The use of abundant and inexpensive iron catalysts to mediate various organic transformations has garnered much interest in recent years in an attempt to replace the more-widely employed precious metal systems. Indeed, iron catalysts have been employed as viable alternatives for palladium in classic cross-coupling reactions and other well-studied transformations. The air-stable [Fe(salen)]2-μ-oxo catalysts have been employed as effective precatalysts for the hydrophosphination and cyclopropanation of olefins as well as the oxidative coupling of phenol derivatives. Catalysis from these species can be envisaged to proceed via a range of readily-generated active catalysts, conferring a multitude of potential mechanistic pathways. We recently reported an alkyne trimerisation procedure catalysed by [Fe(salen)]2-μ-oxo and HBpin which was hypothesised to proceed via a unique [FeH(salen)]Bpin species. We have also utilised the catalytic pairing of [Fe(salen)]2-μ-oxo and HBpin for the hydroboration of carbonyl derivatives. Herein we report the use of this catalytic pair once again in the reduction of nitro-organics and endeavour to fully elucidate the mechanistic pathway utilising various spectroscopic techniques and complementary computational data.

Understanding the mechanism of organic transformations mediated by [Fe(salen)]2-μ-oxo precatalysts

ACS Spring 2022

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