Chromatography-free Pd-catalyzed deprotection of allyl ethers using PS-DEAM as a scavenger of boronic acids and Pd catalyst

Hirokazu Tsukamoto, Takamichi Suzuki, Masanori Sato, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Polystyrene-bound diethanolamine (PS-DEAM) work-up for a newly developed Pd(PPh3)4-catalyzed cleavage of allylic alkyl ethers using phenylboronic acid can effectively release Pd-free parent alcohols. Furthermore, chromatography-free deallylation can be conducted by using vinylboronic anhydride pyridine complex as an allyl scavenger with a catalytic amount of Pd(OAc)2 and 4-(diphenylphosphino)benzoic acid instead of Pd(PPh3)4 to yield the desired products in high purities and yields after removal of volatile byproducts and the phosphine-derived contaminants by evaporation and sequestration through acid-base interaction with PS-DEAM, respectively.

Original languageEnglish
Pages (from-to)8438-8441
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number48
DOIs
Publication statusPublished - 2007 Nov 26

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Chromatography-free Pd-catalyzed deprotection of allyl ethers using PS-DEAM as a scavenger of boronic acids and Pd catalyst'. Together they form a unique fingerprint.

Cite this