Issue 38, 2022

Straightforward synthesis of bench-stable heteroatom-centered difluoromethylated entities via controlled nucleophilic transfer from activated TMSCHF2

Abstract

The commercially available and experimentally convenient (bp 65 °C) difluoromethyltrimethylsilane (TMSCHF2) is proposed as a valuable difluoromethylating transfer reagent for delivering the CHF2 moiety to various heteroatom-based electrophiles. Upon activation with an alkoxide, a conceptually intuitive nucleophilic displacement directly furnishes in high yields the bench-stable analogues.

Graphical abstract: Straightforward synthesis of bench-stable heteroatom-centered difluoromethylated entities via controlled nucleophilic transfer from activated TMSCHF2

Supplementary files

Article information

Article type
Communication
Submitted
12 Feb 2022
Accepted
05 Apr 2022
First published
05 Apr 2022
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2022,58, 5761-5764

Straightforward synthesis of bench-stable heteroatom-centered difluoromethylated entities via controlled nucleophilic transfer from activated TMSCHF2

M. Miele, L. Castoldi, X. Simeone, W. Holzer and V. Pace, Chem. Commun., 2022, 58, 5761 DOI: 10.1039/D2CC00886F

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