Issue 14, 2022

Photocatalyst-, metal- and additive-free regioselective radical cascade sulfonylation/cyclization of benzimidazole derivatives with sulfonyl chlorides induced by visible light

Abstract

Herein, an environmentally friendly and practical protocol for the visible-light-triggered regioselective radical cascade sulfonylation/cyclization of unactivated alkenes towards the synthesis of polycyclic benzimidazoles containing the sulfone group has been developed. Notably, the control experiments demonstrated that a radical pathway was involved in this reaction, and a sulfonyl radical center was initially generated via self-homolysis of sulfonyl chloride upon irradiation. Moreover, this protocol features a wide substrate scope, high atom economy, and excellent regioselectivity, and is easy to scale up.

Graphical abstract: Photocatalyst-, metal- and additive-free regioselective radical cascade sulfonylation/cyclization of benzimidazole derivatives with sulfonyl chlorides induced by visible light

Supplementary files

Article information

Article type
Research Article
Submitted
06 Apr 2022
Accepted
22 May 2022
First published
24 May 2022

Org. Chem. Front., 2022,9, 3669-3676

Photocatalyst-, metal- and additive-free regioselective radical cascade sulfonylation/cyclization of benzimidazole derivatives with sulfonyl chlorides induced by visible light

B. Sun, H. Tian, Z. Ni, P. Huang, H. Ding, B. Li, C. Jin, C. Wu and R. Shen, Org. Chem. Front., 2022, 9, 3669 DOI: 10.1039/D2QO00518B

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