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新型离子液体的合成及其在Heck反应合成烯丙醇类化合物中的应用
引用本文:孙莉,陶荣哨,胡卫雅,裴文.新型离子液体的合成及其在Heck反应合成烯丙醇类化合物中的应用[J].合成化学,2015,23(10):899-903.
作者姓名:孙莉  陶荣哨  胡卫雅  裴文
作者单位:浙江工业大学 化学工程与材料学院,浙江 杭州 310014
基金项目:浙江省公益性技术应用研究计划资助项目(2012C21115)
摘    要:以甲基咪唑(或咪唑)和N-取代芳基-3-氯丙酰胺为原料,与KPF-6经离子交换制得6个新型酰胺基功能化离子液体(2a~2c3a~3c)。以2-溴-6-甲氧基萘与烯丙醇反应为模板反应,23为反应介质,考察反应的转化率和区域选择性。结果表明: 3为反应介质时,转化率和区域选择性均高于2。以溴代芳烃和烯丙醇为原料,3c为反应介质,醋酸钯催化Heck反应制得2-取代芳烃烯丙醇化合物,收率85%~89%,立体选择性均大于99%。所得产物的结构均经1H NMR, 13C NMR, IR, EI-MS和元素分析表征。

关 键 词:Heck反应  酰胺基功能化离子液体  烯丙醇化合物  合成  应用  
收稿时间:2014-10-30

Synthesis of New Multifunctionalized Ionic Liquids and Their Application in Heck Reaction of Synthesizing Allyl Alcohols
SUN Li,TAO Rong-shao,HU Wei-ya,PEI Wen.Synthesis of New Multifunctionalized Ionic Liquids and Their Application in Heck Reaction of Synthesizing Allyl Alcohols[J].Chinese Journal of Synthetic Chemistry,2015,23(10):899-903.
Authors:SUN Li  TAO Rong-shao  HU Wei-ya  PEI Wen
Institution:College of Chemical Engineering and Materials, Zhejiang University of Technology, Hangzhou 310014, China
Abstract:Six new amide-multifunctionalized ionic liquids(2a~2c3a~3c) were obtained by ion exchange of KPF-6 with 1-methyimidazole(or imidazole) and N-aryl-3-chlorobutanamide. The conversion and regioselectivities were investigated by the Heck reaction of 2-bromo-6-methoxynaphthylene with allyl alcohol using 2 or 3 as the medium. The results showed that the conversion and regioselectivities in 3 was better than in 2. Substituted aryl allyl alcohols were synthesized with high yields(85%~89%) and regioselectivities(>99%) by Heck reaction of haloaryl compounds with allyl alcohol, using 3c as the medium and palladium acetate as the catalyst. The structures were characterized by 1H NMR, 13C NMR, IR, EI-MS and elemental analysis.
Keywords:Heck reaction  amide-multifunctionalized ionic liquid  allyl alcohol compound  synthesis  application  
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