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A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters
Author(s) -
Lima Fabio,
Sharma Upendra K.,
Grunenberg Lars,
Saha Debasmita,
Johannsen Sandra,
Sedelmeier Joerg,
Van der Eycken Erik V.,
Ley Steven V.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201709690
Subject(s) - chemistry , catalysis , alkyl , boronic acid , lewis acids and bases , aryl , photoredox catalysis , organic chemistry , base (topology) , redox , combinatorial chemistry , radical , mathematical analysis , mathematics , photocatalysis
We 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.