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

Wengang Xu, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5299-5304
Number of pages6
JournalChemical Science
Volume8
Issue number8
DOIs
Publication statusPublished - 2017
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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