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Palladium-catalyzed sequential oxidative cyclization/coupling of 2-alkynylphenols and alkenes: a direct entry into 3-alkenylbenzofurans.

Authors
  • Martínez, Claudio
  • Alvarez, Rosana
  • Aurrecoechea, José M
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Mar 05, 2009
Volume
11
Issue
5
Pages
1083–1086
Identifiers
DOI: 10.1021/ol8028687
PMID: 19199489
Source
Medline
License
Unknown

Abstract

A new Pd-catalyzed tandem intramolecular oxypalladation/Heck-type coupling between 2-alkynylphenols and alkenes is reported, leading to 3-(1-alkenyl)benzofurans. Participating alkenes include those substituted with an electron-withdrawing group (ester, ketone, amide, nitrile, sulfone), as well as styrene. Remarkably, beta-substituted-alpha,beta-unsaturated carbonyl-type derivatives also participate effectively. The ready availability of substituted alkynylphenols, together with flexibility in the alkene choice, makes this simple strategy a versatile one for the synthesis of structurally diverse benzofuran derivatives.

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