Iron(ii)-catalyzed intermolecular aziridination of alkenes employing hydroxylamine derivatives as clean nitrene sources

Abstract

The iron-catalyzed intermolecular aziridination of alkenes with hydroxylamine derivatives is described. Using simple iron(II) sources and readily available ligands, the formal (2 + 1) cycloaddition process proved to be efficient on both styrenes and aliphatic alkenes, providing access to a wide range of aziridines. In these particularly sustainable reaction conditions, yields up to 89% could be obtained, with a catalyst loading which could be lowered to 5 mol% when the reaction was performed on large scale. Preliminary mechanistic studies suggest that both concerted and stepwise pathways are operating in this transformation.