Exploiting the inductive effect of the trifluoromethyl group: regioselective gold-catalyzed hydration of 2,2,2-trifluoroethyl-substituted alkynes

Raphaël Gauthier; Nikolaos V Tzouras; Steven P Nolan; Jean-François Paquin

doi:10.1039/d3cc02034g

Exploiting the inductive effect of the trifluoromethyl group: regioselective gold-catalyzed hydration of 2,2,2-trifluoroethyl-substituted alkynes

Chem Commun (Camb). 2023 Jul 20;59(59):9138-9141. doi: 10.1039/d3cc02034g.

Authors

Raphaël Gauthier¹, Nikolaos V Tzouras², Steven P Nolan², Jean-François Paquin¹

Affiliations

¹ PROTEO, CCVC, Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC, G1V 0A6, Canada. jean-francois.paquin@chm.ulaval.ca.
² Department of Chemistry and Centre for Sustainable Chemistry, Ghent University, Krijgslaan 281, S-3, Ghent 9000, Belgium.

PMID: 37409523
DOI: 10.1039/d3cc02034g

Abstract

The gold-catalyzed hydration of 2,2,2-trifluoroethyl-substituted alkynes is highly regioselective, producing β-trifluoromethylketones as major products. This transformation illustrates the strong directing effect of the trifluoromethyl group, through its inductive effect, in gold-catalyzed addition to alkynes.