Issue 86, 2019

Highly chemoselective difluoromethylative homologation of iso(thio)cyanates: expeditious access to unprecedented α,α-difluoro(thio)amides

Abstract

The new motif – α,α-difluoromethyl thioamide – has been assembled starting from isothiocyanate (as thioamide precursor) and a formal difluoromethyl-carbanion generated from commercially available TMSCHF2. Upon proper activation of this reagent with potassium tert-amylate, the high-yielding transfer of the difluorinated nucleophile takes place under high chemocontrol. Various sensitive functionalities (e.g. ester, nitrile, nitro, azido groups) can be accommodated across the isothiocyanate core, thus allowing a wide scope. The methodology is highly flexible and adaptable to prepare analogous α,α-difluoromethyl oxoamides by conveniently using isocyanates as the electrophilic building-blocks.

Graphical abstract: Highly chemoselective difluoromethylative homologation of iso(thio)cyanates: expeditious access to unprecedented α,α-difluoro(thio)amides

Supplementary files

Article information

Article type
Communication
Submitted
05 Sep 2019
Accepted
03 Oct 2019
First published
11 Oct 2019
This article is Open Access
Creative Commons BY license

Chem. Commun., 2019,55, 12960-12963

Highly chemoselective difluoromethylative homologation of iso(thio)cyanates: expeditious access to unprecedented α,α-difluoro(thio)amides

M. Miele, R. D’Orsi, V. Sridharan, W. Holzer and V. Pace, Chem. Commun., 2019, 55, 12960 DOI: 10.1039/C9CC06929A

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