Iron(III)-catalysed nitration of non-activated and moderately activated arenes with nitrogen dioxide–molecular oxygen under neutral conditions

Abstract

In the presence of molecular oxygen and a catalytic amount of tris(pentane-2,4-dionato)iron(III), non-activated and moderately activated arenes, which include alkylbenzenes, halogenobenzenes, phenolic ethers, naphthalene and derivatives, can be nitrated with nitrogen dioxide at ice-bath temperature or below to give the corresponding nitro derivatives in fair to good yields. An electron-transfer mechanism has been proposed, where an activated NO₂-Fe^III complex plays a key role in the cyclic process for converting arenes into nitroarenes.