Iron-Catalyzed ortho C−H Arylation and Methylation of Pivalophenone N−H Imines

Wengang Xu, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

Abstract

Iron-catalyzed ortho C−H arylation and methylation reactions of pivalophenone N−H imines are reported. The pivaloyl N−H imine proved an excellent directing group for the arylation with diarylzinc reagents in the presence of an iron-diphosphine catalyst and 2,3-dichlorobutane at room temperature. A similar catalytic system also allowed methylation with Me3Al at 70 °C. The pivaloyl imine of the product could be readily converted to a cyano group, thus allowing convenient preparation of ortho-functionalized benzonitriles.

Original languageEnglish
Pages (from-to)3049-3053
Number of pages5
JournalChemSusChem
Volume12
Issue number13
DOIs
Publication statusPublished - 2019 Jul 5
Externally publishedYes

Keywords

  • arylation
  • C−H activation
  • iron
  • methylation
  • organometallic reagents

ASJC Scopus subject areas

  • Environmental Chemistry
  • Chemical Engineering(all)
  • Materials Science(all)
  • Energy(all)

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