Issue 1, 2010
From the journal:

Chemical Communications

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,a   David Tilly,a   Zhou Lia  and  Vladimir Gevorgyan*a  

* Corresponding authors

a Department of Chemistry, University of Illinois, 845 West Taylor Street, Chicago, USA
E-mail: vlad@uic.edu
Fax: (+1)-312 996 0431
Tel: (+1)-312-355-3579

Abstract

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

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Article information

DOI
https://doi.org/10.1039/B919991H
Article type
Communication
Submitted
25 Sep 2009
Accepted
27 Oct 2009
First published
17 Nov 2009

Chem. Commun., 2010,46, 150-152

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

N. Chernyak, D. Tilly, Z. Li and V. Gevorgyan, Chem. Commun., 2010, 46, 150 DOI: 10.1039/B919991H

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