REVIEWS

Advances in Selective Allylic C—H Amination of Internal Olefins

  • Yuan She ,
  • Shuyu Zhang ,
  • Le Wang
Expand
  • School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Received date: 2024-07-03

  Revised date: 2024-09-02

  Online published: 2024-10-11

Supported by

National Natural Science Foundation of China(22071149)

Abstract

In recent years, the allylic C—H amination of internal olefins has undergone rapid development. This reaction introduces nitrogen sources into the allylic positions of internal olefins via C—H activation efficiently to form new C—N bonds, thereby synthesizing nitrogen-containing compounds with significant biological activity and pharmaceutical potential. Given the relatively low reactivity of internal olefins and the challenges of chemoselectivity, regioselectivity and stereoselectivity during the reaction, the allylic C—H amination of internal olefins has been a great challenge for organic chemists. This review primarily covers the selective allylic C—H amination of internal olefins in recent years, categorizing the methods based on the mechanism of distinguishing different allylic C—H bonds to achieve selective amination, and summarizes the research progress in this field and its potential applications in synthesizing biologically active molecules.

Cite this article

Yuan She , Shuyu Zhang , Le Wang . Advances in Selective Allylic C—H Amination of Internal Olefins[J]. Chinese Journal of Organic Chemistry, 2025 , 45(2) : 531 -545 . DOI: 10.6023/cjoc202407007

References

[1]
Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257.
[2]
Brown, D. G.; Bostro?m, J. J. Med. Chem. 2016, 59, 4443.
[3]
Park, Y.; Kim, Y.; Chang, S. Chem. Rev. 2017, 117, 9247.
[4]
Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Acc. Chem. Res. 2008, 41, 40.
[5]
Trost, B. M.; Hansmann, M. M.; Thaisrivongs, D. A. Angew. Chem., Int. Ed. 2012, 51, 4950.
[6]
Davies, H. M. L.; Mortona, D. Chem. Soc. Rev. 2011, 40, 1857.
[7]
Cernak, T.; Dykstra, K. D.; Tyagarajan, S.; Vachalb, P.; Krskab, S. W. Chem. Soc. Rev. 2016, 45, 546.
[8]
Pàmies. O.; Margalef. J. S.; Judge. E.; Guiry. P. J.; Moberg. C.; Pericas. M. A. Chem. Rev. 2021, 121, 4373.
[9]
Burman, J. S.; Harris, R. J.; Farr, C. M. B.; Bacsa, J.; Blakey, S. B. ACS Catal. 2019, 9, 5474.
[10]
Bayeh, L.; Tambar, U. K. ACS Catal. 2017, 7, 8533.
[11]
Bayeh, L.; Le, P.; Tambar, U. K. Nature 2017, 547, 196.
[12]
Knecht, T.; Mondal, S.; Ye, J.-H.; Das, M.; Glorius, F. Angew. Chem., Int. Ed. 2019, 58, 7117.
[13]
Farr, C. M. B.; Kazerouni, A. M.; Park, B.; Poff, C. D.; Won, J.; Sharp, K. R.; Baik, M. H.; Blakey, S. B. J. Am. Chem. Soc. 2020, 142, 13996.
[14]
Lei, H.; Rovis, T. Nat. Chem. 2020, 12, 725.
[15]
Maloney, T. P.; Berman, J. L.; Michael, F. E. Angew. Chem., Int. Ed. 2022, 61, e202210109.
[16]
Lin, S.; Liu, Y.; Gao, K.-Y.; Chen, Z.-H.; Qian, J.; Liu, X.-B.; Li, Q.; Wang, H. ACS Catal. 2024, 14, 8865.
[17]
Liu, Y.; Chen, Z.-H.; Li, Y.; Qian, J.; Li, Q.-J.; Wang, H.-G. J. Am. Chem. Soc. 2022, 144, 14380.
[18]
Wang, L.; Wang, C.-L.; Li, Z.-H.; Lian, P.-F.; Kang, J.-C.; Zhou J.; Hao, Y.; Liu, R.-X.; Bai, H.-Y.; Zhang, S.-Y. Nat. Commun. 2024, 15, 1483.
[19]
Ide, T.; Feng, K.; Dixon, C. F.; Teng, D.; Clark, J. R.; Han, W.; Wendell, C. I.; Koch, V.; White, M. C. J. Am. Chem. Soc. 2021, 143, 14969.
[20]
Yang, B.; Liu, X.; Yu, A.; Yang, Q.; Wang, Y. ACS Catal. 2022, 12, 13411.
[21]
Cheung, K. P. S.; Fang, J.; Mukherjee, K.; Mihranyan, A.; Gevorgyan, V. Science 2022, 378, 1207.
Outlines

/