Visible light-induced one-pot synthesis of CF3/CF2-substituted cyclobutene derivatives

Xiao Hu; Aishun Ding; Dawen Xu; Hao Guo

doi:10.1039/D1CC02696H

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Visible light-induced one-pot synthesis of CF₃/CF₂-substituted cyclobutene derivatives†

Xiao Hu,^a Aishun Ding,

^a Dawen Xu*^ab and Hao Guo

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai 200438, P. R. China
E-mail: Hao_Guo@fudan.edu.cn

^b Zhuhai Fudan Innovation Institute, Hengqin New Area, Zhuhai, Guangdong 519000, P. R. China
E-mail: 13210220024@fudan.edu.cn

Abstract

An efficient one-pot approach for the controllable synthesis of trifluoromethyl/gem-difluoromethylene substituted cyclobutene derivatives has been developed. The mechanism may involve visible light-induced [2+2]-cycloaddition of quinolinones with 1-bromo-1-trifluoromethylethene, followed by base-promoted dehydrobromination, [1,3]-H shift and further dehydrofluorination. A variety of CF₃/CF₂-substituted cyclobutenes that are currently difficult to obtain are afforded in good yields in this protocol, which may find its way into future fluorinated cyclobutene preparation.

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Article information

DOI: https://doi.org/10.1039/D1CC02696H
Article type: Communication
Submitted: 22 May 2021
Accepted: 30 Jun 2021
First published: 30 Jun 2021

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Chem. Commun., 2021,57, 7441-7444

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Visible light-induced one-pot synthesis of CF₃/CF₂-substituted cyclobutene derivatives

X. Hu, A. Ding, D. Xu and H. Guo, Chem. Commun., 2021, 57, 7441 DOI: 10.1039/D1CC02696H

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