基于Behera胺含超支化长氟链催化剂的设计、合成及其在绿色催化反应中之应用
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摘要
现代有机合成正在向高选择性、高产率、原子经济性、反应条件温和的方向发展,这就使得发展多功能高活性催化剂变得尤为重要。在该类催化体系中,多种不同的催化活性位点协同催化有机合成反应。
近几年来,许多新型高效的催化剂被研究开发,并将其用于催化有机合成反应,显示出良好的催化活性,如树状大分子催化剂和稀土金属催化剂。然而,树状大分子合成难度大,稀土催化剂也存在易潮解之不足。为了改善上述催化剂的催化活性,结合了树状催化剂活性位点多的优点,依据表面活性剂辅助稀土催化剂促进反应的原理,同时考虑到季铵盐表面活性剂可作为胶束催化剂,本论文设计、合成了一种新型含全氟烷基季铵盐的多支状羧酸稀土配合物催化体系。在该催化体系中,稳定的、拒水的全氟烷基链能够稳定稀土正离子,使催化剂存放稳定；树枝形大分子中有多个羧基,和稀土离子络合作为催化中心镶嵌在大分子的外围,催化活性点多,催化活性强；全氟烷基季铵盐可作为表面活性剂分散增溶底物又可以在水相中形成微乳液。
本论文以Behera胺作为多支状结构的合成单元,溴乙酰溴作为连接基,通过亲核取代反应引入长氟链,经过季铵化和甲酸水解反应合成了含有全氟烷基季铵盐的多羧酸的多功能催化配体。同时,利用溴乙酰溴作为连接基,将Behera胺与乙二胺等不同类型的端基二胺或长碳链脂肪伯胺如十六烷基胺等反应,合成出具有树状结构的十二羧酸催化剂及具有含碳长链的六羧酸钠Lewis碱催化剂。另外,Behera胺与溴乙酰溴的酰化产物与二乙醇胺发生取代、羟基胺化及水解反应合成了含三羧基的水溶性二乙烯三胺含氮配体。在合成一系列目标分子过程中,以溴乙酰溴作为高活性的连接基,大幅度提高了多支状化合物的合成效率。
本论文测定了所合成的不同类型的具碳长链季铵盐的多羧酸催化剂在水中的临界胶束浓度(CMC),其中含全氟辛基双季铵基三羧酸催化剂的临界胶束浓度小于10-4mol/L,其水溶液表面张力可以降至30 dyn·cm-1。同时,通过比较含不同类型碳链的催化剂在空气中吸水量的不同,证明了含全氟辛基链的配体具有良好的拒水性能。
将含全氟辛基季铵盐多羧酸催化剂用于水相协同稀土催化三组份合成2-氨基苯并吡喃衍生物的反应和Hantzsch反应,产率较高,且催化剂通过水相回收并可重复使用3次以上。同时,利用含三羧基的二乙烯三胺配体在碱性条件下与PdCl2络合后,可以实现水相催化Suzuki偶联反应,产率高达90%,且催化剂易回收可重复使用。另外,所合成的多支长碳链脂肪胺的六羧酸钠作为具表面活性的Lewis碱,可在水相催化Henry反应,产率高达96%,催化剂亦可回收重复使用3次以上。通过将多支状的十二酸催化剂辅助催化双氧水对苄醇衍生物的氧化反应,避免了使用传统的重金属离子催化剂,产物产率可达到80%。
本论文同时还研究了其它类型的绿色催化方法学：合成了离子型固体双磺酸催化剂。该催化体系可以在异相条件下催化吲哚对硝基苯乙烯的加成反应,并可得到中等产率的加成产物。该固体催化剂只需过滤,烘干,即可实现催化剂回收和重复使用。研究了水相中无催化剂条件下的醛和1,3-二羰基化合物的Knoevenagel缩合和Michael加成串联反应以及在无溶剂条件下无水三氯化铁催化的苄醇衍生物的胺化反应均能得到良好产率的目标产物,反应条件绿色环保,符合绿色化学的要求。
High selectivity, high yield, atom economy, and the mild reaction conditions are new trends of the catalytic reaction, which make the development of multi-functional catalyst with high activity become very important. In the multi-functional catalytic system, multiple parts of a catalyst or multiple catalysts work together to promote a specific reaction.
