Issue 7, 2018

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
10 jan 2018
Accepted
24 jan 2018
First published
25 jan 2018

Org. Chem. Front., 2018,5, 1143-1147

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

S. Zhao, Y. Guo, E. Han, J. Luo, H. Liu, C. Liu, W. Xie, W. Zhang and M. Wang, Org. Chem. Front., 2018, 5, 1143 DOI: 10.1039/C8QO00025E

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