Palladium-catalyzed tandem dimerization and cyclization of acetylenic ketones: A convenient method for 3,3 '-bifurans using PdCl2(PPh3)(2)

Authors
Jeevanandam, A Narkunan, K Ling, YC
Citation
A. Jeevanandam et al., Palladium-catalyzed tandem dimerization and cyclization of acetylenic ketones: A convenient method for 3,3 '-bifurans using PdCl2(PPh3)(2), J ORG CHEM, 66(18), 2001, pp. 6014-6020
Citations number
42
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
18
Year of publication
2001
Pages
6014 - 6020
Database
ISI
SICI code
0022-3263(20010907)66:18<6014:PTDACO>2.0.ZU;2-R
Abstract
Alkynones undergo tandem dimerization and cyclization in the presence of Pd Cl2(PPh3)(2) and triethylamine in tetrahydrofuran at room temperature to gi ve 3,3 ' -bifurans predominantly. Other palladium catalysts while under sim ilar conditions, by rearrangement, lead to 2,5-disubstituted furans. This d istinguished property of PdCl2(PPh3)(2) has been attributed to the involvem ent of hydridopalladium. halide. This method provides a simpler route to a variety of furans and a regioselective synthesis of polysubstituted 3,3 ' - bifurans using easily accessible acetylenic ketones.