Palladium-catalyzed synthesis of aryl-substituted polyamine compounds from aryl halides.

The reaction of polyamines having primary amino groups and 1,2-diaminoethane and/or 1,3-diaminopropane fragments with aryl bromides or iodides in the presence of sodium tert-butoxide and (dppf)PdCl2, (dppf=1,1'-bis(diphenylphosphino)ferrocene) proceeds selectively leading to monoaryl-substituted derivatives of polyamine. This reaction provides a convenient method of arylation of di-, tri- and tetraamine compounds. The Pd-catalyzed reactions of 1,3-diaminopropane and 3,3'-diaminodipropylamine with more reactive 1-bromonaphthalene can be used for the preparation of sym-dinaphthyl derivatives of these amines. (C) 1997 Published by Elsevier Science Ltd.