Iridium-catalyzed transfer hydrogenation of nitroarenes to anilines?

New Journal of Chemistry Pub Date: 2015-05-06 DOI: 10.1039/C5NJ00917K

Abstract

A simple and general homogeneous catalyst system composed of commercially available [Ir(cod)Cl]2 and 1,10-phenanthroline has been developed for the selective transfer hydrogenation of nitroarenes to anilines. It utilized the readily accessible 2-propanol as a hydrogen donor and had wide substrate scope. A careful mechanistic investigation through real-time detection and a series of controlled experiments with possible intermediates was also carried out, which showed that the transformation proceeds via both phenylhydroxylamine and azobenzene intermediates and the reduction of hydrazobenzene leading to aniline might be the rate-determining step.

Graphical abstract: Iridium-catalyzed transfer hydrogenation of nitroarenes to anilines
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