Palladium nanoparticle catalyzed synthesis of indoles via intramolecular Heck cyclisation
Debasish Sarmah1,2, Anup Choudhury3, Utpal Bora1
1Dept of Chemical Sciences, Tezpur University, Napam, Sonitpur, Assam, India. ubora@tezu.ernet.in.
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.
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