SYNTHESIS OF 3-HYDROXYALKYLBENZO[B]FURANS VIA THE PALLADIUM-CATALYZEDHETEROANNULATION OF SILYL-PROTECTED ALKYNOLS WITH 2-IODOPHENOL

Authors
BISHOP BC COTTRELL IF HANDS D
Citation
Bc. Bishop et al., SYNTHESIS OF 3-HYDROXYALKYLBENZO[B]FURANS VIA THE PALLADIUM-CATALYZEDHETEROANNULATION OF SILYL-PROTECTED ALKYNOLS WITH 2-IODOPHENOL, Synthesis, (11), 1997, pp. 1315-1320
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
11
Year of publication
1997
Pages
1315 - 1320
Database
ISI
SICI code
0039-7881(1997):11<1315:SO3VTP>2.0.ZU;2-A
Abstract
The palladium-catalysed annulation of silyl-protected alkynols with 2- iodophenol gives silyl-protected 3-hydroxyalkylbenzo[b]furans 3 a-I. T he use of silyl-protected propynols bearing a free hydroxyl or an O-tr iethylsilyl protecting group resulted in the formation of 1-oxa-2-sila cyclopent-3-enes 5a-d as the major products. Removal of the silyl prot ecting groups from silyl benzo[b]furans 3c,3e and 3i affords 3-hydroxy alkylbenzo[b]furans 9a-c in good yield.