syn-Fluoro- and -Oxy-trifluoromethylation of Arylacetylenes

Song-Lin Zhang*, Hai-Xing Wan and Wen-Feng Bie

*Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu 214122, China, Email: slzhangjiangnan.edu.cn

S.-L. Zhang, H.-X. Wan, W.-F. Bie, Org. Lett., 2017, 19, 6372-6375.

DOI: 10.1021/acs.orglett.7b03229

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Abstract

The collaboration of (phen)Cu^III(CF₃)₃ and CsF enables a one-step concurrent fluoro-trifluoromethylation across the triple bond of arylacetylenes in a syn mode to provide chemo-, regio-, and stereoselectively (Z)-α-fluoro-β-CF₃ styrenes. This method can be extended to achieve syn-oxy-trifluoromethylation and syn-aryl-trifluoromethylation.

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proposed mechanism

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Hydrogen-Bonding-Assisted α-F Elimination from Cu-CF₃ for in Situ Generation of R₃N·HF Reagents: Reaction Design and Applications

S.-L. Zhang, J.-J. Dong, Org. Lett., 2019, 21, 6893-6896.

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Key Words

fluorination, trifluoromethylation

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ID: J54-Y2017