Protocol for synthesizing both racemic and chiral allenylsilanes through copper-catalyzed silylation of propargyl dichlorides

Chiral allenylsilanes serve as crucial intermediates in the synthesis of complex pharmaceutical molecules and natural products. Here, we present a protocol for synthesizing both racemic and chiral allenylsilanes through copper-catalyzed silylation of propargyl dichlorides. We describe steps for the SN<sub>2</sub>' propargyl silylation reaction between propargyl dichlorides and a silylboronate, followed by the purification of the products. The obtained optically active chloro-substituted allenylsilane products can be readily transformed into various useful allene derivatives, demonstrating the high synthetic value of this methodology. For complete details on the use and execution of this protocol, please refer to Liu et al.<sup>1</sup>.

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Publication Details

Journal
STAR Protocols
Published
2025-08-08
DOI
https://doi.org/10.1016/j.xpro.2025.104022
Primary Topic
Catalytic Alkyne Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Protocol for synthesizing both racemic and chiral allenylsilanes through copper-catalyzed silylation of propargyl dichlorides

Ying Zhou, Zhengli Liu
1 links
STAR Protocols
Catalytic Alkyne Reactions
article

Protocol for synthesizing both racemic and chiral allenylsilanes through copper-catalyzed silylation of propargyl dichlorides

Ying Zhou, Zhengli Liu
article en

Abstract

Chiral allenylsilanes serve as crucial intermediates in the synthesis of complex pharmaceutical molecules and natural products. Here, we present a protocol for synthesizing both racemic and chiral allenylsilanes through copper-catalyzed silylation of propargyl dichlorides. We describe steps for the SN<sub>2</sub>' propargyl silylation reaction between propargyl dichlorides and a silylboronate, followed by the purification of the products. The obtained optically active chloro-substituted allenylsilane products can be readily transformed into various useful allene derivatives, demonstrating the high synthetic value of this methodology. For complete details on the use and execution of this protocol, please refer to Liu et al.<sup>1</sup>.

STAR ProtocolsVol. 6(3)
Nanchang University (CN)
National Natural Science Foundation of China
Clean water and sanitation
Openalex Percentile: Top 85%
Catalytic Alkyne Reactions
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