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

doi:10.1021/acscatal.6b00149

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

Rutgers University

Research output: Contribution to journal › Article › peer-review

12 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 language	English
Pages (from-to)	2836-2841
Number of pages	6
Journal	ACS Catalysis
Volume	6
Issue number	5
DOIs	https://doi.org/10.1021/acscatal.6b00149
Publication status	Published - 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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title = "Alkyl-Aryl Coupling Catalyzed by Tandem Systems of Pincer-Ligated Iridium Complexes and Zeolites",

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.",

keywords = "C-C coupling, C-H activation, alkane dehydrogenation, dehydrogenative cross-coupling, pincer ligand, tandem catalysis, zeolite",

author = "Dinh, {Long V.} and Bo Li and Akshai Kumar and William Schinski and Field, {Kathleen D.} and Alexander Kuperman and Celik, {Fuat E.} and Goldman, {Alan S.}",

note = "Funding Information: This work was supported by NSF under the CCI Center for Enabling New Technologies through Catalysis (CENTC) Phase II Renewal, CHE-1205189, and by Chevron Energy Technology Company. Publisher Copyright: {\textcopyright} 2016 American Chemical Society. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.",

year = "2016",

month = may,

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doi = "10.1021/acscatal.6b00149",

language = "English",

volume = "6",

pages = "2836--2841",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Alkyl-Aryl Coupling Catalyzed by Tandem Systems of Pincer-Ligated Iridium Complexes and Zeolites

AU - Dinh, Long V.

AU - Li, Bo

AU - Kumar, Akshai

AU - Schinski, William

AU - Field, Kathleen D.

AU - Kuperman, Alexander

AU - Celik, Fuat E.

AU - Goldman, Alan S.

N1 - Funding Information: This work was supported by NSF under the CCI Center for Enabling New Technologies through Catalysis (CENTC) Phase II Renewal, CHE-1205189, and by Chevron Energy Technology Company. Publisher Copyright: © 2016 American Chemical Society. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.

PY - 2016/5/6

Y1 - 2016/5/6

N2 - 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.

AB - 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.

KW - C-C coupling

KW - C-H activation

KW - alkane dehydrogenation

KW - dehydrogenative cross-coupling

KW - pincer ligand

KW - tandem catalysis

KW - zeolite

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

Abstract

Keywords

ASJC Scopus subject areas

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