Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
4 years ago

A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters

Fabio Lima, Erik V Van der Eycken, Upendra K Sharma, Lars Grunenberg, Joerg Sedelmeier, Sandra Johannsen, Steven Victor Ley, Debasmita Saha
We report herein the use of a dual catalytic system comprising of a Lewis base catalyst such as quinuclidin-3-ol or 4-dimethylaminopyridine combined with 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 via radical addition with electron-deficient olefins 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 boronic esters or the trimeric form of the boronic acids (boroxines) in solution.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201709690

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