4.8 Article

Efficient and Connective Assembly of Highly Functionalized Benzofurans Using o-Hydroxyphenones and Dichloroethylene

Journal

ORGANIC LETTERS
Volume 14, Issue 5, Pages 1298-1301

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol300186s

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Funding

  1. Universite catholique de Louvain (UCL)
  2. Fonds pour la formation a la Recherche dans l'Industrie et dans l'Agriculture (F.R.I.A.)
  3. Action de Recherches Concertees (ARC) [08/13-012]

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The preparation of highly functionalized benzofurans by a unique and connective transformation is reported. Base-catalyzed condensation of o-hydroxyphenones with 1,1-dichloroethylene generates the corresponding chloromethylene furans. These labile intermediates undergo a facile rearrangement into benzofuran carbaldehydes under mild acidic conditions.

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