Alkyl-Aryl Coupling Catalyzed by Tandem Systems of Pincer-Ligated Iridium Complexes and Zeolites

Long V. Dinh, Bo Li, Akshai Kumar, William Schinski, Kathleen D. Field, Alexander Kuperman, Fuat E. Celik, Alan S. Goldman

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

We report that pincer-ligated iridium catalysts for alkane dehydrogenation can operate in tandem with zeolite catalysts for arene-alkene coupling, to effect the overall intramolecular dehydrocoupling of alkyl-H and aryl-H bonds (i.e., the dehydrocyclization of alkyl benzene). Thus, zeolite and soluble iridium cocatalysts in refluxing pentylbenzene (205 °C) gave high yields of 1-methyl-1,2,3,4-tetrahydronaphthalene. Subsequent dehydrogenation and isomerization affords 1- and 2-methylnaphthalene and 2-methyl-1,2,3,4-tetrahydronaphthalene. Total yields of cyclized product as high as 5.4 M (94%) have been obtained, corresponding to 6800 turnovers per mol Ir. Turnover numbers for the tandem-catalyzed dehydrocyclization are much greater than those obtained for simple dehydrogenation by Ir catalysts (to give olefins) in the absence of zeolite.

Original languageEnglish
Pages (from-to)2836-2841
Number of pages6
JournalACS Catalysis
Volume6
Issue number5
DOIs
Publication statusPublished - May 6 2016

Keywords

  • C-C coupling
  • C-H activation
  • alkane dehydrogenation
  • dehydrogenative cross-coupling
  • pincer ligand
  • tandem catalysis
  • zeolite

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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  • Cite this

    Dinh, L. V., Li, B., Kumar, A., Schinski, W., Field, K. D., Kuperman, A., Celik, F. E., & Goldman, A. S. (2016). Alkyl-Aryl Coupling Catalyzed by Tandem Systems of Pincer-Ligated Iridium Complexes and Zeolites. ACS Catalysis, 6(5), 2836-2841. https://doi.org/10.1021/acscatal.6b00149