Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 11, Pages 4375-4379Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201916340
Keywords
alkyl boronic esters; carboxylic acids; conjunctive cross-coupling; decarboxylative cross-coupling; metallaphotoredox catalysis
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Funding
- H2020 ERC [670668]
- National University of Ireland
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The synthesis of complex alkyl boronic esters through conjunctive cross-coupling of vinyl boronic esters with carboxylic acids and aryl iodides is described. The reaction proceeds under mild metallaphotoredox conditions and involves an unprecedented decarboxylative radical addition/cross-coupling cascade of vinyl boronic esters. Excellent functional-group tolerance is displayed, and application of a range of carboxylic acids, including secondary alpha-amino acids, and aryl iodides provides efficient access to highly functionalized alkyl boronic esters. The decarboxylative conjunctive cross-coupling was also applied to the synthesis of sedum alkaloids.
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