Details

Autor(en) / Beteiligte

• Yu, Xiao‐Ye
• Zhao, Quan‐Qing
• Chen, Jun
• Chen, Jia‐Rong
• Xiao, Wen‐Jing

Titel

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

Ist Teil von

• Angewandte Chemie International Edition, 2018-11, Vol.57 (47), p.15505-15509

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2018

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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.