Intermolecular amidation of unactivated sp2 and sp3 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion

Hung Yat Thu, Wing Yiu Yu, Chi Ming Che

Research output: Journal article publicationJournal articleAcademic researchpeer-review

593 Citations (Scopus)

Abstract

This communication describes the Pd(OAc)2-catalyzed intermolecular amidation reactions of unactivated sp2 and sp3 C-H bonds using primary amides and potassium persulfate. The substrates containing a pendent oxime or pyridine group were amidated with excellent chemo- and regioselectivities. It is noteworthy that reactive C-X bonds were well-tolerated and a variety of primary amides can be effective nucleophiles for the Pd-catalyzed C-H amidation reactions. For the reaction of unactivated sp3 C-H bonds, β-amidation of 1° sp3 C-H bonds versus 2° C-H bonds is preferred. The catalytic reaction is initiated by chelation-assisted cyclopalladation involving C-H bond activation. Preliminary mechanistic study suggested that the persulfate oxidation of primary amides should generate reactive nitrene species, which then reacted with the cyclopalladated complex.
Original languageEnglish
Pages (from-to)9048-9049
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number28
DOIs
Publication statusPublished - 19 Jul 2006

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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