Abstract
AbstractWe report herein the use of a dual catalytic system comprising a Lewis base catalyst such as quinuclidin‐3‐ol or 4‐dimethylaminopyridine and a photoredox catalyst to generate carbon radicals from either boronic acids or esters. This system enabled a wide range of alkyl boronic esters and aryl or alkyl boronic acids to react with electron‐deficient olefins via radical addition to efficiently form C−C coupled products in a redox‐neutral fashion. The Lewis base catalyst was shown to form a redox‐active complex with either the boronic esters or the trimeric form of the boronic acids (boroxines) in solution.
Highlights
We report the use of a dual catalytic system comprising a Lewis base catalyst such as quinuclidin-3-ol or 4-dimethylaminopyridine and a photoredox catalyst to generate carbon radicals from either boronic acids or esters
By enabling visible-light-promoted single electron transfer, photoredox catalysis has become a method of choice for the single-electron reduction or oxidation of organic substrates and allows to generate open-shell intermediates in a mild and selective fashion.[4]
Oxidative carbon radical precursors are often anionic species suffering from poor solubility in common organic solvents
Summary
We report the use of a dual catalytic system comprising a Lewis base catalyst such as quinuclidin-3-ol or 4-dimethylaminopyridine and a photoredox catalyst to generate carbon radicals from either boronic acids or esters. We describe a dual catalytic method to effectively form alkyl and aryl radicals from a wide array of boronic esters and acids by direct photoredox single-electron oxidation under mild and safe conditions, without the requirement for stoichiometric activators or oxidants.
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