Photochemically induced chloromethylation/cyclization of benzimidazole derivatives with CCl4/CHCl3

Yanmin Liu; Ziwei Li; Luyao Yang; Shuo Li; Zhiwei Chen

doi:10.1039/D3OB01290E

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Photochemically induced chloromethylation/cyclization of benzimidazole derivatives with CCl₄/CHCl₃†

Yanmin Liu,^a Ziwei Li,^a Luyao Yang,^a Shuo Li

^a and Zhiwei Chen

*^a

Author affiliations

* Corresponding authors

^a Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology; College of Pharmaceutical Sciences, Zhejiang University of Technology, Chao Wang Road 18th, 310014 Hangzhou, China
E-mail: chenzhiwei@zjut.edu.cn

Abstract

Herein, it is reported that a series of trichloromethyl/dichloromethyl substituted benzimidazole derivatives have been synthesized by dechlorination of CCl₄/CHCl₃ to form polychloromethyl radicals and cyclization with an unactivated olefin under a purple LED lamp. The protocol features a wide substrate scope, high atom economy, and excellent regioselectivity, and is easy to scale up.

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Article information

DOI: https://doi.org/10.1039/D3OB01290E
Article type: Paper
Submitted: 14 Aug 2023
Accepted: 09 Oct 2023
First published: 11 Oct 2023

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Org. Biomol. Chem., 2023,21, 8690-8694

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Photochemically induced chloromethylation/cyclization of benzimidazole derivatives with CCl₄/CHCl₃

Y. Liu, Z. Li, L. Yang, S. Li and Z. Chen, Org. Biomol. Chem., 2023, 21, 8690 DOI: 10.1039/D3OB01290E

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Organic & Biomolecular Chemistry