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Chem. Commun., 2010, 46, 150 - 152, DOI: 10.1039/b919991h

Pd-catalyzed cascade carbopalladation-annulation reaction of 3-(2-iodobenzyl)-indoles into fused 6/5/7/6- and 6/5/5/6- heterocyclic systems

Natalia Chernyak, David Tilly, Zhou Li and Vladimir Gevorgyan

Polycyclic indole structures, possessing fused seven-membered rings were efficiently synthesized via the Pd-catalyzed intramolecular carbopalladation-annulation of 3-(2-iodobenzyl)-indoles and alkynes. A remarkable base effect on the chemoselectivity of this transformation has been found: switching from Et3N to CsOAc completely reverses the reaction path to intramolecular cyclization forming fused five-membered rings.

Graphical abstract image for this article (ID: b919991h)