Active Trifluoromethylating Agents from Well-Defined Copper(I)−CF<SUB>3</SUB> Complexes

J. Am. Chem. Soc., 130 (27), 8600–8601, 2008. 10.1021/ja802946s
Web Release Date: June 11, 2008

Active Trifluoromethylating Agents from Well-Defined Copper(I)−CF₃ Complexes

Galyna G. Dubinina,^† Hideki Furutachi,^‡ and David A. Vicic^*^†

Department of Chemistry, University of Hawaii, 2545 McCarthy Mall, Honolulu, Hawaii 96822, and the Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University Kakuma-machi, Kanazawa 920−1192, Japan

vicic@hawaii.edu

Received April 28, 2008

Abstract:

The first examples of isolable and structurally characterized Cu(I)−CF₃ complexes are reported. N-Heterocyclic carbene (NHC)-supported copper tert-butoxide complexes reacted with Me₃Si−CF₃ to afford new (NHC)Cu−CF₃ complexes whose structures were dependent on whether or not the C₄−C₅ positions of the five-membered NHC rings were saturated. In situ generated (SIiPr)Cu−CF₃ cleanly transferred its trifluoromethyl group to a number of organic halides under mild conditions.

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