Catalytic dehydroaromatization of n-alkanes by pincer-ligated iridium complexes

Ritu Ahuja, Benudhar Punji, Michael Findlater, Carolyn Supplee, William Schinski, Maurice Brookhart, Alan S Goldman

Research output: Contribution to journalArticle

122 Citations (Scopus)

Abstract

Aromatic hydrocarbons are among the most important building blocks in the chemical industry. Benzene, toluene and xylenes are obtained from the high temperature thermolysis of alkanes. Higher alkylaromatics are generally derived from arene-olefin coupling, which gives branched products-that is, secondary alkyl arenes-with olefins higher than ethylene. The dehydrogenation of acyclic alkanes to give alkylaromatics can be achieved using heterogeneous catalysts at high temperatures, but with low yields and low selectivity. We present here the first catalytic conversion of n-alkanes to alkylaromatics using homogeneous or molecular catalysts-specifically 'pincerg'-ligated iridium complexes-and olefinic hydrogen acceptors. For example, the reaction of n-octane affords up to 86% yield of aromatic product, primarily o-xylene and secondarily ethylbenzene. In the case of n-decane and n-dodecane, the resulting alkylarenes are exclusively unbranched (that is, n-alkyl-substituted), with selectivity for the corresponding o-(n-alkyl)toluene.

Original languageEnglish
Pages (from-to)167-171
Number of pages5
JournalNature Chemistry
Volume3
Issue number2
DOIs
Publication statusPublished - Feb 2011

Fingerprint

Iridium
Alkanes
Paraffins
Toluene
Alkenes
Xylene
Olefins
Aromatic Hydrocarbons
Xylenes
Thermolysis
Catalysts
Ethylbenzene
Aromatic hydrocarbons
Dehydrogenation
Chemical industry
Benzene
Hydrogen
Ethylene
Temperature

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Ahuja, R., Punji, B., Findlater, M., Supplee, C., Schinski, W., Brookhart, M., & Goldman, A. S. (2011). Catalytic dehydroaromatization of n-alkanes by pincer-ligated iridium complexes. Nature Chemistry, 3(2), 167-171. https://doi.org/10.1038/nchem.946

Catalytic dehydroaromatization of n-alkanes by pincer-ligated iridium complexes. / Ahuja, Ritu; Punji, Benudhar; Findlater, Michael; Supplee, Carolyn; Schinski, William; Brookhart, Maurice; Goldman, Alan S.

In: Nature Chemistry, Vol. 3, No. 2, 02.2011, p. 167-171.

Research output: Contribution to journalArticle

Ahuja, R, Punji, B, Findlater, M, Supplee, C, Schinski, W, Brookhart, M & Goldman, AS 2011, 'Catalytic dehydroaromatization of n-alkanes by pincer-ligated iridium complexes', Nature Chemistry, vol. 3, no. 2, pp. 167-171. https://doi.org/10.1038/nchem.946
Ahuja R, Punji B, Findlater M, Supplee C, Schinski W, Brookhart M et al. Catalytic dehydroaromatization of n-alkanes by pincer-ligated iridium complexes. Nature Chemistry. 2011 Feb;3(2):167-171. https://doi.org/10.1038/nchem.946
Ahuja, Ritu ; Punji, Benudhar ; Findlater, Michael ; Supplee, Carolyn ; Schinski, William ; Brookhart, Maurice ; Goldman, Alan S. / Catalytic dehydroaromatization of n-alkanes by pincer-ligated iridium complexes. In: Nature Chemistry. 2011 ; Vol. 3, No. 2. pp. 167-171.
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