Cobalt-Promoted Electroreductive Cross-Coupling of Prop-2-yn-1-yl Acetates with Chloro(vinyl)silanes
Chong‐Hui Xu, Zhiqiang Xiong, Jing‐Hao Qin, Xinhua Xu, Jin‐Heng Li
Abstract
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 CoCl 2 acts as the mediator to promote the formation of the alkenyl anion intermediate via electron transfer.
Topics & Concepts
SilanesChemistrySilylationCathodic protectionMedicinal chemistryPhotochemistryPolymer chemistryCatalysisOrganic chemistryElectrochemistrySilaneElectrodePhysical chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques