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

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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

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Publication details

The article was received on 10 Jan 2018, accepted on 24 Jan 2018 and first published on 25 Jan 2018


Article type: Research Article
DOI: 10.1039/C8QO00025E
Citation: Org. Chem. Front., 2018, Advance Article
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    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, Advance Article , DOI: 10.1039/C8QO00025E

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