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Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines.

ABSTRACT: We report herein studies on copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines. Treatment of N-H ketimines having an ?-sp(3) hybridized carbon under Cu-catalyzed aerobic reaction conditions resulted in a radical fragmentation with C-C bond cleavage to give the corresponding carbonitrile and carbon radical intermediate. This radical process has been applied for the construction of oxaspirocyclohexadienones as well as in the electrophilic cyanation of Grignard reagents with pivalonitrile as a CN source.

SUBMITTER: Tnay YL

PROVIDER: S-EPMC4661020 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines.

Tnay Ya Lin YL Ang Gim Yean GY Chiba Shunsuke S

Beilstein journal of organic chemistry 20151019

We report herein studies on copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines. Treatment of N-H ketimines having an α-sp(3) hybridized carbon under Cu-catalyzed aerobic reaction conditions resulted in a radical fragmentation with C-C bond cleavage to give the corresponding carbonitrile and carbon radical intermediate. This radical process has been applied for the construction of oxaspirocyclohexadienones as well as in the electrophilic cyanation of Grignard reagents with pivalo ...[more]

PMID: 26664613

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