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学科主题: 氟化学
题名: Copper-Mediated Fluoroalkylation Reactions with Iododifluoroacetamides: Controlling the Selectivity among Cross-Coupling, Intramolecular Cyclization, and Homocoupling Reactions
其他题名: 单质铜参与的利用一碘二氟乙酰胺进行氟烷基化反应: 控制交叉偶联、分子内成环、自偶联反应之间的选择性
作者: Zhu JM(朱杰明) ; Zhang W(张伟) ; Zhang LJ(张来俊) ; Liu J(刘俊) ; Zheng J(郑吉) ; Hu JB(胡金波)
通讯作者: 胡金波
刊名: J. Org. Chem.
发表日期: 2010
卷: 75, 期:16, 页:5505-5512
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所
英文摘要: Cu-mediated fluoroalkylation reactions with iododifluoroacetamides I have been systematically investigated. It was found that three types of reactions may coexist in Cu-mediated reactions between iododifluoroacetamides and aryl/alkenyl iodides: cross-coupling, intramolecular cyclization, and homocoupling reactions. The selectivity among these three types of reactions could be controlled by tuning the substituents on the nitrogen atom of iododifluoroacetamides, and/or by removing the cross-coupling reaction partner (aryl/alkenyl halides). The general rule is as follows: (a) in the presence of proper aryl/alkenyl iodides, the cross-coupling products 2 (or 6) are generally formed as the major products; (b) in the absence of aryl/alkenyl iodides, and when R-1 = alkyl and R-2 = aryl groups, or when R-1 = R-2 = aryl groups, the intramolecular cyclization products 3 can be formed predominantly; and (c) in the absence of aryl/alkenyl iodides, and when R-1 = R-2 = alkyl groups, or when R-1 = H and R-2 = alkyl, aryl groups, the homocoupling products 4 can be formed dominantly. Our experimental results also indicate that in many cases when cross-coupling, homocoupling, and intramolecular cyclization reactions coexist in the Cu-mediated reaction system, the reactivity decreases in the following order: cross-coupling > intramolecular cyclization > homocoupling.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000280798900009
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/24069
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:
Zhu JM,Zhang W,Zhang LJ,et al. Copper-Mediated Fluoroalkylation Reactions with Iododifluoroacetamides: Controlling the Selectivity among Cross-Coupling, Intramolecular Cyclization, and Homocoupling Reactions[J]. J. Org. Chem.,2010,75(16):5505-5512.
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