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

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Cobalt-Promoted Electroreductive Cross-Coupling of Prop-2-yn-1-yl Acetates with Chloro(vinyl)silanes
Organic Letters ( IF 4.9 ) Pub Date : 2023-09-27 , DOI: 10.1021/acs.orglett.3c02989
Chong-Hui Xu _{1,

2} , Zhi-Qiang Xiong ₂ , Jing-Hao Qin ₂ , Xin-Hua Xu ₁ , Jin-Heng Li _{1,

2,

3,

4}

Affiliation

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.

中文翻译：

钴促进的乙酸丙-2-yn-1-基酯与氯（乙烯基）硅烷的电还原交叉偶联

开发了乙酸丙-2-炔-1-基酯与氯（乙烯基）硅烷的电还原交叉偶联，用于生产四取代的硅基丙二烯。该方法通过甲硅烷基自由基的阴极还原形成、C−C 键上的自由基加成、烯基阴离子中间体的形成以及脱乙酰氧基化，能够形成新的 C─Si 键，并且代表了一种温和、实用的合成路线甲硅烷基丙二烯。机理研究表明CoCl ₂作为介体通过电子转移促进烯基阴离子中间体的形成。

更新日期：2023-09-27

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