Remarkable solvent effect on Pd(0)-catalyzed deprotection of allyl ethers using barbituric acid derivatives: Application to selective and successive removal of allyl, methallyl, and prenyl ethers

Hirokazu Tsukamoto, Takamichi Suzuki, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

Pd(0)-catalyzed deprotection of allyl ethers using barbituric acid derivatives in protic polar solvent such as MeOH and aqueous 1,4-dioxane proceeds at room temperature without affecting a wide variety of functional groups. Control of the reaction temperature allows selective and successive cleavage of allyl, methallyl, and prenyl ethers. A study of ligand effects on the deprotection reveals that the improved reactivity in MeOH results from the accelerated oxidative addition to Pd(O).

Original languageEnglish
Pages (from-to)3131-3136
Number of pages6
JournalSynlett
Issue number20
DOIs
Publication statusPublished - 2007 Dec 17

Keywords

  • Allyl ethers
  • Barbituric acid
  • Methallyl ethers
  • Pd(0)-catalyzed deprotection
  • Prenyl ethers
  • Protic polar solvent

ASJC Scopus subject areas

  • Organic Chemistry

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