Difluorocarbene-MediatedTrimethylsilylation of Nucleophileswith HCF<sub>2</sub>N(TMS)<sub>2</sub> as a Silylation Reagent

Described herein is the trimethylsilylation of various nucleophiles using a combination of HCF<sub>3</sub> and NaHMDS. This facile protocol enables the rapid construction of alkynylsilanes, silyl enol ethers, etc., under mild conditions. Detailed mechanistic studies indicate that the trimethylsilicon intermediate formed <i>in situ</i> can be readily attacked by nucleophiles, with the activation of the base NaHMDS by difluorocarbene. This work first utilizes the structure of HMDS as a silicon source in the trimethylsilylation of terminal alkynes.

Publication Details

Journal
Figshare
Published
2025-02-10
DOI
https://doi.org/10.1021/acs.orglett.5c00227.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Difluorocarbene-MediatedTrimethylsilylation of Nucleophileswith HCF2N(TMS)2 as a Silylation Reagent

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Fluorine in Organic Chemistry
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Difluorocarbene-MediatedTrimethylsilylation of Nucleophileswith HCF2N(TMS)2 as a Silylation Reagent

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Abstract

Described herein is the trimethylsilylation of various nucleophiles using a combination of HCF<sub>3</sub> and NaHMDS. This facile protocol enables the rapid construction of alkynylsilanes, silyl enol ethers, etc., under mild conditions. Detailed mechanistic studies indicate that the trimethylsilicon intermediate formed <i>in situ</i> can be readily attacked by nucleophiles, with the activation of the base NaHMDS by difluorocarbene. This work first utilizes the structure of HMDS as a silicon source in the trimethylsilylation of terminal alkynes.

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Fluorine in Organic Chemistry
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Difluorocarbene-MediatedTrimethylsilylation of Nucleophileswith HCF<sub>2</sub>N(TMS)<sub>2</sub> as a Silylation Reagent · Figshare (2025) | TGRS Research Map | TGRS