Copper(I)-Catalyzed Interrupted Click Reaction with TMSCF3 : Synthesis of 5-Trifluoromethyl 1,2,3-Triazoles

Organic Letters
Kelvin Pak Shing Cheung, Gavin Chit Tsui

Abstract

We herein describe a Cu(I)-catalyzed interrupted click reaction, using (trifluoromethyl)trimethylsilane (TMSCF3) as a nucleophilic CF3 source, to synthesize 5-trifluoromethyl 1,2,3-triazoles in one step from readily available terminal alkynes and azides. The reaction shows complete regioselectivity, broad substrate scope, and good functional group tolerability. The application of the reaction has been demonstrated in the synthesis of a trifluoromethylated analog of antiepileptic drug rufinamide.

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Citations

Nov 16, 2017·Chemical Communications : Chem Comm·Gwi-Rim ParkEun Jin Cho
Jul 13, 2019·Angewandte Chemie·Egor M Larin, Mark Lautens

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