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

Song-Lin Zhang*, Jia-Jia Dong

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

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

DOI: 10.1021/acs.orglett.9b02516

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Abstract

An ammonium hydrogen-bonding-assisted α-F elimination from Cu-CF₃ compounds generates R₃N·HF reagents in situ. This strategy enables a dual fluorination and trifluoromethylation of terminal alkynes in the presence of a single Cu(III)-CF₃ compound and a tertiary amine with excellent regio- and stereoselectivity.

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syn-Fluoro- and -Oxy-trifluoromethylation of Arylacetylenes

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

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Key Words

fluorination, trifluoromethylation

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ID: J54-Y2019