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Stereoselective C–O Silylation and Stannylation by Ying Hu; Jiali Peng; Binjing Hu; Jixin Wang; Jing Jing; Jie Lin; Xingchen Liu; Xiaotian Qi; Jie Li is a scholarly article available to read on EtoBox.

What is Stereoselective C–O Silylation and Stannylation about?

Abstract On the basis of umpolung strategy, a practical preparation of stereoselective tri- and tetrasubstituted alkenyl silanes and stannanes by performing cobalt-catalyzed cross-coupling between readily available alkenyl acetates and solid Me2PhSi‒ZnOPiv•Li2(Cl)(OPiv), as well as (nBu)3Sn‒ZnCl•LiCl under remarkably mild reaction conditions has been developed. In this reaction, direct C‒O bond silylation and stannylation character by their complete control of chemoselectivity, stereoselectivity, as well as excellent functional group compatibility, thus providing an expedient route to prepare tri- and tetrasubstituted alkenyl silanes and stannanes. The resulting polysubstituted alkenyl silanes and stannanes show high reactivity in arylation and alkenylation by Hiyama and Stille reactions. The synthetic utility of our protocol was further illustrated by the facile late-stage modifications of natural products and druglike molecules. Detailed mechanistic studies suggest that the reaction involves a chelation-assisted oxidative insertion of cobalt species to C‒O bond. We anticipate that our findings should prove instrumental for potential applications of this technology to organic synt

Author

Ying Hu; Jiali Peng; Binjing Hu; Jixin Wang; Jing Jing; Jie Lin; Xingchen Liu; Xiaotian Qi; Jie Li

Published

2022

Language

EN