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Copper‐Catalyzed Intermolecular Heck‐Like Coupling of Cyclobutanone Oximes Initiated by Selective C−C Bond Cleavage
Author(s) -
Zhao Binlin,
Shi Zhuangzhi
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201707181
Subject(s) - chemistry , cyclobutanone , catalysis , bond cleavage , olefin fiber , intermolecular force , photochemistry , heck reaction , combinatorial chemistry , copper , medicinal chemistry , organic chemistry , palladium , molecule , ring (chemistry)
Abstract The first example of intermolecular olefination of cyclobutanone oximes with alkenes via selective C−C bond cleavage leading to the synthesis of nitriles in the presence of a cheap copper catalyst is reported. The procedure is distinguished by mild and safe reaction conditions that avoid ligand, oxidant, base, or toxic cyanide salt. A wide scope of cyclobutanones and olefin coupling components can be used without compromising efficiency and scalability. The alternative visible‐light‐driven photoredox process for this coupling reaction was also uncovered.