Heterogeneously-catalyzed competitive hydroarylation/hydromination of norbornene with aniline in the presence of Aquivion® ionomer

Abstract

The hydroarylation of alkenes with aniline is a reaction of high interest, in particular for the manufacture of polyurethanes. This reaction has been mostly investigated in the presence of homogeneous catalysts. So far, heterogeneous catalysts have been scarcely reported for this reaction, mainly due to their inherent low activity and deactivation during the course of the reaction. Here we report the catalytic performance of Aquivion® ionomer, a perfluorinated solid acid polymer, in the hydroarylation of norbornene with aniline. We show that Aquivion® ionomer was robust and can be recycled for at least 6 runs without any decrease of its catalytic performances. Our results also highlight that Aquivion® ionomer improves the propensity of aniline to react through its aromatic ring, thus yielding a higher proportion of hydroarylation products as compared to other tested homogeneous and heterogeneous catalysts.