One-pot Chemoselective Reductive Alkylation of Nitroarenes: a New and General Method of Synthesis of Alkylanilines

A New facile and general synthesis of alkylanilines by one-pot reductive alkylation of nitroarenes is reported. This method is based on the “in situ” reduction by hydrides (LiAlH4 or NaBH4) in the presence of catalytic amounts of PdC, of nitronate adducts arising from the conjugate addition of Grignard reagents to mononitroarenes. LiAlH4 showed to be a more efficient but less selective reducing agent than NaBH4. The reaction can be successfully applied to mono, homo and hetero bicyclic systems and allows to introduce a large variety of alkyl chains without isomerisation phenomena