Copper‐Catalyzed Borylacylation of Activated Alkenes with Acid Chlorides

A method for the copper‐catalyzed borylacylation of activated alkenes is presented. The reaction involves borylcupration of the alkene, followed by capture of the generated alkyl–copper intermediate with an acid chloride. The reactions operated with low catalyst loading and generally occurre within...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-10, Vol.56 (43), p.13314-13318
Main Authors: Huang, Yuan, Smith, Kevin B., Brown, M. Kevin
Format: Article
Language:English
Subjects:
acid chlorides
Acids
Acylation
Alkenes
Alkenes - chemistry
Aromatic compounds
Benzoates - chemistry
boron
Boron Compounds - chemistry
Catalysis
Chlorides
Chlorides - chemistry
Copper
Copper - chemistry
Crystallography, X-Ray
Enantiomers
homogeneous catalysis
Molecular Conformation
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Summary:A method for the copper‐catalyzed borylacylation of activated alkenes is presented. The reaction involves borylcupration of the alkene, followed by capture of the generated alkyl–copper intermediate with an acid chloride. The reactions operated with low catalyst loading and generally occurre within 15 min at room temperature for a range of activated alkenes. In the case of vinyl arenes, enantioselective borylacylation was possible. Give 'em the new one, two: A range of activated alkenes underwent rapid copper‐catalyzed borylacylation at room temperature at low catalyst loadings (see scheme). The reaction involves borylcupration of the alkene and capture of the resulting alkyl–copper intermediate with an acid chloride. In the case of vinyl arenes, the transformation could be carried out in an enantioselective manner.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201707323