Equilibrium shift in the rhodium-catalyzed acyl transfer reactions

Mieko Arisawa, Yui Igarashi, Haruki Kobayashi, Toru Yamada, Kentaro Bando, Takuya Ichikawa, Masahiko Yamaguchi

研究成果: Article査読

37 被引用数 (Scopus)

抄録

Rhodium/phosphine complexes catalyze equilibrium acyl transfer reactions between acid fluorides, aryl esters, acylphosphine sulfides, and thioesters. The use of appropriate co-substrates to accept heteroatom groups shifted the equilibrium to desired products. Acylphosphine sulfides and aryl esters were converted to acid fluorides using benzoylpentafluorobenzene as the fluoride donor, and the fluorination reaction of thioesters employed (4-tolylthio) pentafluorobenzene. Acid fluorides were converted into acylphosphine sulfides and thioesters using diphosphine disulfides and disulfides/triphenylphosphine, respectively. Aryl esters were obtained from acid fluorides and phenols in the presence of triphenylsilane. Aryl esters, acylphosphine sulfides, and thioesters were also interconverted in the presence of rhodium complexes. These rhodium-catalyzed acyl transfer reactions proceeded under neutral conditions without using acid or base. The involvement of acyl rhodium intermediates in these reactions was suggested by the carbothiolation reaction of thioesters and alkynes.

本文言語English
ページ(範囲)7846-7859
ページ数14
ジャーナルTetrahedron
67
40
DOI
出版ステータスPublished - 2011 10 7

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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