Palladium(0)-catalyzed [4+2] Annulation of Salicylaldehydes and Propargyl Carbonates to Produce 3,4-Dihydro-2-methylene-2H-1-benzopyran-4-ols

Ayumu Kawase, Hirotaka Omura, Takayuki Doi, Hirokazu Tsukamoto

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Palladium(0)-catalyzed synthesis of 3,4-dihydro-2-methyl-ene-2H-1-benzopyran-4-ols via annulation between salicylaldehyde and propargyl carbonate using a formate reductant is reported herein. The annulation proceeds via common addition of the hydroxyl group in salicylaldehyde to the central carbon of η3-allenyl-/propargylpalladium, wherein the latter is generated through the oxidative addition of propargyl carbonate to the catalyst and subsequent intramolecular umpolung allylation of the aldehyde.

Original languageEnglish
Pages (from-to)1402-1405
Number of pages4
JournalChemistry Letters
Volume48
Issue number11
DOIs
Publication statusPublished - 2019

Keywords

  • Propargyl carbonate
  • Salicylaldehyde
  • [4+2] Umpolung annulation

ASJC Scopus subject areas

  • Chemistry(all)

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