A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters. Issue 47 (24th October 2017)

• Record Type: Journal Article
• Authors: Lima, Fabio; Sharma, Upendra K.; Grunenberg, Lars; Saha, Debasmita; Johannsen, Sandra; Sedelmeier, Joerg; Van der Eycken, Erik V.; Ley, Steven V.
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 47(2017)
• Page Start: 15136
• Page End: 15140
• Publication Date: 2017-10-24
• Subjects: boronic acids -- cross-coupling -- Lewis base catalysis -- photoredox catalysis -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201709690
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : Boronic acids turn photoactivable : A dual catalytic system comprising a Lewis base catalyst (LB) such as quinuclidin‐3‐ol or 4‐dimethylaminopyridine and a photoredox catalyst enables the generation of carbon radicals from either boronic acids or esters. A wide range of alkyl boronic esters and aryl or alkyl boronic acids reacted with electron‐deficient olefins to form C−C coupled products in a redox‐neutral fashion.