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学科主题: 氟化学 ; 金属有机化学
题名: Palladium(0)/Copper(I)-cocatalyzed cross-coupling of the zinc reagent of ethyl 3-bromo-3,3,-difluoropropionate with aryl (Alkenyl) halides:An efficient stereoselective synthesis of β-fluoro-α,β-unsaturated esters.
其他题名: 钯(0)铜(I)催化3-溴-3,3-亚氟丙酸乙酯的锌试剂与芳基卤化物的偶联反应: 立体选择合成β-氟α,β-不饱和酯的有效方法
作者: Peng S(彭晟) ; Qing FL(卿凤翎) ; Li YQ(李毅群) ; Hu CM(胡昌明)
通讯作者: 卿凤翎
刊名: J. Org. Chem.
发表日期: 2000-01-01
卷: 65, 期:3, 页:694-700
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所氟有机化学开放实验室
英文摘要: Ethyl S-bromo-3, 3-diFluoropropionate (1) was prepared in an overall yield of 75% from the radical addition of dibromodifluoromethane to ethyl vinyl ether under Na^2^s20^4 initiation, followed by oxidation of the acetal with CaEo~acid. The treatment of 1 with active zinc dust in anhydrous DMF at room temperature produced the zinc reagent ZnBrCF^2CH^2CO^2C^2H^5 (2). The cross coupling of the zinc reagent 2 with aryl (alkenyl) halides (R-X) in DM7 using Pd(0)- Cu(I) as cocatalyst stereoselectively provided the β-fluoro-α,β-unsaturated esters (RCF=CHCO^2C^2H^5 4) directly and in moderate yields. An E/Z ratio ranging from 3:2 to 1:0 was observed. This is the first example that Cu(I) can improve the selectivity of the cross-coupling reaction. Mechanistic studies revealed that zinc reagent 2 underwent stereoselective elimination to produce (Z)- 1-fluoro-2-(ethoxycarbonyl)-ethenylzinc reagent 6, and then the cross-coupling of 6 with aryl(alkenyl) halides under palladium-(0) catalysis afforded the β-f1uoro-α,β-unsaturated esters 4.
语种: 英语
相关网址: 查看原文
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/17459
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:
Peng S,Qing FL,Li YQ,et al. Palladium(0)/Copper(I)-cocatalyzed cross-coupling of the zinc reagent of ethyl 3-bromo-3,3,-difluoropropionate with aryl (Alkenyl) halides:An efficient stereoselective synthesis of β-fluoro-α,β-unsaturated esters.[J]. J. Org. Chem.,2000,65(3):694-700.
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