In recent years, many new and efficient catalysts have been developed and used to catalyze organic reactions, showing a good catalytic activity, which include the dendrimer catalysts and rare earth Lewis acid catalysts. However, dendrimer catalysts are not easily synthesized and rare earth Lewis acid catalysts are easily deliquescence. Based on the concept of surfactant-assisted rare earth catalytic system, combined with the merits of dendrimer catalyst and micelle catalyst of quaternary ammonium surfactant, a new quaternary ammonium salt containing perfluoroalkyl branch-like carboxylic acid and its rare-earth complex was designed and synthesized successflully. The stable and water repellent perfluoroalkyl chain stabilized the rare earth cation, prevent it from deliquescence; The complex of rare earth metals and carboxylic acid embedded in the periphery of the dendritic structure with high catalytic activity. As surfactant, perfluoroalkyl quaternary ammonium salt can form emulsion in the aqueous phase and make substrates disperse very well.
Using Behera's amine as dendron, bromoacetyl bromide as a linker, perfluoroalkyl chain was introduced by nucleophilic substitution. Then, after quaternization and hydrolysis reaction, the multibranched carboxylic acid catalyst containing perfluoroalkyl quaternary ammonium salt was synthesized. By acylation with bromoacetyl bromide, Behera's amine was transferred to a useful intermediate, which has been used to react with various primary amines to afford dendritic catalyst containing 12 carboxyl groups or the surfactant Lewis base containing 6 carboxylate groups. This intermediate was also used to react with diethanolamine, then after amination reaction of the hydroxyl group, the product was hydrolyzed to afford the water soluble diethylenetriamine (DETA) ligand. In the process of preparation of the target molecule, it was found that bromoacetyl bromide was a highly activity and high efficient for the synthesis of dendritic molecules based on Behera's amine, which may become one of the efficient method to the synthesis of dendrimers.
The CMC value was determined by testing surface tension of the surfactant catalyst with different carbon chains. Among all of them, the one containing single perfluorooctyl chain and two quaternary ammonium salt has the lowest CMC value of 10-4mol·L-1 with the surface tension of water reduced to 30 dyn.cm-1. At the same time, by comparing the results of water absorption properties of the catalyst in air, it was proved that the catalyst with perfluorooctyl chain has the best water resistant properties.
The multibranched carboxylic acid catalyst with perfluoroalkyl quaternary ammonium salt was used to coordinate with rare earth Lewis acid and catalyzed the three components reaction of aldehyde, malononitrile and naphthol to afford 2-amino benzopyran derivatives with good results. Meanwhile, it could also be very effective in the catalysis of Hantzsch reaction. The catalyst could be recycled and reused for more than 3 times. Additionally, the water soluble DETA ligand could coordinate with PdCl2 and has been applied in Suzuki reactions in water, with the yield up to 90%. The catalyst was recovered and reused for three cycles. The surfactant Lewis base containing 6 sodium carboxylate groups was used to catalyze Henry reaction in water with the yield up to 96%, and the catalyst could easily be recycled and reused for more than 3 times. By the assistant of dendritic catalyst containing 12 carboxyl groups, benzyl alcohol derivatives could be oxidized by H2O2 with the yield up to 80%, avoiding the use of traditional heavy metal catalysts.
In addition, this dissertation also includes the study of other types of green catalysis methodology. Ionic solid sulfonic acid was synthesized and used as heterogeneous catalyst to catalyze the addition reaction of indole and nitrobenzene to afford the products with moderate yields. By filtration and drying, the catalyst could be recovery and reused again. Finally, the cascade Knoevenagel condensation and Michael addition reaction of aldehydes and 1, 3-diketones in water and under catalyst free condition were explored, and the product can be purified just by filtration, washing and drying. The solvent-free amination of secondary benzylic alcohols with N-nucleophiles catalyzed by FeCl3 was also studied affording the products in good yields.
