Copper‐Catalyzed Radical Cross‐Coupling of Redox‐Active Oxime Esters, Styrenes, and Boronic Acids

A visible‐light‐driven, copper‐catalyzed three‐component radical cross‐coupling of oxime esters, styrenes, and boronic acids has been developed. Key steps of this protocol involve catalytic generation of an iminyl radical from a redox‐active oxime ester and subsequent C−C bond cleavage to generate a...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-11, Vol.57 (47), p.15505-15509
Main Authors: Yu, Xiao‐Ye, Zhao, Quan‐Qing, Chen, Jun, Chen, Jia‐Rong, Xiao, Wen‐Jing
Format: Article
Language:English
Subjects:
Acids
Catalysis
Copper
Coupling
cross-coupling
Esters
Oxime esters
photochemistry
radicals
Styrene
Styrenes
synthetic methods
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Summary:A visible‐light‐driven, copper‐catalyzed three‐component radical cross‐coupling of oxime esters, styrenes, and boronic acids has been developed. Key steps of this protocol involve catalytic generation of an iminyl radical from a redox‐active oxime ester and subsequent C−C bond cleavage to generate a cyanoalkyl radical. Upon its addition to styrene, the newly formed benzylic radical undergoes coupling with a boronic‐acid‐derived ArCuII complex to achieve 1,1‐diarylmethane‐containing alkylnitriles. Key steps of the visible‐light‐driven title reaction involve catalytic generation of an iminyl radical from a redox‐active oxime ester and subsequent C−C bond cleavage to give a cyanoalkyl radical. Upon its addition to styrene, a benzylic radical is formed that undergoes coupling with a boronic‐acid‐derived ArCuII complex to give 1,1‐diarylmethane‐containing alkylnitriles. The method features the use of readily available substrates and high functional‐group tolerance.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201809820