功能化离子液体的合成及在金属催化中的应用
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摘要
本论文合成了一系列功能化离子液体,包括腈基功能化离子液体,醚基功能化离子液体,羟基功能化离子液体,并考察了其作为绿色溶剂在金属催化的Suzuki, Heck, Stille和加氢反应中对反应催化效果的影响并研究了反应机理。
由腈基功能化离子液体为溶剂,咪唑基离子聚合物(IP)为保护剂和被两者稳定的钯纳米粒子构筑了代替传统的以乙腈为溶剂的催化体系。透射电子显微镜(TEM)研究表明,体系中钯纳米粒子是大小为5.0±0.2 nm,分布均匀的椭圆形颗粒。在Suzuki, Heck, Stille反应中,该体系在低负载量的情况下实现了高的催化活性和循环性。通过与核生长方法制备的大尺寸钯纳米粒子催化性能对比研究和紫外可见光谱(UV-Vis)表征,阐述了腈基离子液体中纳米催化的偶联反应机理。其催化行为遵循传统的有机溶剂中的金属催化,但在氧化加成后经历催化剂溶解,然后是转移、还原消去、催化剂重生。由于功能化离子液体和聚合物的双重保护作用,该体系十分稳定,因此有望作为传统钯/碳催化剂的替代品使用在碳-碳偶联反应中。
论文也考察了咪唑基和吡啶基两类醚基功能化离子液体在Suzuki反应中的应用。总的来说,侧链氧可以提供一个合适的配位环境,提高催化剂的稳定性,因此它是一个合适的Suzuki反应溶剂。但是,咪唑基离子液体侧链烷基取代基上氧的位置强烈地影响反应结果,而吡啶基离子液体并非如此。通过对咪唑基卡宾衍生物合成、分离,结合单晶衍射(X-ray)和氢核磁(1H NMR)的研究,发现侧链上氧位置不同所引起的其稳定性差异可能是导致在相应离子液体中不同反应结果的原因。
论文还研究了羟基功能化离子液体作为溶剂在Suzuki反应中的效果。分子尺度上的核磁研究表明,官能基团羟基可以与氯离子形成氢键,是其对氯离子高溶剂化能的主要原因。在Suzuki反应中,高的溶剂化能可以从帮助催化剂活性中心产生、促进底物氧化加成、加速卤素亲核转移、抑制催化剂中毒四方面加速催化循环和提高产率。
羟基功能化离子液体也同样作为溶剂在聚乙烯吡咯烷酮(PVP)保护的铑纳米粒子催化的加氢反应中被考察。PVP在羟基功能化离子液体中的溶解度是传统离子液体的10倍以上,提高的PVP含量使得纳米粒子被更好地稳定在离子液体中,达到更高的催化活性。在加氢反应中咪唑基阳离子和四氟硼酸阴离子提供了一个最佳的组合,是多种双键和三键化合物加氢的高效溶剂,并在苯乙烯加氢反应中实现了多达9次的循环使用。红外(IR)光谱研究显示,在多次的循环实验中聚苯乙烯生成,这可能是导致在后几次循环中催化剂活性稍有下降的主要原因。
A series of functionalized ionic liquids (IL), including nitrile, ether, and hydroxyl-functionalized, have been synthesized and were evaluated as solvents in Suzuki, Heck, Stille and hydrogenation reactions.
Highly stable palladium nanoparticles (Pd NPs), protected by an imidazolium-based ionic polymer (IP) in a functionalized IL, have been prepared. Transmission electron microscopy (TEM) analysis reveals that the Pd NPs have elliptical shape with average size of 5.0±0.2 nm. These Pd NPs are excellent pre-catalysts for Suzuki, Heck and Stille coupling reactions. For comparison, coupling reactions were catalyzed by lager Pd NPs synthesized by seeding growth method. On the basis of evidences by UV-Vis the mechanism catalyzed Pd NPs in ILs was proposed which follows classic catalytic cycle, involved oxidative addition, chemical etching, transmetalation, reductive elimination. The system may therefore be considered as an alternative to the traditional palladium on carbon (Pd/C) pre-catalyst employed in many C-C coupling reactions, also allowing reactions to be conducted under‘solvent-free’conditions.
Imidazolium- and pyridinium-based ILs with ether/polyether substituents have been evaluated as solvents for palladium catalyzed Suzuki C-C coupling reactions. In general, reactions proceed more efficiently in these solvents compared to other ILs, which is believed to be due to better stabilization of the palladium catalyst, involving weak interactions with the ether groups. Both position and the number of the oxygen atoms in the ether side-chain strongly influence the outcome of the coupling reactions in the imidazolium-based ILs, whereas for the pyridinium-based liquids no influence is observed. Carbene derivatives, generated from the imidazolium-based ILs, are synthesized, isolated, characterized by X-ray single crystal diffraction from stoichiometric reactions and believed to play a role by terminating the catalytic cycle.
A highly efficient system for the Suzuki reaction based on hydroxyl- functionalized ILs has been established. 1H NMR analysis reveals that hydroxyl group has strong interaction with Br- and Cl- which leads to higher solvation of halide than in unfunctionalized ILs. The role of the OH group appears to be multifactoral, with facilitating oxidative addition and generation of the catalytic active Pd(0), enhancing the metathesis step between base and halide, preventing catalyst poisoning by solvation, decreasing its nucleophilicity.
