SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2017 , Vol. 37 >Issue 1: 1 - 19

DOI: https://doi.org/10.6023/cjoc201607040

REVIEW

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).

Fold

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.

Key words： tertiary amines; visible light; photoredox catalysis; C-H functionalization

Cite this article

Liu Wei , Zheng Xinyu , Zeng Jianguo , Cheng Pi . Visible Light Promoted C-H Functionalization Reactions of Tertiary Amines[J]. Chinese Journal of Organic Chemistry, 2017 , 37(1) : 1 -19 . DOI: 10.6023/cjoc201607040

References

[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.

Options
Outlines

/

〈 〉