3 years ago

Copper-Catalyzed Intermolecular Heck-Like Coupling of Cyclobutanone Oximes Initiated by Selective C−C Bond Cleavage

Copper-Catalyzed Intermolecular Heck-Like Coupling of Cyclobutanone Oximes Initiated by Selective C−C Bond Cleavage
Zhuangzhi Shi, Binlin Zhao
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. No construction without destruction: A copper-catalyzed intermolecular olefination of cyclobutanone oximes with alkenes by C−C activation has been established. The method features mild and safe reaction conditions that avoid ligand, oxidant, base, or toxic cyanide salt, and a wide scope of cyclobutanones and olefin coupling components can be used without compromising efficiency and scalability.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201707181

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