Cascade cyclization/fluoromethylthiolation of alkynes, unsaturated α-bromocarbonyls and PhSO2SRF

Cui Zhang; Yun-Tao Shen; Ning-Xin Xia; Xin-Song Zhou; Li-Bo Yang; Jia Hu; Ya-Min Li

doi:10.1039/D5QO00585J

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Cascade cyclization/fluoromethylthiolation of alkynes, unsaturated α-bromocarbonyls and PhSO₂SR_F†

Cui Zhang,^a Yun-Tao Shen,^a Ning-Xin Xia,^a Xin-Song Zhou,^a Li-Bo Yang,^a Jia Hu^a and Ya-Min Li

*^a

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* Corresponding authors

^a Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P. R. China
E-mail: liym@kust.edu.cn

Abstract

A copper-catalyzed cyclization/fluoromethylthiolation cascade of alkynes, unsaturated α-bromocarbonyls and PhSO₂SCF₂H/PhSO₂SCF₃ has been developed to access fluoromethylthiolated cyclopentenes and cyclohexenes. The present reaction enables the construction of three new chemical bonds in a single step through the addition of alkyl radicals across alkynes, followed by cyclization and fluoromethylthiolation. It is characterized by high chemoselectivity and a broad substrate scope.

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Article information

DOI: https://doi.org/10.1039/D5QO00585J
Article type: Research Article
Submitted: 28 Mar 2025
Accepted: 13 May 2025
First published: 14 May 2025

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Org. Chem. Front., 2025, Advance Article

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Cascade cyclization/fluoromethylthiolation of alkynes, unsaturated α-bromocarbonyls and PhSO₂SR_F

C. Zhang, Y. Shen, N. Xia, X. Zhou, L. Yang, J. Hu and Y. Li, Org. Chem. Front., 2025, Advance Article , DOI: 10.1039/D5QO00585J

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