离子液体中钯、钌催化的碳—杂键和碳—碳键形成反应研究
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摘要
室温离子液体(Room Temperature Ionic Liquids, RTILs)是一类特殊的液体熔融盐,具有优良的物理化学性质及可修饰、调变的阴阳离子结构,且可循环利用,被认为是替代常用挥发有机溶剂的新型绿色溶剂。近年来,离子液体作为一种绿色溶剂、催化剂以及催化剂的液相载体在有机反应中发挥了独特的作用,受到人们越来越多的关注。
碳-碳和碳-杂原子键的形成反应是有机合成研究的中心问题。利用离子液体作为有机反应的溶剂、催化剂及催化剂的液相载体完成碳-碳键和碳-杂键的形成反应已成为目前该领域研究的热点。本论文在综述了近年来以离子液体作为绿色溶剂、催化剂及催化剂的液相载体在碳-碳键和碳-杂键形成反应中的应用研究的基础上,进一步探索过渡金属催化的碳-碳键和碳-杂键形成反应在离子液体中进行的可能性,主要研究内容如下:
第一部分:按文献方法制备了疏水性离子液体1-丁基-3-甲基咪唑六氟磷酸盐离子液体([BMIm] PF6),研究了在该离子液体中Pd(PPh3)4催化PhSeSnBu3与卤代烃的交叉偶联反应,发现该反应在80 oC能顺利进行,以高产率合成了相应的芳基硒醚,为碳-硒键的形成提供了绿色新途径。研究了在[BMIm] PF6中三氯化钌催化醇、酚、硫醇和硫酚与乙酸酐的乙酰化反应,发现该反应在45 oC下能顺利进行,以高产率合成了各种乙酸酯类化合物,为各种醇、酚、硫醇的乙酰化反应提供了绿色新方法。在上述两类碳-杂键形成反应中,离子液体和催化剂可循环使用多次,对反应基本无影响。
第二部分:按文献方法制备了苯基锡烷和炔基锡烷,研究了它们在[BMIm] PF6中Pd(PPh3)4催化下与卤代芳烃的Stille偶联反应,发现该反应在80 oC能顺利进行,以良好的产率生成相应的偶联产物。研究了PdCl2(PPh3)2催化下芳基溴与端炔在[BMIm] PF6中的Sonogashira偶联反应,结果表明,该反应在60-80 oC下能顺利进行,以较好的产率合成了各种芳炔。在上述两类碳-碳键形成反应中,离子液体和催化剂也可循环使用多次。
Room temperature ionic liquids, as a new green reaction medium as well as catalyst, possess super-ordinary physical chemistry properties and easily modified the structure of anions and cations. Ionic liquids were considered as the replacement of the commonly used volatile organic solvent. Recently, ionic liquids as a kind of green solvent and catalyst even as a carrier for catalyst have received much attention due to the important roles they played in organic reactions.
Carbon-carbon and carbon-heteroatom bond-forming reactions are central to organic synthesis. Ionic liquids as a solvent, catalyst or carrier for catalyst in carbon-carbon and carbon-heteroatom bond-forming reactions have attracted great interest in organic synthesis. In this thesis, based on the reviewing developments of ionic liquids as a kind of green solvent, catalyst and carrier for catalyst in organic synthesis, we explored the possibility of transition-metal-catalyzed carbon-carbon and carbon-heteroatom bond-forming reactions in ionic liquids. The details are summarized as following:
Part one: According to the literature procedure, we prepared a hydrophobic ionic liquid, namely, 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIm] PF6). We investigated the cross-coupling reaction of phenyl tributylstannyl selenide (PhSeSnBu3) with aryl and alkyl halides in the presence of Pd(PPh3)4 in [BMIm] PF6. It was found that the reaction proceeded smoothly at 80 oC to afford the corresponding diaryl and alkylaryl selenides in moderate to good yields, providing a green procedure for the formation of carbon-selenium. Ruthenium (III) chloride catalyzed acylation reactions of alcohols, phenols, and thiols in [BMIm] PF6 were also investigated. It was found that the acylation reactions could proceed smoothly at 45 oC to afford a variety of acetate in high yields, providing a green and practical method for acylation of alcohols, phenols, and thiols. In the two reactions above, the catalytic system composed of ionic liquid and the catalysts can be recycled many times without noticeable loss of the catalyst activity.
Part two: According to the literature method, we prepared phenylstannane and alkynylstannanes and investigated Stille coupling reactions of organostannanes with aryl halides in [BMIm] PF6 in the presence of Pd(PPh3)4. It was found that the Stille reaction proceeded smoothly at 80 oC to give corresponding coupled products in good high yields. We also investigated the Sonogashira coupling reactions of aryl bromides with terminal alkynes in [BMIm] PF6. It was found that the Sonogashira coupling reaction proceeded smoothly at 60 ~ 80 oC in [BMIm] PF6, to afford a variety of aryl alkynes in high yields. In the two carbon-carbon bond-forming reactions, the [BMIm] PF6 and the catalysts could be recycled several times.
