Rhodium(II)-catalyzed transylidation of aryliodonium ylides: Electronic effects of aryl groups determine their thermodynamic stabilities

Masahito Ochiai, Takuya Okada, Norihiro Tada, Akira Yoshimura

Результат исследований: Материалы для журналаСтатья

15 Цитирования (Scopus)

Выдержка

(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.

Язык оригиналаАнглийский
Страницы (с-по)1425-1428
Число страниц4
ЖурналOrganic Letters
Том10
Номер выпуска7
DOI
СостояниеОпубликовано - 3 апр 2008
Опубликовано для внешнего пользованияДа

Отпечаток

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

Цитировать

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

В: Organic Letters, Том 10, № 7, 03.04.2008, стр. 1425-1428.

Результат исследований: Материалы для журналаСтатья

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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.",
author = "Masahito Ochiai and Takuya Okada and Norihiro Tada and Akira Yoshimura",
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T1 - Rhodium(II)-catalyzed transylidation of aryliodonium ylides

T2 - Electronic effects of aryl groups determine their thermodynamic stabilities

AU - Ochiai, Masahito

AU - Okada, Takuya

AU - Tada, Norihiro

AU - Yoshimura, Akira

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AB - (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.

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