Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 8, Pages 2155-2159Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201712186
Keywords
amino acids; boron; photochemistry; radical reactions; reaction mechanisms
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Funding
- EPSRC [EP/I038071/1]
- H2020 ERC [670668]
- Deutsche Forschungsgemeinschaft (DFG) fellowship
- EPSRC [EP/L011999/1, EP/K03927X/1, EP/I038071/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K03927X/1, EP/I038071/1, EP/L011999/1] Funding Source: researchfish
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The synthesis of alkyl boronic esters by direct decarboxylative radical addition of carboxylic acids to vinyl boronic esters is described. The reaction proceeds under mild photoredox catalysis and involves an unprecedented single-electron reduction of an alpha-boryl radical intermediate to the corresponding anion. The reaction is amenable to a diverse range of substrates, including alpha-amino, alpha-oxy, and alkyl carboxylic acids, thus providing a novel method to rapidly access boron-containing molecules of potential biological importance.
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