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

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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

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Publication details

The article was received on 05 Sep 2019, accepted on 03 Oct 2019 and first published on 11 Oct 2019


Article type: Communication
DOI: 10.1039/C9CC06929A
Chem. Commun., 2019, Advance Article
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    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, Advance Article , DOI: 10.1039/C9CC06929A

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