Author: ["Ritu Ahuja","Benudhar Punji","Michael Findlater","Carolyn Supplee","William Schinski","Maurice Brookhart","Alan S. Goldman"]
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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 ‘pincer’-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. Aromatic hydrocarbons are among the most important building blocks in the chemical industry. Here, n-alkanes are catalytically converted to alkylaromatics, in yields up to 86%, using ‘pincer’-ligated iridium complexes and olefinic hydrogen acceptors. The carbon number of the n-alkanes is retained in the products, which are exclusively unbranched (n-alkyl-substituted).Cite this article
Ahuja, R., Punji, B., Findlater, M. et al. Catalytic dehydroaromatization of n-alkanes by pincer-ligated iridium complexes. Nature Chem 3, 167–171 (2011). https://doi.org/10.1038/nchem.946 