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

doi:10.6023/cjoc202406049

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.

Key words: C—H bond, internal alkene, hydroarylation, asymmetric catalysis, benzylic chiral center

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.

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Fig. & Tab. 15

Scheme 1. Early Murai type reactions

Scheme 2. Early exploration of asymmetric hydroarylation of strained olefins

Scheme 3. Asymmetric hydroarylation reaction of strained olefins catalyzed by iridium

Scheme 4. Asymmetric hydroarylation reaction of strained olefins with diverse arenes

Scheme 5. Iridium catalyzed asymmetric addition reaction of heterocyclic compounds to strained olefins

Scheme 6. Asymmetric hydroarylation reaction of strained olefins catalyzed by nickel

Scheme 7. Asymmetric hydroarylation of alkenyl ethers catalyzed by iridium

Scheme 8. Asymmetric hydroarylation reaction of alkenyl ethers with diverse arenes

Scheme 9. Iridium catalyzed asymmetric addition reaction of heterocyclic compounds to enamides

Scheme 10. Asymmetric hydroarylation of α,β-unsaturated carbonyl compounds catalyzed by iridium

Scheme 11. Asymmetric hydroarylation of α,β-unsaturated carbonyl compounds through counter-anion strategy

Scheme 12. Asymmetric hydroarylation of maleimide catalyzed by cobalt

Scheme 13. Asymmetric hydroarylation of maleimide catalyzed by rhodium

Scheme 14. Asymmetric hydroarylation of nitroalkenes catalyzed by rhodium

Scheme 15. Asymmetric hydroarylation of styrene catalyzed by nickel

References 28

[1]	(a) Achar, T. K.; Maiti, S.; Jana, S.; Maiti, D. ACS Catal. 2020, 10, 13748. pmid: 37163671
	(b) Dalton, T.; Faber, T.; Glorius, F. ACS Cent. Sci. 2021, 7, 245. pmid: 37163671
	(c) Dutta, U.; Maiti, S.; Bhattacharya, T.; Maiti, D. Science 2021, 372, eabd5992. pmid: 37163671
	(d) Lam, N. Y. S.; Wu, K.; Yu, J.-Q. Angew. Chem., Int. Ed. 2021, 60, 15767. pmid: 37163671
	(e) Li, Y.; Yuan, B.; Sun, Z.; Zhang, W. Green Synth. Catal. 2021, 2, 267. pmid: 37163671
	(f) Liu, B.; Romine, A. M.; Rubel, C. Z.; Engle, K. M.; Shi, B.-F. Chem. Rev. 2021, 121, 14957. pmid: 37163671
	(g) Zhang, J.; Lu, X.; Shen, C.; Xu, L.; Ding, L.; Zhong, G. Chem. Soc. Rev. 2021, 50, 3263. doi: 10.1039/d0cs00447b pmid: 37163671
	(h) He, Y.; Huang, Z.; Wu, K.; Ma, J.; Zhou, Y.-G.; Yu, Z. Chem. Soc. Rev. 2022, 51, 2759. pmid: 37163671
	(i) Sinha, S. K.; Guin, S.; Maiti, S.; Biswas, J. P.; Porey, S.; Maiti, D. Chem. Rev. 2022, 122, 5682. pmid: 37163671
	(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. doi: 10.1021/acs.chemrev.2c00888 pmid: 37163671
[2]	(a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
	(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. doi: 10.1021/jacs.8b04627 pmid: 30024748
	(b) Lee, P.-S.; Yoshikai, N. Org. Lett. 2015, 17, 22. pmid: 30024748
	(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. pmid: 30024748
	(d) Loup, J.; Zell, D.; Oliveira, J. C. A.; Keil, H.; Stalke, D.; Ackermann, L. Angew. Chem., Int. Ed. 2017, 56, 14197. pmid: 30024748
	(e) Pesciaioli, F.; Dhawa, U.; Oliveira, J. C. A.; Yin, R.; John, M.; Ackermann, L. Angew. Chem., Int. Ed. 2018, 57, 15425. pmid: 30024748
	(f) Song, G.; O, W. W. N.; Hou, Z. J. Am. Chem. Soc. 2014, 136, 12209. pmid: 30024748
[5]	(a) Shen, D.; Zhang, W.-B.; Li, Z.; Shi, S.-L.; Xu, Y. Adv. Synth. Catal. 2020, 362, 1125.
	(b) Shibata, T.; Ryu, N.; Takano, H. Adv. Synth. Catal. 2015, 357, 1131.
	(c) Diesel, J.; Finogenova, A. M.; Cramer, N. J. Am. Chem. Soc. 2018, 140, 4489.
	(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.
	(e) Zhang, W.-B.; Yang, X.-T.; Ma, J.-B.; Su, Z.-M.; Shi, S.-L. J. Am. Chem. Soc. 2019, 141, 5628.
	(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. pmid: 29474067
	(b) Wang, H.; Bai, Z.; Jiao, T.; Deng, Z.; Tong, H.; He, G.; Peng, Q.; Chen, G. J. Am. Chem. Soc. 2018, 140, 3542. doi: 10.1021/jacs.8b00641 pmid: 29474067
[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. doi: 10.1021/acs.orglett.7b02950 pmid: 29048911
[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. doi: 10.1021/jacs.9b12858 pmid: 31923357
[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. doi: 10.1021/acs.joc.8b00377 pmid: 29437389
[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. doi: 10.1021/jacs.3c00095 pmid: 36917558
[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. doi: 10.1021/acscatal.6b03217 pmid: 28435749
[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.

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