Issue 7, 2006
From the journal:

Organic & Biomolecular Chemistry

Regioselectivity in the Sonogashira coupling of 4,6-dichloro-2-pyrone†

Ian J. S. Fairlamb,*a   Ciara T. O'Brien,a   Zhenyang Linb  and  King Chung Lamb  

* Corresponding authors

a Department of Chemistry, University of York, Heslington, York, UK
E-mail: ijsf1@york.ac.uk
Fax: +44 1904 432516
Tel: +44 1904 434091

b Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, P. R. China

Abstract

The Sonogashira cross-coupling of 4,6-dichloro-2-pyrone with terminal acetylenes proceeds in good yields and high regioselectivity for the 6-position; dibenzylidene acetone (dba) type ligands play a non-innocent role in reactions mediated by Pd(dba)2/PPh3; theoretical studies indicate that C-6 oxidative addition is favoured both kinetically and thermodynamically.

Graphical abstract: Regioselectivity in the Sonogashira coupling of 4,6-dichloro-2-pyrone

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Article information

DOI
https://doi.org/10.1039/B518232H
Article type
Communication
Submitted
22 Dec 2005
Accepted
02 Feb 2006
First published
21 Feb 2006

Org. Biomol. Chem., 2006,4, 1213-1216

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Regioselectivity in the Sonogashira coupling of 4,6-dichloro-2-pyrone

I. J. S. Fairlamb, C. T. O'Brien, Z. Lin and K. C. Lam, Org. Biomol. Chem., 2006, 4, 1213 DOI: 10.1039/B518232H

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