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Silyl Radical Generation from Silylboronic Pinacol Esters through Substitution with Aminyl Radicals

Hongyan Lan, Xiangyu Huo, Ying‐Gang Jia, Dingyi Wang

2024Organic Letters27 citationsDOI

Abstract

A novel strategy was developed to generate silyl radicals from silylboronic pinacol esters (SPEs) through nucleohomolytic substitution of boron with aminyl radicals. We successfully applied this strategy to obtain diverse organosilicon compounds using SPEs and N -nitrosamines under photoirradiation without any catalyst. The ability to access silyl radicals offers a new perspective for chemists to rapidly construct Si–X bonds.

Topics & Concepts

RadicalChemistrySilylationPinacolOrganosiliconBoronPhotochemistrySubstitution (logic)CatalysisOrganic chemistryMedicinal chemistryProgramming languageComputer scienceRadical Photochemical ReactionsOrganoboron and organosilicon chemistrySulfur-Based Synthesis Techniques
Silyl Radical Generation from Silylboronic Pinacol Esters through Substitution with Aminyl Radicals | Litcius