Synthesis of alkyl 2,5-dihydro-5-oxofuran-2-carboxylates via palladium-catalyzed carbonylative cyclization of β-bromovinyl aldehydes in alcohols

Chan Sik Cho, Jun Uk Kim, Heung Jin Choi

Research output: Contribution to journalShort surveypeer-review

30 Scopus citations

Abstract

β-Bromovinyl aldehydes reacts with carbon monoxide and alcohols at 125 °C in the presence of a catalytic amount of a palladium catalyst along with a base to give the corresponding carbonylative cyclized alkyl 2,5-dihydro-5-oxofuran-2-carboxylates in good yields. A reaction pathway involving intramolecular addition of acylpalladium to formyl group is proposed as a key step of this catalytic process.

Original languageEnglish
Pages (from-to)3677-3680
Number of pages4
JournalJournal of Organometallic Chemistry
Volume693
Issue number24
DOIs
StatePublished - 15 Nov 2008

Keywords

  • β-Bromovinyl aldehydes
  • Alcohols
  • Carbon monoxide
  • Carbonylative cyclization
  • Lactones
  • Palladium catalyst

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