Copper(ii)-catalyzed trifluoromethylation of iodoarenes using Chen's reagent?

Organic Chemistry Frontiers Pub Date: 2018-01-25 DOI: 10.1039/C8QO00025E

Abstract

The introduction of a trifluoromethyl group to organic molecules is significant for modern drug discovery; thus practical routes towards catalytic trifluoromethylation are highly desired. Herein, we report the efficient copper(II)-catalyzed nucleophilic trifluoromethylation of various aryl and heteroaryl iodides using methyl fluorosulfonyldifluoroacetate (FO2SCF2CO2Me, Chen's reagent). The use of CuCl2 instead of CuI resulted in a significant improvement in the original Chen's methodology; specifically, catalytic amounts (10 to 15%) of CuCl2 were used instead of Cu(I) salts for the generation of CuCF3 species. The improved trifluoromethylation converts aryl and heteroaryl iodides into the corresponding CF3-containing molecules with multiple functional groups in moderate to high yields. Moreover, a mechanism was proposed for this new catalytic system.

Graphical abstract: Copper(ii)-catalyzed trifluoromethylation of iodoarenes using Chen's reagent
Recommended Literature