Palladium-catalyzed oxidative ethoxycarbonylation of aromatic C-H bond with diethyl azodicarboxylate

Wing Yiu Yu, Nga Sit Wing, Kin Man Lai, Zhongyuan Zhou, Albert S.C. Chan

Research output: Journal article publicationJournal articleAcademic researchpeer-review

178 Citations (Scopus)

Abstract

This communication describes the Pd(OAc)2-catalyzed ethoxycarbonylation reactions of aromatic C-H bonds using diethyl azodicarboxylate (DEAD) together with Oxone or K2S2O8. Substrates such as 2-arylpyridines, pyrrolidinone, acetylindoline, quinoline, and oximes were ethoxycarbonylated with excellent chemo- and regioselectivities. The catalytic reaction is probably initiated by chelation-assisted cyclopalladation of the ortho-C-H bond. Preliminary studies suggested that reactive ethoxyacyl radicals generated from thermal decomposition of DEAD were involved in the ester formation.
Original languageEnglish
Pages (from-to)3304-3306
Number of pages3
JournalJournal of the American Chemical Society
Volume130
Issue number11
DOIs
Publication statusPublished - 19 Mar 2008

ASJC Scopus subject areas

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

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