Difluorocarbene-Mediated Trimethylsilylation of Nucleophiles with 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.
Authors
- Shifa Zhu (ORCID: https://orcid.org/0000-0001-5172-7152)
- Dong Zhu (ORCID: https://orcid.org/0000-0002-7365-5556)
- Hao Ruan
- Jingwei Zhao
Institutions
- Zhejiang Sci-Tech University (CN)
- Jiujiang University (CN)
- Key Laboratory of Guangdong Province (CN)
- South China University of Technology (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-02-10
- DOI
- https://doi.org/10.1021/acs.orglett.5c00227
- Citations
- 3
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 2.37
Funders
- National Natural Science Foundation of China
- Basic and Applied Basic Research Foundation of Guangdong Province