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DOI: 10.1055/a-1995-6124
Photoredox-Catalysis-Enabled Ring-Opening Functionalization of Aryl Cyclopropanes
We gratefully acknowledge funding by the National Natural Science Foundation of China (21871138, 22271151), the Natural Science Foundation of Jiangsu Province (BK20220327), and the Distinguished Youth Foundation of Jiangsu Province.
Abstract
Cyclopropanes have long been recognized as privileged synthons in organic synthesis, providing access to 1,3-difunctionalized scaffolds. However, the synthetic potential of aryl cyclopropanes, one of the most important subclasses of cyclopropanes, is far less explored. Recently, we uncovered a visible-light-promoted strategy for the ring-opening functionalization of a series of aryl cyclopropanes through open-shell intermediates. By leveraging the activation of an aryl radical cation derived from an oxidative single-electron transfer, the C–C bond of the cyclopropane is weakened and cleaves upon a regio- and stereoselective nucleophilic attack with an exogenous nucleophile to provide a benzyl radical that can be readily elaborated to diverse functionalities.
1 Introduction
2 Core Concept of Our Design
3 Photoredox-Catalyzed Oxoamination of Aryl Cyclopropanes
4 Photoredox-Catalyzed Hydroheterofunctionalization of Aryl Cyclopropanes
5 Photoredox-Catalyzed Fluoroallylation of gem-Difluorocyclopropanes
6 Conclusion
Key words
arylcyclopropanes - photoredox catalysis - single-electron transfer - radical cation - SN2 reactionPublication History
Received: 16 November 2022
Accepted after revision: 09 December 2022
Accepted Manuscript online:
09 December 2022
Article published online:
05 January 2023
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References
- 1a Schneider TF, Kaschel J, Werz DB. Angew. Chem. Int. Ed. 2014; 53: 5504
- 1b Grover HK, Emmett MR, Kerr MA. Org. Biomol. Chem. 2015; 13: 655
- 1c Singh P, Varshnaya RK, Dey R, Banerjee P. Adv. Synth. Catal. 2020; 362: 1447
- 2 Taily IM, Saha D, Banerjee P. Org. Biomol. Chem. 2021; 19: 8627
- 3a Ouellette RJ, Shaw DL, South AJr. J. Am. Chem. Soc. 1964; 86: 2744
- 3b Ouellette RJ, Shaw DL. J. Am. Chem. Soc. 1964; 86: 1651
- 3c Ouellette RJ, Robins RD, South AJr. J. Am. Chem. Soc. 1968; 90: 1619
- 4a Gieuw MH, Leung VM.-Y, Ke Z, Yeung Y.-Y. Adv. Synth. Catal. 2018; 360: 4306
- 4b Banik SM, Mennie KM, Jacobsen EN. J. Am. Chem. Soc. 2017; 139: 9152
- 4c Kuboki Y, Arisawa M, Murai K. RSC Adv. 2020; 10: 37797
- 5 Rao VR, Hixson SS. J. Am. Chem. Soc. 1979; 101: 6458
- 6a Pitts CR, Ling B, Snyder JA, Bragg AE, Lectka T. J. Am. Chem. Soc. 2016; 138: 6598
- 6b Peng P, Yan X, Zhang K, Liu Z, Zeng L, Chen Y, Zhang H, Lei A. Nat. Commun. 2021; 12: 3075
- 7 Lu Z, Parrish JD, Yoon TP. Tetrahedron 2014; 70: 4270
- 8a Li X, Shui Y, Shen P, Wang Y.-P, Zhang C, Feng C. Chem 2022; 8: 2245
- 8b Tang H.-J, Zhang X, Zhang Y.-F, Feng C. Angew. Chem. Int. Ed. 2020; 59: 5242
- 8c Liu H, Ge L, Wang D.-X, Chen N, Feng C. Angew. Chem. Int. Ed. 2019; 58: 3918
- 8d Zhang Y, Liu H, Tang L, Tang H.-J, Wang L, Zhu C, Feng C. J. Am. Chem. Soc. 2018; 140: 10695
- 9 Ge L, Wang D.-X, Xing R, Ma D, Walsh PJ, Feng C. Nat. Commun. 2019; 10: 4367
- 10a Zuo Z, Daniliuc CG, Studer A. Angew. Chem. Int. Ed. 2021; 60: 25252
- 10b Zuo Z, Studer A. Org. Lett. 2022; 24: 949
- 11 Ge L, Zhang C, Pan C, Wang D.-X, Liu D.-Y, Li Z.-Q, Shen P, Tian L, Feng C. Nat. Commun. 2022; 13: 5938
- 12a Zhu C, Sun M.-M, Chen K, Liu H, Feng C. Angew. Chem. Int. Ed. 2021; 60: 20237
- 12b Zhu C, Liu Z.-Y, Tang L, Zhang H, Zhang Y.-F, Walsh PJ, Feng C. Nat.Commun. 2020; 11: 4860
- 12c Wang C.-Q, Ye L, Feng C, Loh T.-P. J. Am. Chem. Soc. 2017; 139: 1762
- 12d Wang C.-Q, Zhang Y, Feng C. Angew. Chem. Int. Ed. 2017; 56: 14918
- 12e Tian P, Wang C.-Q, Cai S.-H, Song S, Ye L, Feng C, Loh T.-P. J. Am. Chem. Soc. 2016; 138: 15869
- 13 Liu H, Li Y, Wang D.-X, Sun M.-M, Feng C. Org. Lett. 2020; 22: 8681