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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
Zhao YC(赵延川); Gao B(高兵); Hu JB(胡金波)
2012
发表期刊J. Am. Chem. Soc.
ISSN0002-7863
卷号134期号:13页码:5790-5793
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.
学科领域氟化学
部门归属中科院上海有机化学研究所
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收录类别SCI
语种英语
WOS记录号WOS:000302490000019
引用统计
被引频次:52[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/28259
专题中科院有机氟化学重点实验室
通讯作者Hu JB(胡金波)
推荐引用方式
GB/T 7714
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.
APA 赵延川,高兵,&胡金波.(2012).From Olefination to Alkylation: In-Situ Halogenation of Julia-Kocienski Intermediates Leading to Formal Nucleophilic Iodo- and Bromodifluoromethylation of Carbonyl Compounds.J. Am. Chem. Soc.,134(13),5790-5793.
MLA 赵延川,et al."From Olefination to Alkylation: In-Situ Halogenation of Julia-Kocienski Intermediates Leading to Formal Nucleophilic Iodo- and Bromodifluoromethylation of Carbonyl Compounds".J. Am. Chem. Soc. 134.13(2012):5790-5793.
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