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

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 oxida...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2006-01, Vol.4 (7), p.1213-1216
Main Authors: Fairlamb, Ian J S, O'Brien, Ciara T, Lin, Zhenyang, Lam, King Chung
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Kinetics
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Conformation
Pyrones - chemistry
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/b518232h