Straightforward synthesis of bench-stable heteroatom-centered difluoromethylated entities via controlled nucleophilic transfer from activated TMSCHF 2

Margherita Miele; Laura Castoldi; Xenia Simeone; Wolfgang Holzer; Vittorio Pace

doi:10.1039/d2cc00886f

Straightforward synthesis of bench-stable heteroatom-centered difluoromethylated entities via controlled nucleophilic transfer from activated TMSCHF 2

Margherita Miele
, Laura Castoldi
, Xenia Simeone
, Wolfgang Holzer
, Vittorio Pace (Korresp. Autor*in)

Department für Pharmazeutische Wissenschaften

Veröffentlichungen: Beitrag in Fachzeitschrift › Artikel › Peer Reviewed

Abstract

The commercially available and experimentally convenient (bp 65 °C) difluoromethyltrimethylsilane (TMSCHF 2) is proposed as a valuable difluoromethylating transfer reagent for delivering the CHF 2 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.

Originalsprache	Englisch
Seiten (von - bis)	5761-5764
Seitenumfang	4
Fachzeitschrift	Chemical Communications
Jahrgang	58
Ausgabenummer	38
DOIs	https://doi.org/10.1039/d2cc00886f
Publikationsstatus	Veröffentlicht - 2022

Fördermittel

The authors thank the University of Vienna, the University of Torino and FWF (project P33130) for financial support.

ÖFOS 2012

104015 Organische Chemie

Schlagwörter

Difluoromethylation
Nucleophilic displacement

Zugriff auf Dokument

10.1039/d2cc00886fLizenz: CC BY-NC 3.0

https://phaidra.univie.ac.at/o:1632830Lizenz: CC BY-NC 3.0

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abstract = "The commercially available and experimentally convenient (bp 65 °C) difluoromethyltrimethylsilane (TMSCHF 2) is proposed as a valuable difluoromethylating transfer reagent for delivering the CHF 2 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. ",

keywords = "Indicators and Reagents, Difluoromethylation, Nucleophilic displacement",

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AU - Holzer, Wolfgang

AU - Pace, Vittorio

PY - 2022

Y1 - 2022

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AB - The commercially available and experimentally convenient (bp 65 °C) difluoromethyltrimethylsilane (TMSCHF 2) is proposed as a valuable difluoromethylating transfer reagent for delivering the CHF 2 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.

KW - Indicators and Reagents

KW - Difluoromethylation

KW - Nucleophilic displacement

UR - https://www.scopus.com/pages/publications/85129667799

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DO - 10.1039/d2cc00886f

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EP - 5764

JO - Chemical Communications

JF - Chemical Communications

IS - 38

ER -

Straightforward synthesis of bench-stable heteroatom-centered difluoromethylated entities via controlled nucleophilic transfer from activated TMSCHF 2

Abstract

Fördermittel

ÖFOS 2012

Schlagwörter

Zugriff auf Dokument

Andere Dateien und Links

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