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

8 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

Fingerprint

Zeolites
Iridium
Dehydrogenation
Alkenes
Catalysts
Olefins
Alkanes
Isomerization
Benzene
Paraffins
tetralin

Keywords

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

ASJC Scopus subject areas

  • Catalysis

Cite this

Alkyl-Aryl Coupling Catalyzed by Tandem Systems of Pincer-Ligated Iridium Complexes and Zeolites. / Dinh, Long V.; Li, Bo; Kumar, Akshai; Schinski, William; Field, Kathleen D.; Kuperman, Alexander; Celik, Fuat E.; Goldman, Alan S.

In: ACS Catalysis, Vol. 6, No. 5, 06.05.2016, p. 2836-2841.

Research output: Contribution to journalArticle

Dinh, LV, Li, B, Kumar, A, Schinski, W, Field, KD, Kuperman, A, Celik, FE & Goldman, AS 2016, 'Alkyl-Aryl Coupling Catalyzed by Tandem Systems of Pincer-Ligated Iridium Complexes and Zeolites', ACS Catalysis, vol. 6, no. 5, pp. 2836-2841. https://doi.org/10.1021/acscatal.6b00149
Dinh, Long V. ; Li, Bo ; Kumar, Akshai ; Schinski, William ; Field, Kathleen D. ; Kuperman, Alexander ; Celik, Fuat E. ; Goldman, Alan S. / Alkyl-Aryl Coupling Catalyzed by Tandem Systems of Pincer-Ligated Iridium Complexes and Zeolites. In: ACS Catalysis. 2016 ; Vol. 6, No. 5. pp. 2836-2841.
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