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Synthesis of 3-Hydroxyalkylbenzo[b]furans via the Palladium-Catalysed Heteroannulation of Silyl-Protected Alkynols with 2-Iodophenol
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1997
Year
Chemical EngineeringSilyl-protected AlkynolsEngineeringCross-coupling ReactionOrganic ChemistryOrganometallic CatalysisCatalysisChemistryPalladium-catalysed HeteroannulationO-triethylsilyl Protecting GroupHeterocycle ChemistrySynthetic ChemistrySilyl-protected Propynols
The palladium-catalysed annulation of silyl-protected alkynols with 2-iodophenol gives silyl-protected 3-hyddroxyalkylbenzo[b]furans 3a-l. The use of silyl-protected propynols bearing a free hydroxyl or an O-triethylsilyl protecting group resulted in the formation of 1-oxa-2-silacyclopent-3-enes 5a-d as the major products. Removal of the silyl protecting groups from silyl benzo[b]urans 3c, 3e and 3i affords 3-hydroxyalkylbenzo[b]furans 9a-c in good yield.