Rhodium(II)-catalyzed transylidation of aryliodonium ylides: electronic effects of aryl groups determine their thermodynamic stabilities.
Rhodium(II)-catalyzed transylidation of aryliodonium ylides: electronic effects of aryl groups determine their thermodynamic stabilities.
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DOI：
10.1021/ol800211x
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发表时间：
2008-02
期刊：
影响因子：
5.2
通讯作者：
M. Ochiai;T. Okada;N. Tada;A. Yoshimura
中科院分区：
文献类型：
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作者：
M. Ochiai;T. Okada;N. Tada;A. Yoshimura
研究了芳基碘叶立德在催化条件下的分子间转磺基化反应。在5mol%乙酸铑（II）作为催化剂的存在下，加热苯基碘鎓双（三氟甲基磺酰基）亚甲基在大量（80当量）取代碘苯中的溶液，将双（三氟甲基磺酰基）亚甲基转移到碘（I）原子上，以良好的产率得到取代的芳基碘鎓叶立德。催化的分子间转磺基化反应的可逆性使得评价芳基碘叶立德的热力学稳定性成为可能。
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.