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 oxidative addition is favoured both kinetically and thermodynamically.
Department of Chemistry, University of York, Heslington, York, UK YO10 5DD. ijsf1@york.ac.uk
Ian J S
IJ
Fairlamb
Ciara T
CT
O'Brien
Zhenyang
Z
Lin
King Chung
KC
Lam
D000480:Alkynes / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D011753:Pyrones / Q000737:chemistry*
D000480:Alkynes; D011753:Pyrones