Improved turnover numbers in palladium-catalyzed bisdiene cyclization-trapping using N-heterocyclic carbene ligands

James M. Takacs, Suman Layek, Hector Palencia, Ross N. Andrews

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

An optimized palladium-N-heterocyclic carbene catalyst system effects the palladium-catalyzed bisdiene cyclization-trapping with phenol at the 0.01% catalyst loading level with a TON of 7.6 × 103 and TOF of 280 h-1, values much higher than typically found for this and related carbocyclizations. The reaction scales well and the trans-substituted six-membered ring product is obtained in excellent yield on a 10-mmole scale without further optimization of the catalyst system or reaction conditions.

Original languageEnglish (US)
Pages (from-to)1937-1942
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume347
Issue number15
DOIs
Publication statusPublished - Dec 1 2005

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Keywords

  • C-C coupling
  • Cyclization
  • Homogeneous catalysis
  • N-heterocyclic carbenes
  • Palladium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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