Linear alkylbenzenes are widely used as precursors for detergents and surfactants and are primarily synthesized by arene-olefin coupling reactions. Accessing linear alkylbenzenes from alkane starting materials would be desirable in that alkanes are less costly than either arenes or olefins. We have recently reported the dehydroaromatization of n-alkanes to give alkylbenzenes, catalyzed by pincer-ligated iridium complexes. These are the first examples of dehydroaromatization in which the carbon number of higher (C>9) n-alkanes is largely retained in the formation of alkylbenzenes, although a significant degree of fragmentation occurs to give, surprisingly, benzene. In addition to the advantage of an inexpensive single feedstock, this represents a unique route to unbranched (n-alkyl) arenes that cannot be obtained through alkyation with olefins. The formation of benzene and efforts to control the product distribution will be discussed.                                                         

Catalytic dehydroaromatization of n-alkanes to form linear alkylbenzenes by pincer-ligated iridium complexes

244th National Meeting (2012)

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