REVIEWS

Recent Progress in Metal-Catalyzed Asymmetric Hydroarylation of Internal Alkenes Through C—H Cleavage

  • Enze Lin ,
  • Bijie Li
Expand
  • Center of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing 100084

Received date: 2024-06-29

  Revised date: 2024-09-09

  Online published: 2024-10-11

Supported by

National Natural Science Foundation of China(22371160)

Abstract

Abstract Catalytic asymmetric addition of aryl C—H bonds to alkenes is an effective method for constructing benzylic chiral centers, offering advantages such as readily available starting materials, high atom economy, and diverse product structures. The study of the addition of aryl C—H bonds to terminal alkenes began earlier and has made significant progress. In contrast, research on the asymmetric addition of aryl C—H bonds to internal alkenes has been relatively lagging behind. The recent advances in metal-catalyzed asymmetric addition of aryl C—H bonds to internal alkenes are reviewed.

Cite this article

Enze Lin , Bijie Li . Recent Progress in Metal-Catalyzed Asymmetric Hydroarylation of Internal Alkenes Through C—H Cleavage[J]. Chinese Journal of Organic Chemistry, 2025 , 45(2) : 546 -558 . DOI: 10.6023/cjoc202406049

References

[1]
(a) Achar, T. K.; Maiti, S.; Jana, S.; Maiti, D. ACS Catal. 2020, 10, 13748.
[1]
(b) Dalton, T.; Faber, T.; Glorius, F. ACS Cent. Sci. 2021, 7, 245.
[1]
(c) Dutta, U.; Maiti, S.; Bhattacharya, T.; Maiti, D. Science 2021, 372, eabd5992.
[1]
(d) Lam, N. Y. S.; Wu, K.; Yu, J.-Q. Angew. Chem., Int. Ed. 2021, 60, 15767.
[1]
(e) Li, Y.; Yuan, B.; Sun, Z.; Zhang, W. Green Synth. Catal. 2021, 2, 267.
[1]
(f) Liu, B.; Romine, A. M.; Rubel, C. Z.; Engle, K. M.; Shi, B.-F. Chem. Rev. 2021, 121, 14957.
[1]
(g) Zhang, J.; Lu, X.; Shen, C.; Xu, L.; Ding, L.; Zhong, G. Chem. Soc. Rev. 2021, 50, 3263.
[1]
(h) He, Y.; Huang, Z.; Wu, K.; Ma, J.; Zhou, Y.-G.; Yu, Z. Chem. Soc. Rev. 2022, 51, 2759.
[1]
(i) Sinha, S. K.; Guin, S.; Maiti, S.; Biswas, J. P.; Porey, S.; Maiti, D. Chem. Rev. 2022, 122, 5682.
[1]
(j) Docherty, J. H.; Lister, T. M.; McArthur, G.; Findlay, M. T.; Domingo-Legarda, P.; Kenyon, J.; Choudhary, S.; Larrosa, I. Chem. Rev. 2023, 123, 7692.
[2]
(a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
[2]
(b) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
[3]
Lewis, L. N.; Smith, J. F. J. Am. Chem. Soc. 1986, 108, 2728.
[4]
(a) Grélaud, S.; Cooper, P.; Feron, L. J.; Bower, J. F. J. Am. Chem. Soc. 2018, 140, 9351.
[4]
(b) Lee, P.-S.; Yoshikai, N. Org. Lett. 2015, 17, 22.
[4]
(c) Liu, Y.-H.; Xie, P.-P.; Liu, L.; Fan, J.; Zhang, Z.-Z.; Hong, X.; Shi, B.-F. J. Am. Chem. Soc. 2021, 143, 19112.
[4]
(d) Loup, J.; Zell, D.; Oliveira, J. C. A.; Keil, H.; Stalke, D.; Ackermann, L. Angew. Chem., Int. Ed. 2017, 56, 14197.
[4]
(e) Pesciaioli, F.; Dhawa, U.; Oliveira, J. C. A.; Yin, R.; John, M.; Ackermann, L. Angew. Chem., Int. Ed. 2018, 57, 15425.
