Photoredox β-thiol-α-carbonylation of enones accompanied by unexpected Csp2–C(CO) bond cleavage

Rui Ma; Jie Feng; Kuili Zhang; Beichen Zhang; Ding Du

doi:10.1039/D0OB01349H

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Photoredox β-thiol-α-carbonylation of enones accompanied by unexpected Csp²–C(CO) bond cleavage†

Rui Ma,^a Jie Feng,

^a Kuili Zhang,^a Beichen Zhang^a and Ding Du

*^a

Author affiliations

* Corresponding authors

^a State Key Laboratory of Natural Medicines, Department of Organic Chemistry, China Pharmaceutical University, No. 24 Tongjiaxiang Road, Nanjing, P.R. China
E-mail: ddmn9999@ cpu.edu.cn

Abstract

An olefinic difunctionalization method of enones was presented here via aerobic visible-light catalysis. A novel reactivity was showcased in conjunction with the selective Csp²–C(CO) bond activation of enones, which provided a convenient method for the preparation of various β-thiolated-α-functionalized compounds. Moreover, the preliminary investigation of the mechanism indicated that a β-peroxysulfide intermediate was formed under the promotion of visible light under an oxygen atmosphere, which finally induced the unexpected C–C bond cleavage.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/D0OB01349H
Article type: Communication
Submitted: 01 Jul 2020
Accepted: 15 Sep 2020
First published: 15 Sep 2020

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Org. Biomol. Chem., 2020,18, 7549-7553

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Photoredox β-thiol-α-carbonylation of enones accompanied by unexpected Csp²–C(CO) bond cleavage

R. Ma, J. Feng, K. Zhang, B. Zhang and D. Du, Org. Biomol. Chem., 2020, 18, 7549 DOI: 10.1039/D0OB01349H

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Organic & Biomolecular Chemistry