Palladium nanoparticle catalyzed synthesis of indoles via intramolecular Heck cyclisation

Abstract

A system utilizing palladium(II)-PEG has been devised for the intramolecular Heck cyclization of N-vinyl and N-allyl-2-haloanilines. The synthesis of a variety of indoles, including 2,3-diester substituted ones and 3-methyl indoles, has been accomplished using this catalytic system. The N-vinyl starting materials are obtained by the aza-Michael addition of 2-haloanilines with alkynecarboxylate esters, which, upon cyclization, yield ester-substituted indoles. Conversely, N-allyl-2-haloanilines yield 3-methylated indoles as the major products. The high activity of the system is owed to the in situ generation of Pd nanoparticles.