Metal-catalyzed phosphinyl ester forming reaction of alcohols and phenols with diphosphine disulfides and a dioxide

Mieko Arisawa, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

Transition metal complexes catalyzed the dialkylphosphinothioation reaction of alcohols and phenols with tetraalkyldiphosphine disulfides in high yields. Phenols were reacted in the presence of RhH(PPh3)4 and 1,2-bis(dimethylphosphino)ethane under THF reflux, and alcohols with Pd(OAc)2 and 1,2-bis(diphenylphosphino)benzene under chlorobenzene reflux. Primary alcohols reacted faster than secondary alcohols under these conditions, and protected tyrosine and serine were phosphinothioated with minimal racemization. Tetraphenyldiphosphine dioxide also underwent the P-O bond formation reaction.

Original languageEnglish
Pages (from-to)4840-4842
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number37
DOIs
Publication statusPublished - 2010 Sep 15

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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