3 years ago

Direct C–H Cyanoalkylation of Heteroaromatic N-Oxides and Quinones via C–C Bond Cleavage of Cyclobutanone Oximes

Direct C–H Cyanoalkylation of Heteroaromatic N-Oxides and Quinones via C–C Bond Cleavage of Cyclobutanone Oximes
Xin-Hua Duan, Lin Yang, Li-Na Guo, Yu-Rui Gu
A direct C–H cyanoalkylation of heteroaromatic N-oxides and quinones with cyclobutanone oximes is reported. This redox-neutral, operationally simple cyanoalkylation reaction is successfully amenable to a wide range of heteroaromatic N-oxides, quinones, and cyclobutanone oximes. A novel catalytic system consisting of a nickel source proved crucial for cleavage of the C–C bond of cyclobutanone oximes and for selective C–C bond formation over β-hydride elimination. Mechanistic studies suggest that a radical intermediate might be involved in this transformation.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02902

DOI: 10.1021/acs.orglett.7b02902

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