Mechanism of benzoquinone-promoted palladium-catalyzed oxidative cross-coupling reactions

Kami Lee Hull, Melanie S. Sanford

Research output: Contribution to journalArticlepeer-review

Abstract

(Chemical Equation Presented) This communication describes mechanistic studies of the Pd-catalyzed oxidative cross-coupling of benzo[h]quinoline with simple arenes. Through a series of experiments, including determination of the order of the reaction in various reagents, H/D exchange studies, kinetic isotope effect investigations, and the evaluation of electronic effects, we propose a detailed mechanism for these reactions. Importantly, this mechanism explains the key role of benzoquinone in these transformations; in addition, it provides insights that allow the rational tuning of reaction conditions to control the chemoselectivity of Ar-Ar′ coupling.

Original languageEnglish (US)
Pages (from-to)9651-9653
Number of pages3
JournalJournal of the American Chemical Society
Volume131
Issue number28
DOIs
StatePublished - Jul 22 2009

ASJC Scopus subject areas

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

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