Copper-catalyzed anti-hydrophosphination reaction of 1-alkynylphosphines with diphenylphosphine providing (Z)-1,2-diphosphino-1-alkenes

Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima

Research output: Contribution to journalArticlepeer-review

86 Citations (Scopus)

Abstract

Hydrophosphination of 1-alkynylphosphines with diphenylphosphine proceeds in an anti fashion under copper catalysis, providing an easy and efficient access to a variety of (Z)-1,2-diphosphino-1-alkenes and their sulfides. The reaction is highly chemoselective and can be performed even in an aqueous medium. The reaction is reliable enough to realize a gram-scale synthesis of (Z)-1,2-diphosphino-1-alkene. Radical reduction of the diphosphine disulfides with tris(trimethylsilyl)silane yields the parent trivalent diphosphines without suffering from the isomerization of the olefinic geometry. Enantioselective hydrogenation of (Z)-3,3-dimethyl-1,2-bis(diphenylthiophosphinyl)-1-butene followed by desulfidation leads to a new chiral bidentate phosphine ligand.

Original languageEnglish
Pages (from-to)4099-4104
Number of pages6
JournalJournal of the American Chemical Society
Volume129
Issue number13
DOIs
Publication statusPublished - 2007 Apr 4
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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