Cobalt-Promoted Electroreductive Cross-Coupling of Prop-2-yn-1-yl Acetates with Chloro(vinyl)silanes

An electroreductive cross-coupling of prop-2-yn-1-yl acetates with chloro­(vinyl)­silanes for producing tetrasubstituted silylallenes is developed. The method enables the formation of a new CSi bond through the cathodic reduction formation of the silyl radical, radical addition across the CC bond,...

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Bibliographic Details
Published in:Organic letters 2023-10, Vol.25 (39), p.7263-7267
Main Authors: Xu, Chong-Hui, Xiong, Zhi-Qiang, Qin, Jing-Hao, Xu, Xin-Hua, Li, Jin-Heng
Format: Article
Language:English
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Summary:An electroreductive cross-coupling of prop-2-yn-1-yl acetates with chloro­(vinyl)­silanes for producing tetrasubstituted silylallenes is developed. The method enables the formation of a new CSi bond through the cathodic reduction formation of the silyl radical, radical addition across the CC bond, the alkenyl anion intermediate formation, and deacetoxylation and represents a mild, practical route to the synthesis of silylallenes. Mechanistic studies reveal that CoCl2 acts as the mediator to promote the formation of the alkenyl anion intermediate via electron transfer.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c02989