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Electrochemically Driven Deoxygenative Borylation of Alcohols and Carbonyl Compounds

Weiyang Guan, Yejin Chang, Song Lin

2023Journal of the American Chemical Society67 citationsDOIOpen Access PDF

Abstract

We present a new, unified approach for the transformation of benzylic and allylic alcohols, aldehydes, and ketones into boronic esters under electroreductive conditions. Key to our strategy is the use of readily available pinacolborane, which serves both as an activator and an electrophile by first generating a redox-active trialkylborate species and then delivering the desired deoxygenatively borylated product. This strategy is applicable to a variety of substrates and can be employed for the late-stage functionalization of complex molecules.

Topics & Concepts

ChemistryBorylationAllylic rearrangementElectrophileCombinatorial chemistryOrganic chemistrySurface modificationCatalysisArylAlkylPhysical chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOrganoboron and organosilicon chemistry
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