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 | |
| Publication status | Published - May 6 2016 |
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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 journal › Article
}
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
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 - alkane dehydrogenation
KW - C-C coupling
KW - C-H activation
KW - dehydrogenative cross-coupling
KW - pincer ligand
KW - tandem catalysis
KW - zeolite
UR - http://www.scopus.com/inward/record.url?scp=84973539291&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84973539291&partnerID=8YFLogxK
U2 - 10.1021/acscatal.6b00149
DO - 10.1021/acscatal.6b00149
M3 - Article
AN - SCOPUS:84973539291
VL - 6
SP - 2836
EP - 2841
JO - ACS Catalysis
JF - ACS Catalysis
SN - 2155-5435
IS - 5
ER -