[4]
(f) Song, G.; O, W. W. N.; Hou, Z. J. Am. Chem. Soc. 2014, 136, 12209.
[5]
(a) Shen, D.; Zhang, W.-B.; Li, Z.; Shi, S.-L.; Xu, Y. Adv. Synth. Catal. 2020, 362, 1125.
[5]
(b) Shibata, T.; Ryu, N.; Takano, H. Adv. Synth. Catal. 2015, 357, 1131.
[5]
(c) Diesel, J.; Finogenova, A. M.; Cramer, N. J. Am. Chem. Soc. 2018, 140, 4489.
[5]
(d) Wang, Y.-X.; Qi, S.-L.; Luan, Y.-X.; Han, X.-W.; Wang, S.; Chen, H.; Ye, M. J. Am. Chem. Soc. 2018, 140, 5360.
[5]
(e) Zhang, W.-B.; Yang, X.-T.; Ma, J.-B.; Su, Z.-M.; Shi, S.-L. J. Am. Chem. Soc. 2019, 141, 5628.
[5]
(f) Harada, H.; Thalji, R. K.; Bergman, R. G.; Ellman, J. A. J. Org. Chem. 2008, 73, 6772.
[6]
(a) Marcum, J. S.; Roberts, C. C.; Manan, R. S.; Cervarich, T. N.; Meek, S. J. J. Am. Chem. Soc. 2017, 139, 15580.
[6]
(b) Wang, H.; Bai, Z.; Jiao, T.; Deng, Z.; Tong, H.; He, G.; Peng, Q.; Chen, G. J. Am. Chem. Soc. 2018, 140, 3542.
[7]
Aufdenblatten, R.; Diezi, S.; Togni, A. Monatsh. Chem. 2000, 131, 1345.
[8]
Tsuchikama, K.; Kasagawa, M.; Hashimoto, Y.-K.; Endo, K.; Shibata, T. J. Org. Chem. 2008, 693, 3939.
[9]
Shirai, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2015, 54, 9894.
[10]
Nagamoto, M.; Fukuda, J.-I.; Hatano, M.; Yorimitsu, H.; Nishimura, T. Org. Lett. 2017, 19, 5952.
[11]
Romero-Arenas, A.; Hornillos, V.; Iglesias-Sigüenza, J.; Fernández, R.; López-Serrano, J.; Ros, A.; Lassaletta, J. M. J. Am. Chem. Soc. 2020, 142, 2628.
[12]
Sevov, C. S.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 2116.
[13]
Chen, M.; Montgomery, J. ACS Catal. 2022, 12, 11015.
[14]
Ebe, Y.; Nishimura, T. J. Am. Chem. Soc. 2015, 137, 5899.
[15]
Ebe, Y.; Onoda, M.; Nishimura, T.; Yorimitsu, H. Angew. Chem., Int. Ed. 2017, 56, 5607.
[16]
Zhang, M.; Hu, L.; Lang, Y.; Cao, Y.; Huang, G. J. Org. Chem. 2018, 83, 2937.
[17]
Hatano, M.; Ebe, Y.; Nishimura, T.; Yorimitsu, H. J. Am. Chem. Soc. 2016, 138, 4010.
[18]
Zhao, W.; Li, B.-J. J. Am. Chem. Soc. 2023, 145, 6861.
[19]
Shibata, T.; Michino, M.; Kurita, H.; Tahara, Y.-K.; Kanyiva, K. S. Chem.-Eur. J. 2017, 23, 88.
[20]
Shibata, T.; Kurita, H.; Onoda, S.; Kanyiva, K. S. Asian J. Org. Chem. 2018, 7, 1411.
[21]
Shibata, T.; Sasaki, M.; Kojima, M.; Ito, M. Org. Lett. 2021, 23, 9078.
[22]
Satake, S.; Kurihara, T.; Nishikawa, K.; Mochizuki, T.; Hatano, M.; Ishihara, K.; Yoshino, T.; Matsunaga, S. Nat. Catal. 2018, 1, 585.
[23]
Kurihara, T.; Kojima, M.; Yoshino, T.; Matsunaga, S. Asian J. Org. Chem. 2020, 9, 368.
[24]
Wang, J.; Chen, H.; Kong, L.; Wang, F.; Lan, Y.; Li, X. ACS Catal. 2021, 11, 9151.
[25]
Potter, T. J.; Kamber, D. N.; Mercado, B. Q.; Ellman, J. A. ACS Catal. 2017, 7, 150.
[26]
Yang, H.; Zhang, R.; Zhang, S.-Z.; Gu, Q.; You, S.-L. ACS Catal. 2023, 13, 8838.
[27]
Ma, J.-B.; Zhao, X.; Zhang, D.; Shi, S.-L. J. Am. Chem. Soc. 2022, 144, 13643.
[28]
Wang, Z.-C.; Luo, X.; Zhang, J.-W.; Liu, C.-F.; Koh, M. J.; Shi, S.-L. Nat. Catal. 2023, 6, 1087.
Outlines

/

〈 〉