One-pot preparation of azobenzenes from nitrobenzenes by the combination of an indium-catalyzed reductive coupling and a subsequent oxidation

We demonstrated how a reduction step with a reducing system comprised of In(OTf)(3) and Et3SiH and a subsequent oxidation that occurred under an ambient (oxygen) atmosphere allowed the highly selective and catalytic conversion of aromatic nitro compounds into symmetrical or unsymmetrical azobenzene derivatives. This catalytic system displayed a tolerance for the functional groups on a benzene ring: an alkyl group, a halogen, an acetyl group, an ester, a nitrile group, an acetyl group, an ester moiety, and a sulfonamide group. (C) 2014 Elsevier Ltd. All rights reserved.