Photoinduced Copper-Catalyzed Monofluoroalkylation of Terminal Alkynes to Propargylic Fluorides

Duo-Duo Hu, Chao Li, Qian Gao, Tian-Mei Nie, Kai-Fan Zhang, Bing-Bing Wu, Yan Li* and Xi-Sheng Wang*

*Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China, Email: liyannsdfmu.edu.cn, xswang77ustc.edu.cn

D.-D. Hu, C. Li, Q. Gao, T.-M. Nie, K.-F. Zhang, B.-B. Wu, Y. Li, X.-S. Wang, Org. Lett., 2023, 25, 4514-4519.

DOI: 10.1021/acs.orglett.3c01531

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Abstract

A photoinduced copper-catalyzed monofluoroalkylation of alkynes with readily available monofluoroalkyl triflates provides valuable propargyl fluorides in good yields under mild conditions. This C-C bond formation avoids the use of highly toxic fluorination reagents. Preliminary mechanistic studies reveal that a ligand-matched alkynyl copper complex might be the key photoactive substance.

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proposed mechanism

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Key Words

propargyl fluorides. alkynylation, photochemistry

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ID: J54-Y2023