Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 47, Pages 15136-15140Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201709690
Keywords
boronic acids; cross-coupling; Lewis base catalysis; photoredox catalysis; synthetic methods
Categories
Funding
- Novartis Pharma AG
- Erasmus Scholarship Scheme
- EPSRC [EP/K009494/1, EP/K039520/1, EP/M004120/1]
- University of Leuven
- FWO
- Ministry of Education and Science of the Russian Federation [02.a03.0008]
- EPSRC [EP/M004120/1, EP/K039520/1, EP/K009494/1] Funding Source: UKRI
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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.
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