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Cu(III)-CF3 Complex Enabled Unusual (Z)-Selective Hydro-trifluoromethylation of Terminal Alkynes

Song-Lin Zhang*, Chang Xiao

*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, C. Xiao, J. Org. Chem., 2018, 83, 10908-10915.

DOI: 10.1021/acs.joc.8b01586 (free Supporting Information)


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Abstract

The use of a Cu(III)-CF3 reagent and a silane enables an efficient and selective hydro-trifluoromethylation of terminal alkynes in DMF to provide 1,2-disubstituted trifluoromethylated Z-alkenes. The unusual Z-selectivity and the compatibility of various functional groups make this reaction complementary to previously reported methods producing predominantly E-products.

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Key Words

trifluoromethyl alkenes, TES


ID: J42-Y2018