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学科主题: 氟化学 ; 金属有机化学
题名: 钯催化下(Z)-3-碘-3-三氟甲基-1-芳基丙醇与末端炔烃的偶联反应
其他题名: Palladium-catalyzed cross-coupling of (Z)-3-Iodo-3-trifluoromethyl-1-aryl allylic alcohols with terminal alkynes
作者: 卿凤翎 ; 高文忠
通讯作者: 卿凤翎
刊名: 有机化学
发表日期: 2000-01-01
卷: 20, 期:5, 页:764-768
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
摘要: 在Pd(PPh^3)^4/CuI 催化下和使用 1 mol 的Net^3 作碱和 THF 作溶剂, (Z)-3-碘-3-三氟甲基-1-芳基丙醇(1)与末端炔烃(3)反应得到正常的偶联产物 5。当以 Net^3作碱和溶剂, Pd(PPh^3)^4/CuI催化1与3的交叉偶联反应生成化合物4。4为正常偶联化合物5在NE^3存在下双键发生重排反应的产物。
英文摘要: The direct reaction of two equivalents of lithium diisopropylamide (LDA) with 2-bromo-3,3,3-trifluoropropene gave lithium trifluoromethylacetylide, which was then trapped with aromatic aldehydes to produce trifluoromethyl propargyl alcohols (2) in high yields. Treatment of 2 with LiAlH^4 and followed by I^2 provided (Z)-3-iodo-3-trifluoromethyl-1-aryl allylic alcohols (1). In the presence of 1 equivalent of triethylamine, Pd(PPh^3)^4/CuI catalyzed cross-coupling of 1 with teminal alkynes in THF at 50℃ afforded conjugated (E)-3-alkynyl-3-trifluoromethyl allylic alcohols 5. When triethylamine was used as both base and solvent, the Pd(PPh^3)^4/CuI catalyzed crosscoupling of 1 with terminal alkynes led to ketones 4 instead of the expected 5. Mechanistic studies revealed that 5 was easily rearranged to 4 in the presence of triethylamine.
语种: 中文
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/17463
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:
卿凤翎,高文忠. 钯催化下(Z)-3-碘-3-三氟甲基-1-芳基丙醇与末端炔烃的偶联反应[J]. 有机化学,2000,20(5):764-768.
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