Zn-Mediated Cross Coupling of Alkynyl Bromides and Polychlorosilanes

A Zn-mediated, transition-metal- and ligand-free synthesis of alkynylsilanes from alkynyl bromides and polychlorosilanes is reported. A wide range of alkynyl bromides and chlorosilanes, including monochlorosilanes, afford alkynylsilanes in moderate to excellent yields. The products allow for diverse downstream functionalization. Control experiments and DFT calculations support an S<sub>N</sub>2-type substitution pathway involving an alkynylzinc intermediate and chlorosilanes. This protocol offers a practical and general approach to access diverse alkynylsilanes from readily accessible precursors.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-12-23
DOI
https://doi.org/10.1021/acs.joc.5c02374
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
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article

Zn-Mediated Cross Coupling of Alkynyl Bromides and Polychlorosilanes

Yan-Lin Zhang, Xiaoting Zou, Liangquan Sheng, Xi Chen et al.
The Journal of Organic Chemistry
Catalytic Cross-Coupling Reactions
article

Zn-Mediated Cross Coupling of Alkynyl Bromides and Polychlorosilanes

Yan-Lin Zhang, Xiaoting Zou, Liangquan Sheng, Xi Chen, Pan Pan, Huajie Xu, Wenwen Huang, Jingcao Li
article en

Abstract

A Zn-mediated, transition-metal- and ligand-free synthesis of alkynylsilanes from alkynyl bromides and polychlorosilanes is reported. A wide range of alkynyl bromides and chlorosilanes, including monochlorosilanes, afford alkynylsilanes in moderate to excellent yields. The products allow for diverse downstream functionalization. Control experiments and DFT calculations support an S<sub>N</sub>2-type substitution pathway involving an alkynylzinc intermediate and chlorosilanes. This protocol offers a practical and general approach to access diverse alkynylsilanes from readily accessible precursors.

The Journal of Organic ChemistryVol. 91(1)
Fuyang Normal University (CN), Southern University of Science and Technology (CN), Biomass Technology Group (Netherlands) (NL), Jiangmen Polytechnic (CN), State Key Laboratory of Applied Organic Chemistry, Lanzhou University (CN), Green Cross International (US)
Openalex Percentile: Top 34%
Catalytic Cross-Coupling Reactions
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