Synthesis of bulky arylphosphanes by rhodium-catalyzed formal [2+2+2] cycloaddition reaction and their use as ligands

Takayuki Kobatake, Azusa Kondoh, Suguru Yoshida, Hideki Yorimitsu, Koichiro Oshima

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Treatment of 1-alkynylphosphane sulfides with 1,6- or 1,7-diynes in the presence of a cationic rhodium catalyst results in a formal [2+2+2] cycloaddition reaction to afford the corresponding aromatic phosphane sulfides. The aromatic rings formed in the cycloaddition naturally bear one or two substituents at the ortho positions to the phosphorus atom, which creates a sterically hindered environment around the phosphorus atom. The following desulfidation of the products is facile under radical conditions or with the aid of tris(dimethylamino)phosphane, providing the corresponding bulky phosphanes. Dicyclohexyl(2,6-diphenylaryl)-phosphane, which is available through this sequence, proves to serve as an efficient ligand in palladium-catalyzed cross-coupling amination reactions.

Original languageEnglish
Pages (from-to)1613-1619
Number of pages7
JournalChemistry - An Asian Journal
Volume3
Issue number8-9
DOIs
Publication statusPublished - 2008 Sep 1
Externally publishedYes

Keywords

  • Amination
  • Cross-coupling
  • Cycloaddition
  • Phosphanes
  • Rhodium

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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