Difluorocarbene-Mediated Trimethylsilylation of Nucleophiles with HCF2N(TMS)2 as a Silylation Reagent

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-10 DOI:10.1021/acs.orglett.5c00227

Hao Ruan, Dong Zhu, Jingwei Zhao, Shifa Zhu

引用次数: 0

Abstract

Described herein is the trimethylsilylation of various nucleophiles using a combination of HCF₃ 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 in situ 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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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.