[35] Terrett, J. A.; Clift, M. D.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 6858.
[36] Zou, Y.-Q.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2013, 52, 11701.
[37] Pirnot, M. T.; Rankic, D. A.; Martin, D. B. C.; MacMillan, D. W. C. Science 2013, 339, 1593.
[38] Petronijevic, F. R.; Nappi, M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2013, 135, 18323.
[39] Jeffrey, J. L.; Petronijevic, F. R. MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 8404.
[40] Fava, E.; Millet, A.; Nakajima, M.; Loescher, S.; Rueping, M. Angew. Chem., Int. Ed. 2016, 55, 6776.
[41] Ding, W.; Lu, L.-Q.; Liu, J.; Liu, D.; Song, H.-T.; Xiao, W.-J. J. Org. Chem. 2016, 81, 7237.
[42] Skubi, K. L.; Blum, T. R.; Yoon, T. P. Chem. Rev. 2016, 116, 10035.
[43] Xuan, J.; Zeng, T.-T.; Feng, Z.-J.; Deng, Q.-H.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J. Angew. Chem. Int. Ed. 2015, 54, 1625.
[44] Feng, Z.; Zeng, T.; Xuan, J.; Liu, Y.; Lu, L.; Xiao, W.-J. Sci. China Chem. 2016, 59, 171.
[45] Liu, Z.; Huang, Y.; Xie, H.; Liu, W.; Zeng, J.; Cheng. P. RSC. Adv. 2016, 6, 50500.
[46] Uraguchi, D.; Kinoshita, N.; Kizu, T.; Ooi, T. J. Am. Chem. Soc. 2015, 137, 13768.
[47] Kizu, T.; Uraguchi, D.; Ooi, T. J. Org. Chem. 2016, 81, 6953.
[48] Wang, C.; Qin, J.; Shen, X.; Riedel, R.; Harms, K.; Meggers, E. Angew. Chem., Int. Ed. 2016, 55, 685.
[49] Amador, A. G.; Yoon, T. P. Angew. Chem., Int. Ed. 2016, 55, 2304.
[50] (a) Zhao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2008, 47, 7075.
(b) Wu, J.-C.; Song, R.-J.; Wang, Z.-G.; Huang, X.-C.; Xie, Y.-X.; Li, J.-H. Angew. Chem., Int. Ed. 2012, 51, 3453.
(c) Huo, C.; Yuan, Y.; Wu, M.; Jia, X.; Wang, X.; Chen, F.; Tang, J. Angew. Chem., Int. Ed. 2014, 53, 13544.
(d) Peng, H.; Yu, J.-T.; Jiang, Y.; Yang, H.; Cheng, J. J. Org. Chem. 2014, 79, 9847.
(e) Zhu, Z.-Q.; Bai, P.; Huang, Z.-Z. Org. Lett. 2014, 16, 4881.
[51] Liu, W.; Liu, S.; Xie, H.; Qing, Z.; Zeng, J. Cheng, P. RSC Adv. 2015, 5, 17383.
[52] Zhu, S.; Rueping, M.; Chem. Commun. 2012, 48, 11960.
[53] Zou, Y.-Q.; Lu, L.-Q.; Fu, L.; Chang, N.-J.; Rong, J.; Chen, J.-R. Xiao, W.-J. Angew. Chem., Int. Ed. 2011, 50, 7171.

文章导航

/