Rhodium(II)-catalyzed transylidation of aryliodonium ylides

Electronic effects of aryl groups determine their thermodynamic stabilities

Masahito Ochiai, Takuya Okada, Norihiro Tada, Akira Yoshimura

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

(Chemical Equation Presented) Intermolecular transylidations between aryliodonium ylides under catalytic conditions were developed. Heating a solution of phenyliodonium bis(trifluoromethylsulfonyl)methylide in a large amount (80 equiv) of a substituted iodobenzene in the presence of 5 mol % of rhodium(II) acetate as a catalyst transfers the bis(trifluoromethylsulfonyl)- methylidene group to the iodine(I) atom and affords a substituted aryliodonium ylide in a good yield. Reversible nature of the catalytic intermolecular transylidation makes it possible to evaluate the thermodynamic stability of aryliodonium ylides.

Original languageEnglish
Pages (from-to)1425-1428
Number of pages4
JournalOrganic Letters
Volume10
Issue number7
DOIs
Publication statusPublished - 3 Apr 2008
Externally publishedYes

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Rhodium
rhodium
Thermodynamics
Iodine
Heating
iodine
acetates
Acetates
Thermodynamic stability
catalysts
Atoms
thermodynamics
Catalysts
heating
electronics
atoms
phenyliodonium
iodobenzene

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Rhodium(II)-catalyzed transylidation of aryliodonium ylides : Electronic effects of aryl groups determine their thermodynamic stabilities. / Ochiai, Masahito; Okada, Takuya; Tada, Norihiro; Yoshimura, Akira.

In: Organic Letters, Vol. 10, No. 7, 03.04.2008, p. 1425-1428.

Research output: Contribution to journalArticle

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