In developing low temperature synthetic routes for benzene, toluene, and xylene, some of the most important building blocks of the chemical industry, we recently reported the first example of homogeneous catalytic dehydroaromatization of n-alkanes via pincer-ligated iridium catalysts.  For n-alkanes with C=10, the reaction primarily yields linear alkylbenzenes with conservation of the entire carbon chain, but a surprisingly significant yield of benzene is observed for C=11. Herein, we report a retro-ene fragmentation mechanism, which is a rearrangement akin to a 1,5-hydrogen shift, that explains the presence of benzene. We also report that the product distribution can be altered with the use of a combination of different pincer-ligated iridium catalysts, each chosen for a specific role. For example, the ratio of monoalkylbenzenes to dialkylbenzenes can be increased from 1:4 to 1:1.

Catalytic dehydroaromatization of <i>n</i>-alkanes: Toward a mechanistic understanding and control of product distribution

245th National Meeting (2013)

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Catalytic dehydroaromatization of n-alkanes: Toward a mechanistic understanding and control of product distribution