Reviews

Recent Advances in Directing Group-Induced C-H Activation Reactions

  • Wang Shan ,
  • Yan Feng ,
  • Wang Liansheng ,
  • Zhu Lei
Expand
  • a School of Chemistry and Materials Science, Hubei Engineering University, Xiaogan 432000;
    b Hubei Collaborative Innovation Center for Biomass Conversion and Utilization, Xiaogan 432000

Received date: 2017-08-26

  Revised date: 2017-09-21

  Online published: 2017-10-24

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21774029, 21304032) and the Natural Science Foundation of Hubei Province (Nos. 2016CFB104, 2015CFC772).

Abstract

C-H bonds are widely existed in almost all the organic compounds. Transition-metal-catalyzed C-H functionalizations usually have high reaction efficiency and high atom-economy. However, traditional strategies based on such transition-metal catalyzed C-H activations generally result in poor selectivities, because C-H bonds in one molecule facilely display similar reactivity. It is difficult to be utilized in preparation of natural products, pharmaceuticals and biomolecules. However, directing group can induce the metal to activate proximal C-H bonds via cyclometallated intermediates, improve the regioselectivity of the transformations. Therefore, it is extremely significant to deveplop auxiliary-induced C-H bonds activations. The research progress of directing group-induced C-H activation reactions and mechanisms for recent ten years are sumarized.

Cite this article

Wang Shan , Yan Feng , Wang Liansheng , Zhu Lei . Recent Advances in Directing Group-Induced C-H Activation Reactions[J]. Chinese Journal of Organic Chemistry, 2018 , 38(2) : 291 -303 . DOI: 10.6023/cjoc201708055

