Copper catalyzed Gomberg-Buchmann-Hey reaction using aryldiazonium tosylate

Copper catalyzed modification of Gomberg-Bachmann-Hey reaction to synthesize symmetrical/unsymmetrical biaryls via diazotization of anilines with p-TSA and NaNO2 system at 50 degrees C, in aromatic liquids as solvents and second partners was successfully developed. Aniline and 3-nitronaniline gave biphenyl and 3-nitrobiphenyl, respectively, with moderate yields. All para-substituted anilines gave comparatively higher yields while in the other cases including ortho-substituted anilines yields were lower. Except anilines with o-NHCOCH3 and o-CONH2 which gave symmetrical biaryls, all others gave selectively unsymmetrical biaryls. (C) 2011 Elsevier Ltd. All rights reserved.