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学科主题: 氟化学
题名: From Olefination to Alkylation: In-Situ Halogenation of Julia-Kocienski Intermediates Leading to Formal Nucleophilic Iodo- and Bromodifluoromethylation of Carbonyl Compounds
其他题名: 从烯化到烷基化: 对Julia-Kocienski中间体的现场卤化实现了对羰基化合物的形式上亲核一碘二氟甲基化反应
作者: Zhao YC(赵延川) ; Gao B(高兵) ; Hu JB(胡金波)
通讯作者: 胡金波
刊名: J. Am. Chem. Soc.
发表日期: 2012
卷: 134, 期:13, 页:5790-5793
收录类别: SCI
部门归属: 中科院上海有机化学研究所
英文摘要: Iodo- and bromodifluoromethylated compounds are important synthetic intermediates and halogen-bond acceptors. However, direct introduction of -CF2I and -CF2Br groups through nucleophilic addition is particularly challenging because of the high tendency of decomposition of CF2Br- and CF2I- to difluorocarbene. In this work, we have developed a formal nucleophilic iodo- and bromodifluoromethylation for carbonyl compounds. The key strategy of the method is the halogenation of in situ-generated sulfinate intermediates from the Julia-Kocienski reaction to change the reaction pathway from the traditional olefination to alkylation. Interesting halogen-pi interactions between the halocarbon and aromatic donors were observed in the crystal structures of the products. The method could also be extended to the introduction of other fluorinated groups, such as -CFClBr, -CFClI, -CFBr2, and -CFMeI, which opens up new avenues for the synthesis of a wide range of useful fluorinated products.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000302490000019
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/28259
Appears in Collections:中科院有机氟化学重点实验室_期刊论文

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Recommended Citation:
Zhao YC,Gao B,Hu JB. From Olefination to Alkylation: In-Situ Halogenation of Julia-Kocienski Intermediates Leading to Formal Nucleophilic Iodo- and Bromodifluoromethylation of Carbonyl Compounds[J]. J. Am. Chem. Soc.,2012,134(13):5790-5793.
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