Issue 51, 2021

Z-Selective Pd-catalyzed 2,2,2-trifluoroethylation of acrylamides at room temperature

Abstract

A straightforward 2,2,2-trifluoroethylation of acrylamides by Pd-catalyzed C–H bond activation was reported by using a fluorinated hypervalent iodine reagent as a coupling partner. At room temperature, this additive-free approach allowed the synthesis of Z-2,2,2-trifluoroethylated acrylamides (19 examples, up to 73% yield) in a stereoselective manner. Under these mild reaction conditions, the methodology turned out to be functional group tolerant and mechanistic studies gave us a better understanding of the transformation.

Graphical abstract: Z-Selective Pd-catalyzed 2,2,2-trifluoroethylation of acrylamides at room temperature

Supplementary files

Article information

Article type
Communication
Submitted
15 apr 2021
Accepted
25 may 2021
First published
28 may 2021

Chem. Commun., 2021,57, 6241-6244

Z-Selective Pd-catalyzed 2,2,2-trifluoroethylation of acrylamides at room temperature

L. Ruyet, M. I. Lapuh, V. S. Koshti, T. Földesi, P. Jubault, T. Poisson, Z. Novák and T. Besset, Chem. Commun., 2021, 57, 6241 DOI: 10.1039/D1CC02007B

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