Infrared irradiation assisted both the synthesis of ( Z)-(aminomethyl)(aryl)phenylhydrazones via the Mannich coupling reaction and their application to the palladium-catalyzed Heck reaction

Abstract

The Mannich coupling reaction between arylhydrazones, formaldehyde and a secondary amine to generate the ( Z)-(aminomethyl)(aryl)phenylhydrazones 1a–h assisted by infrared irradiation (IR) under solvent-free conditions is herein reported, and the catalytic potential of compounds 1a–h in the palladium-catalyzed and IR-assisted Heck coupling reaction is also evaluated. Coupling products are obtained in high yields and short reaction times. We show the advantages of this new alternative to promote both Mannich and Heck coupling reactions.