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Pivalophenone imine as a benzonitrile surrogate for directed C–H bond functionalization

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Abstract

Pivalophenone N–H imine has been found to serve as a prominent substrate for directed C–H alkylation and arylation reactions with alkyl bromides and aryl chlorides, respectively, under cobalt–N-heterocyclic carbene (NHC) catalysis. Unlike the case of the parent pivalophenone imine, the increased steric bulk of the resulting ortho-substituted pivalophenone imines allows them to undergo clean imine-to-nitrile conversion under peroxide photolysis or aerobic copper catalysis conditions. Overall, these two-step transformations offer convenient synthetic methods for ortho-functionalized benzonitriles.

Graphical abstract: Pivalophenone imine as a benzonitrile surrogate for directed C–H bond functionalization

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Publication details

The article was received on 19 Apr 2017, accepted on 29 May 2017 and first published on 30 May 2017


Article type: Edge Article
DOI: 10.1039/C7SC01732D
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY-NC license
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    Pivalophenone imine as a benzonitrile surrogate for directed C–H bond functionalization

    W. Xu and N. Yoshikai, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC01732D

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