Issue 43, 2023

Trifluoromethylarylation of alkenes using anilines

Abstract

Nitrogen containing compounds, such as anilines, are some of the most widespread and useful chemical species, although their high and unselective reactivity has prevented their incorporation into many interesting transformations, such as the functionalization of alkenes. Herein we report a method that allows the trifluoromethylarylation of alkenes using anilines, for the first time, with no need for additives, transition metals, photocatalysts or an excess of reagents. An in-depth mechanistic study reveals the key role of hexafluoroisopropanol (HFIP) as a unique solvent, establishing a hydrogen bonding network with aniline and trifluoromethyl reagent, that is responsible for the altered reactivity and exquisite selectivity. This work uncovers a new mode of reactivity that involves the use of abundant anilines as a non-prefunctionalized aromatic source and the simultaneous activation of trifluoromethyl hypervalent iodine reagent.

Graphical abstract: Trifluoromethylarylation of alkenes using anilines

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Article information

Article type
Edge Article
Submitted
26 7月 2023
Accepted
19 10月 2023
First published
27 10月 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 12083-12090

Trifluoromethylarylation of alkenes using anilines

C. Corral Suarez and I. Colomer, Chem. Sci., 2023, 14, 12083 DOI: 10.1039/D3SC03868H

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