Rhodium(II)-Catalyzed Transylidation of Aryliodonium Ylides: Electronic Effects of Aryl Groups Determine Their Thermodynamic Stabilities

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• 作者：Masahito Ochiai ; Takuya Okada ; Norihiro Tada ; Akira Yoshimura
• 刊名：Organic Letters
• 出版年：2008
• 出版时间：April 3, 2008
• 年：2008
• 卷：10
• 期：7
• 页码：1425 - 1428
• 全文大小：75K
• 年卷期：v.10,no.7(April 3, 2008)
• ISSN：1523-7052

文摘

Intermolecular transylidations between aryliodonium ylides under catalytic conditions were developed. Heating a solution of phenyliodoniumbis(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 aryliodoniumylide in a good yield. Reversible nature of the catalytic intermolecular transylidation makes it possible to evaluate the thermodynamic stabilityof aryliodonium ylides.