The organometallic-catalyzed formation of a C-C bond via dehydrogenative coupling of two C-H bonds has been a target of intense interest in recent years, and several catalytic systems have been developed for this purpose. 1,4-Diarylbuta-1,3-diene is an important structural unit of natural products and pharmaceutical synthesis, and is of interest in the context of liquid crystals and non-linear optical materials. While in principle this unit can be synthesized via dehydrogenative coupling of two molecules of styrene or derivatives, no successful examples of such a transformation have been previously reported. Here we report the direct tail-to-tail dehydrogenative coupling of styrene to synthesize 1,4-diarylbuta-1,3-diene, using a pincer-iridium complex as catalyst, with styrene functioning as both the monomeric reactant and the hydrogen acceptor. The mechanism of the reaction has been studied by both experimental and computational methods.

Tail-to-tail dimerization of styrene via dehydrogenative coupling of styrene C-H bonds by a pincer iridium complex

252nd National Meeting (2016)

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