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

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/B919991H
Article type
Communication
Submitted
25 9 2009
Accepted
27 10 2009
First published
17 11 2009

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

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements