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

Binlin Zhao; Zhuangzhi Shi

doi:10.1002/anie.201707181

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

Angew Chem Int Ed Engl. 2017 Oct 2;56(41):12727-12731. doi: 10.1002/anie.201707181. Epub 2017 Sep 1.

Authors

Binlin Zhao¹, Zhuangzhi Shi¹

Affiliation

¹ State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.

PMID: 28861945
DOI: 10.1002/anie.201707181

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.

Keywords: copper; cyclobutanone; olefination; oximes; radicals.

Publication types

Research Support, Non-U.S. Gov't