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

Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima

研究成果: Article査読

87 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)4099-4104
ページ数6
ジャーナルJournal of the American Chemical Society
129
13
DOI
出版ステータスPublished - 2007 4 4
外部発表はい

ASJC Scopus subject areas

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

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