碳-碳和碳-杂原子键的形成反应是有机合成研究的中心问题。利用离子液体作为有机反应的溶剂、催化剂及催化剂的液相载体完成碳-碳键和碳-杂键的形成反应已成为目前该领域研究的热点。本论文在综述了近年来以离子液体作为绿色溶剂、催化剂及催化剂的液相载体在碳-碳键和碳-杂键形成反应中的应用研究的基础上,进一步探索过渡金属催化的碳-碳键和碳-杂键形成反应在离子液体中进行的可能性,主要研究内容如下:
第一部分:按文献方法制备了疏水性离子液体1-丁基-3-甲基咪唑六氟磷酸盐离子液体([BMIm] PF6),研究了在该离子液体中Pd(PPh3)4催化PhSeSnBu3与卤代烃的交叉偶联反应,发现该反应在80 oC能顺利进行,以高产率合成了相应的芳基硒醚,为碳-硒键的形成提供了绿色新途径。研究了在[BMIm] PF6中三氯化钌催化醇、酚、硫醇和硫酚与乙酸酐的乙酰化反应,发现该反应在45 oC下能顺利进行,以高产率合成了各种乙酸酯类化合物,为各种醇、酚、硫醇的乙酰化反应提供了绿色新方法。在上述两类碳-杂键形成反应中,离子液体和催化剂可循环使用多次,对反应基本无影响。
第二部分:按文献方法制备了苯基锡烷和炔基锡烷,研究了它们在[BMIm] PF6中Pd(PPh3)4催化下与卤代芳烃的Stille偶联反应,发现该反应在80 oC能顺利进行,以良好的产率生成相应的偶联产物。研究了PdCl2(PPh3)2催化下芳基溴与端炔在[BMIm] PF6中的Sonogashira偶联反应,结果表明,该反应在60-80 oC下能顺利进行,以较好的产率合成了各种芳炔。在上述两类碳-碳键形成反应中,离子液体和催化剂也可循环使用多次。
Room temperature ionic liquids, as a new green reaction medium as well as catalyst, possess super-ordinary physical chemistry properties and easily modified the structure of anions and cations. Ionic liquids were considered as the replacement of the commonly used volatile organic solvent. Recently, ionic liquids as a kind of green solvent and catalyst even as a carrier for catalyst have received much attention due to the important roles they played in organic reactions.
Carbon-carbon and carbon-heteroatom bond-forming reactions are central to organic synthesis. Ionic liquids as a solvent, catalyst or carrier for catalyst in carbon-carbon and carbon-heteroatom bond-forming reactions have attracted great interest in organic synthesis. In this thesis, based on the reviewing developments of ionic liquids as a kind of green solvent, catalyst and carrier for catalyst in organic synthesis, we explored the possibility of transition-metal-catalyzed carbon-carbon and carbon-heteroatom bond-forming reactions in ionic liquids. The details are summarized as following:
Part one: According to the literature procedure, we prepared a hydrophobic ionic liquid, namely, 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIm] PF6). We investigated the cross-coupling reaction of phenyl tributylstannyl selenide (PhSeSnBu3) with aryl and alkyl halides in the presence of Pd(PPh3)4 in [BMIm] PF6. It was found that the reaction proceeded smoothly at 80 oC to afford the corresponding diaryl and alkylaryl selenides in moderate to good yields, providing a green procedure for the formation of carbon-selenium. Ruthenium (III) chloride catalyzed acylation reactions of alcohols, phenols, and thiols in [BMIm] PF6 were also investigated. It was found that the acylation reactions could proceed smoothly at 45 oC to afford a variety of acetate in high yields, providing a green and practical method for acylation of alcohols, phenols, and thiols. In the two reactions above, the catalytic system composed of ionic liquid and the catalysts can be recycled many times without noticeable loss of the catalyst activity.
Part two: According to the literature method, we prepared phenylstannane and alkynylstannanes and investigated Stille coupling reactions of organostannanes with aryl halides in [BMIm] PF6 in the presence of Pd(PPh3)4. It was found that the Stille reaction proceeded smoothly at 80 oC to give corresponding coupled products in good high yields. We also investigated the Sonogashira coupling reactions of aryl bromides with terminal alkynes in [BMIm] PF6. It was found that the Sonogashira coupling reaction proceeded smoothly at 60 ~ 80 oC in [BMIm] PF6, to afford a variety of aryl alkynes in high yields. In the two carbon-carbon bond-forming reactions, the [BMIm] PF6 and the catalysts could be recycled several times.
引文
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