References

[1] Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
[2] Wencel-Delord, J.; Dröge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740.
[3] Ackermann, L. Acc. Chem. Res. 2014, 47, 281.
[4] Moritanl, I.; Fujiwara, Y. Tetrahedron Lett. 1967, 8, 1119.
[5] Bergman, R. G. Nature 2007, 446, 391.
[6] Kleiman, J. P.; Dubeck, M. J. Am. Chem. Soc. 1963, 85, 1544.
[7] Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. 1997, 36, 1740.
[8] Duan, S.; Xu, Y.; Zhang, X.; Fan, X. Chem. Commun. 2016, 52, 10529.
[9] Lu, Y.; Wang, D. -H.; Engle, K. M.; Yu, J. -Q. J. Am. Chem. Soc. 2010, 132, 5916.
[10] Wang, X.; Lu, Y.; Dai, H. -X.; Yu, J. -Q. J. Am. Chem. Soc. 2010, 132, 12203.
[11] Huang, C.; Chattopadhyay, B.; Gevorgyan, V. J. Am. Chem. Soc. 2011, 133, 12406.
[12] Mei, T. -S.; Giri, R.; Maugel, N.; Yu, J. -Q. Angew. Chem., Int. Ed. 2008, 47, 5215.
[13] Giri, R.; Maugel, N.; Li, J. -J.; Wang, D. -H.; Breazzano, S. P.; Saunders, L. B.; Yu, J. -Q. J. Am. Chem. Soc. 2007, 129, 3510.
[14] Wang, D. -H.; Engle, K. M.; Yu, B. -F.; Yu, J. -Q. Science 2010, 327, 315.
[15] Giri, R.; Lam, J. K.; Yu, J. -Q. J. Am. Chem. Soc. 2010, 132, 686.
[16] Xiao, B.; Fu, Y.; Xu, J.; Gong, T. -J.; Dai, J. -J.; Yi, J.; Liu, L. J. Am. Chem. Soc. 2010, 132, 468.
[17] Duong, H. A.; Gilligan, R. E.; Cooke, M. L.; Phipps, R. J.; Gaunt, M. J. Angew. Chem., Int. Ed. 2011, 50, 463.
[18] Xiao, B.; Gong, T. -J.; Xu, J.; Liu, Z. -J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 1466.
[19] Santhoshkumar, R.; Mannathan, S.; Cheng, C. -H. J. Am. Chem. Soc. 2015, 137, 16116.
[20] Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300.
[21] Chen, X.; Hao, X. -S.; Goodhue, C. E.; Yu, J. -Q. J. Am. Chem. Soc. 2006, 128, 6790.
[22] Pan, F.; Lei, Z.; Wang, H.; Li, H.; Sun, J.; Shi, Z. -J. Angew. Chem., Int. Ed. 2013, 52, 2063.
[23] Wang, S.; Hou, J. -T.; Feng, M. -L.; Zhang, X. -Z.; Chen, S. -Y.; Yu, X. -Q. Chem. Commun. 2016, 52, 2709.
[24] Wang, Z.; Tian, Q.; Yu, X.; Kuang, C. Adv. Synth. Catal. 2014, 5, 961.
[25] Gong, B.; Shi, J.; Wang, X.; Yan, Y.; Li, Q.; Meng, Y.; Xu, H. E.; Yi, W. Adv. Synth. Catal. 2014, 356, 137.
[26] Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.
[27] Feng, Y.; Chen, G. Angew. Chem., Int. Ed. 2010, 49, 958.
[28] Gutekunst, W. R.; Gianatassio, R.; Baran, P. S. Angew. Chem., Int. Ed. 2012, 51, 7507.
[29] Aihara,Y.; Chatani, N. Chem. Sci. 2013, 4, 664.
[30] Rouqueta, G.; Chatani, N. Chem. Sci. 2013, 4, 2201.
[31] Suess, A. M.; Ertem, M. Z.; Cramer, C. J.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 9797.
[32] Wang, S.; Guo, R.; Wang, G.; Chen, S. -Y.; Yu, X. -Q. Chem. Commun. 2014, 50, 12718.
[33] Matsubara, T.; Asako, S.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2014, 136, 646.
[34] Ilies, L.; Ichikawa, S.; Asako, S.; Matsubara, T.; Nakamura. E. Adv. Synth. Catal. 2015, 357, 2175.
[35] Aihara, Y.; Chatani, N. J. Am. Chem. Soc. 2013, 135, 5308.
[36] Grigorjeva, L.; Daugulis, O. Angew. Chem., Int. Ed. 2014, 53, 10209.
[37] Wu, X.; Yang, K.; Zhao, Y.; Sun, H.; Li, G.; Ge, H. Nat. Commun. 2015, 6, 6462.
[38] Tran, L. D.; Daugulis, O. Angew. Chem., Int. Ed. 2012, 51, 5278.
[39] Shang, M.; Sun, S. -Z.; Dai, H. -X.; Yu, J. -Q. J. Am. Chem. Soc. 2014, 136, 3354.
[40] Huang, X.; Huang, J.; Du, C.; Zhang, X.; Song, F.; You, J. Angew. Chem., Int. Ed. 2013, 52, 12970.
[41] Zhang, L. -B.; Hao, X. -Q.; Zhang, S. -K.; Liu, Z. -J.; Zheng, X. -X.; Gong, J. -F.; Niu, J. -L.; Song, M. F. Angew. Chem., Int. Ed. 2015, 54, 272.
[42] Lee, P. -S.; Fujita, T.; Yoshikai, N. J. Am. Chem. Soc. 2011, 133, 17283.
[43] Inamoto, K.; Saito, T.; Katsuno, M.; Sakamoto, T.; Hiroya, K. Org. Lett. 2007, 15, 2931.
[44] Hafner, D. -C. A.; Bräse, S. Angew. Chem., Int. Ed. 2012, 51, 3713.
[45] Cai, G.; Fu, Y.; Li, Y.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 7666.
[46] Shao, J.; Chen, W.; Giulianotti, M. A.; Houghten, R. A.; Yu, Y. Org. Lett. 2012, 14, 5452.
[47] Leow, D.; Li, G.; Mei, T. -S.; Yu, J. -Q. Nature 2012, 486, 518.
[48] Tang, R. -Y.; Li, G.; Yu, J. -Q. Nature 2014, 507, 215.
[49] Wan, L.; Dastbaravardeh, N.; Li, G.; Yu, J. -Q. J. Am. Chem. Soc. 2013, 135, 18056.
[50] Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965.
[51] Tran, L. D.; Daugulis, O. Angew. Chem., Int. Ed. 2012, 51, 5188.
[52] Dai, H. -X.; Stepan, A. F.; Plummer, M. S.; Zhang, Y. H.; Yu, J. -Q. J. Am. Chem. Soc. 2011, 133, 7222.
[53] Wang, B.; Shen, C.; Yao, J.; Yin, H.; Zhang, Y. Org. Lett. 2014, 16, 46.
[54] Baba, K.; Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11892.
[55] Zhang, H.; Hu, R. -B.; Zhang, X. -Y.; Li, S. -X.; Yang, S. -D. Chem. Commun. 2014, 50, 4686.
[56] Chary, B. C.; Kim, S.; Park, Y.; Kim, J.; Lee, P. H. Org. Lett. 2013, 15, 2692.
[57] Chan, L. Y.; Cheong, L.; Kim, S. Org. Lett. 2013, 15, 2186.
[58] Yang, J.; Fu, T.; Long, Y.; Zhou, X. Chin. J. Org. Chem. 2017, 37, 1111(in Chinese). (杨军, 付婷, 龙洋, 周向葛, 有机化学, 2017, 37, 1111.)

Outlines

/