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

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 sys...

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Published inOrganic letters Vol. 19; no. 21; pp. 5908 - 5911
Main Authors Gu, Yu-Rui, Duan, Xin-Hua, Yang, Lin, Guo, Li-Na
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.11.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
KETONES
HETEROCYCLES
O-BENZOYLOXIMES
AMINES
TERTIARY CYCLOALKANOLS
TIN
IMINYL RADICALS
ALKYL NITRILES
ALDEHYDES
RING-CLEAVAGE
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b02902