近几年来,许多新型高效的催化剂被研究开发,并将其用于催化有机合成反应,显示出良好的催化活性,如树状大分子催化剂和稀土金属催化剂。然而,树状大分子合成难度大,稀土催化剂也存在易潮解之不足。为了改善上述催化剂的催化活性,结合了树状催化剂活性位点多的优点,依据表面活性剂辅助稀土催化剂促进反应的原理,同时考虑到季铵盐表面活性剂可作为胶束催化剂,本论文设计、合成了一种新型含全氟烷基季铵盐的多支状羧酸稀土配合物催化体系。在该催化体系中,稳定的、拒水的全氟烷基链能够稳定稀土正离子,使催化剂存放稳定；树枝形大分子中有多个羧基,和稀土离子络合作为催化中心镶嵌在大分子的外围,催化活性点多,催化活性强；全氟烷基季铵盐可作为表面活性剂分散增溶底物又可以在水相中形成微乳液。
本论文以Behera胺作为多支状结构的合成单元,溴乙酰溴作为连接基,通过亲核取代反应引入长氟链,经过季铵化和甲酸水解反应合成了含有全氟烷基季铵盐的多羧酸的多功能催化配体。同时,利用溴乙酰溴作为连接基,将Behera胺与乙二胺等不同类型的端基二胺或长碳链脂肪伯胺如十六烷基胺等反应,合成出具有树状结构的十二羧酸催化剂及具有含碳长链的六羧酸钠Lewis碱催化剂。另外,Behera胺与溴乙酰溴的酰化产物与二乙醇胺发生取代、羟基胺化及水解反应合成了含三羧基的水溶性二乙烯三胺含氮配体。在合成一系列目标分子过程中,以溴乙酰溴作为高活性的连接基,大幅度提高了多支状化合物的合成效率。
本论文测定了所合成的不同类型的具碳长链季铵盐的多羧酸催化剂在水中的临界胶束浓度(CMC),其中含全氟辛基双季铵基三羧酸催化剂的临界胶束浓度小于10-4mol/L,其水溶液表面张力可以降至30 dyn·cm-1。同时,通过比较含不同类型碳链的催化剂在空气中吸水量的不同,证明了含全氟辛基链的配体具有良好的拒水性能。
将含全氟辛基季铵盐多羧酸催化剂用于水相协同稀土催化三组份合成2-氨基苯并吡喃衍生物的反应和Hantzsch反应,产率较高,且催化剂通过水相回收并可重复使用3次以上。同时,利用含三羧基的二乙烯三胺配体在碱性条件下与PdCl2络合后,可以实现水相催化Suzuki偶联反应,产率高达90%,且催化剂易回收可重复使用。另外,所合成的多支长碳链脂肪胺的六羧酸钠作为具表面活性的Lewis碱,可在水相催化Henry反应,产率高达96%,催化剂亦可回收重复使用3次以上。通过将多支状的十二酸催化剂辅助催化双氧水对苄醇衍生物的氧化反应,避免了使用传统的重金属离子催化剂,产物产率可达到80%。
本论文同时还研究了其它类型的绿色催化方法学：合成了离子型固体双磺酸催化剂。该催化体系可以在异相条件下催化吲哚对硝基苯乙烯的加成反应,并可得到中等产率的加成产物。该固体催化剂只需过滤,烘干,即可实现催化剂回收和重复使用。研究了水相中无催化剂条件下的醛和1,3-二羰基化合物的Knoevenagel缩合和Michael加成串联反应以及在无溶剂条件下无水三氯化铁催化的苄醇衍生物的胺化反应均能得到良好产率的目标产物,反应条件绿色环保,符合绿色化学的要求。
High selectivity, high yield, atom economy, and the mild reaction conditions are new trends of the catalytic reaction, which make the development of multi-functional catalyst with high activity become very important. In the multi-functional catalytic system, multiple parts of a catalyst or multiple catalysts work together to promote a specific reaction.
