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Synthesis 1997; 1997(11): 1315-1320
DOI: 10.1055/s-1997-1357
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Synthesis of 3-Hydroxyalkylbenzo[b]furans via the Palladium-Catalysed Heteroannulation of Silyl-Protected Alkynols with 2-Iodophenol

Brian C. Bishop* , Ian F. Cottrell, David Hands
  • *Merck Sharp and Dohme Research Laboratories, Hertford Road, Hoddesdon, Hertfordshire, EN11 9BU, England, Fax +44(1992)470437
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Publication Date:
31 December 2000 (online)

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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.

3-hydroxyalkylbenzo[b]furan - palladium-catalysed heteroannulation

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