Issue 59, 2023
From the journal:

Chemical Communications

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

Raphaël Gauthier,a   Nikolaos V. Tzouras, ORCID logo b   Steven P. Nolan ORCID logo b  and  Jean-François Paquin ORCID logo *a  

* Corresponding authors

a PROTEO, CCVC, Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC, Canada
E-mail: jean-francois.paquin@chm.ulaval.ca

b Department of Chemistry and Centre for Sustainable Chemistry, Ghent University, Krijgslaan 281, S-3, Ghent 9000, Belgium

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.

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

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Article information

DOI
https://doi.org/10.1039/D3CC02034G
Article type
Communication
Submitted
26 Apr 2023
Accepted
28 Jun 2023
First published
06 Jul 2023

Chem. Commun., 2023,59, 9138-9141

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

R. Gauthier, N. V. Tzouras, S. P. Nolan and J. Paquin, Chem. Commun., 2023, 59, 9138 DOI: 10.1039/D3CC02034G

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