In recent years, many new and efficient catalysts have been developed and used to catalyze organic reactions, showing a good catalytic activity, which include the dendrimer catalysts and rare earth Lewis acid catalysts. However, dendrimer catalysts are not easily synthesized and rare earth Lewis acid catalysts are easily deliquescence. Based on the concept of surfactant-assisted rare earth catalytic system, combined with the merits of dendrimer catalyst and micelle catalyst of quaternary ammonium surfactant, a new quaternary ammonium salt containing perfluoroalkyl branch-like carboxylic acid and its rare-earth complex was designed and synthesized successflully. The stable and water repellent perfluoroalkyl chain stabilized the rare earth cation, prevent it from deliquescence; The complex of rare earth metals and carboxylic acid embedded in the periphery of the dendritic structure with high catalytic activity. As surfactant, perfluoroalkyl quaternary ammonium salt can form emulsion in the aqueous phase and make substrates disperse very well.
Using Behera's amine as dendron, bromoacetyl bromide as a linker, perfluoroalkyl chain was introduced by nucleophilic substitution. Then, after quaternization and hydrolysis reaction, the multibranched carboxylic acid catalyst containing perfluoroalkyl quaternary ammonium salt was synthesized. By acylation with bromoacetyl bromide, Behera's amine was transferred to a useful intermediate, which has been used to react with various primary amines to afford dendritic catalyst containing 12 carboxyl groups or the surfactant Lewis base containing 6 carboxylate groups. This intermediate was also used to react with diethanolamine, then after amination reaction of the hydroxyl group, the product was hydrolyzed to afford the water soluble diethylenetriamine (DETA) ligand. In the process of preparation of the target molecule, it was found that bromoacetyl bromide was a highly activity and high efficient for the synthesis of dendritic molecules based on Behera's amine, which may become one of the efficient method to the synthesis of dendrimers.
The CMC value was determined by testing surface tension of the surfactant catalyst with different carbon chains. Among all of them, the one containing single perfluorooctyl chain and two quaternary ammonium salt has the lowest CMC value of 10-4mol·L-1 with the surface tension of water reduced to 30 dyn.cm-1. At the same time, by comparing the results of water absorption properties of the catalyst in air, it was proved that the catalyst with perfluorooctyl chain has the best water resistant properties.
The multibranched carboxylic acid catalyst with perfluoroalkyl quaternary ammonium salt was used to coordinate with rare earth Lewis acid and catalyzed the three components reaction of aldehyde, malononitrile and naphthol to afford 2-amino benzopyran derivatives with good results. Meanwhile, it could also be very effective in the catalysis of Hantzsch reaction. The catalyst could be recycled and reused for more than 3 times. Additionally, the water soluble DETA ligand could coordinate with PdCl2 and has been applied in Suzuki reactions in water, with the yield up to 90%. The catalyst was recovered and reused for three cycles. The surfactant Lewis base containing 6 sodium carboxylate groups was used to catalyze Henry reaction in water with the yield up to 96%, and the catalyst could easily be recycled and reused for more than 3 times. By the assistant of dendritic catalyst containing 12 carboxyl groups, benzyl alcohol derivatives could be oxidized by H2O2 with the yield up to 80%, avoiding the use of traditional heavy metal catalysts.
In addition, this dissertation also includes the study of other types of green catalysis methodology. Ionic solid sulfonic acid was synthesized and used as heterogeneous catalyst to catalyze the addition reaction of indole and nitrobenzene to afford the products with moderate yields. By filtration and drying, the catalyst could be recovery and reused again. Finally, the cascade Knoevenagel condensation and Michael addition reaction of aldehydes and 1, 3-diketones in water and under catalyst free condition were explored, and the product can be purified just by filtration, washing and drying. The solvent-free amination of secondary benzylic alcohols with N-nucleophiles catalyzed by FeCl3 was also studied affording the products in good yields.
引文
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