PVP stabilized rhodium nanoparticles are highly soluble in hydroxyl-functionalized ILs, providing an effective and highly stable catalytic system. Solubility of PVP is enhanced more than ten times by hydroxyl-functionalized ILs therefore provides an ability of Rh NPs to catalyze more efficiently in hydrogenation of unsaturated double and triple bonds. The combination of imidazolium-based cation and tetrafluoroborate is found to be the most efficient one in hydrogenation reactions. This system can be recycled more than nine times without significantly decreasing of catalytic activity in hydrogenation of styrene. However the slight drop of yields from seven batches is not due to catalyst leaching or decomposition which appears to be due to the formation of polystyrene identified by IR spectroscopy.
由腈基功能化离子液体为溶剂,咪唑基离子聚合物(IP)为保护剂和被两者稳定的钯纳米粒子构筑了代替传统的以乙腈为溶剂的催化体系。透射电子显微镜(TEM)研究表明,体系中钯纳米粒子是大小为5.0±0.2 nm,分布均匀的椭圆形颗粒。在Suzuki, Heck, Stille反应中,该体系在低负载量的情况下实现了高的催化活性和循环性。通过与核生长方法制备的大尺寸钯纳米粒子催化性能对比研究和紫外可见光谱(UV-Vis)表征,阐述了腈基离子液体中纳米催化的偶联反应机理。其催化行为遵循传统的有机溶剂中的金属催化,但在氧化加成后经历催化剂溶解,然后是转移、还原消去、催化剂重生。由于功能化离子液体和聚合物的双重保护作用,该体系十分稳定,因此有望作为传统钯/碳催化剂的替代品使用在碳-碳偶联反应中。
论文也考察了咪唑基和吡啶基两类醚基功能化离子液体在Suzuki反应中的应用。总的来说,侧链氧可以提供一个合适的配位环境,提高催化剂的稳定性,因此它是一个合适的Suzuki反应溶剂。但是,咪唑基离子液体侧链烷基取代基上氧的位置强烈地影响反应结果,而吡啶基离子液体并非如此。通过对咪唑基卡宾衍生物合成、分离,结合单晶衍射(X-ray)和氢核磁(1H NMR)的研究,发现侧链上氧位置不同所引起的其稳定性差异可能是导致在相应离子液体中不同反应结果的原因。
论文还研究了羟基功能化离子液体作为溶剂在Suzuki反应中的效果。分子尺度上的核磁研究表明,官能基团羟基可以与氯离子形成氢键,是其对氯离子高溶剂化能的主要原因。在Suzuki反应中,高的溶剂化能可以从帮助催化剂活性中心产生、促进底物氧化加成、加速卤素亲核转移、抑制催化剂中毒四方面加速催化循环和提高产率。
羟基功能化离子液体也同样作为溶剂在聚乙烯吡咯烷酮(PVP)保护的铑纳米粒子催化的加氢反应中被考察。PVP在羟基功能化离子液体中的溶解度是传统离子液体的10倍以上,提高的PVP含量使得纳米粒子被更好地稳定在离子液体中,达到更高的催化活性。在加氢反应中咪唑基阳离子和四氟硼酸阴离子提供了一个最佳的组合,是多种双键和三键化合物加氢的高效溶剂,并在苯乙烯加氢反应中实现了多达9次的循环使用。红外(IR)光谱研究显示,在多次的循环实验中聚苯乙烯生成,这可能是导致在后几次循环中催化剂活性稍有下降的主要原因。
A series of functionalized ionic liquids (IL), including nitrile, ether, and hydroxyl-functionalized, have been synthesized and were evaluated as solvents in Suzuki, Heck, Stille and hydrogenation reactions.
Highly stable palladium nanoparticles (Pd NPs), protected by an imidazolium-based ionic polymer (IP) in a functionalized IL, have been prepared. Transmission electron microscopy (TEM) analysis reveals that the Pd NPs have elliptical shape with average size of 5.0±0.2 nm. These Pd NPs are excellent pre-catalysts for Suzuki, Heck and Stille coupling reactions. For comparison, coupling reactions were catalyzed by lager Pd NPs synthesized by seeding growth method. On the basis of evidences by UV-Vis the mechanism catalyzed Pd NPs in ILs was proposed which follows classic catalytic cycle, involved oxidative addition, chemical etching, transmetalation, reductive elimination. The system may therefore be considered as an alternative to the traditional palladium on carbon (Pd/C) pre-catalyst employed in many C-C coupling reactions, also allowing reactions to be conducted under‘solvent-free’conditions.
Imidazolium- and pyridinium-based ILs with ether/polyether substituents have been evaluated as solvents for palladium catalyzed Suzuki C-C coupling reactions. In general, reactions proceed more efficiently in these solvents compared to other ILs, which is believed to be due to better stabilization of the palladium catalyst, involving weak interactions with the ether groups. Both position and the number of the oxygen atoms in the ether side-chain strongly influence the outcome of the coupling reactions in the imidazolium-based ILs, whereas for the pyridinium-based liquids no influence is observed. Carbene derivatives, generated from the imidazolium-based ILs, are synthesized, isolated, characterized by X-ray single crystal diffraction from stoichiometric reactions and believed to play a role by terminating the catalytic cycle.
A highly efficient system for the Suzuki reaction based on hydroxyl- functionalized ILs has been established. 1H NMR analysis reveals that hydroxyl group has strong interaction with Br- and Cl- which leads to higher solvation of halide than in unfunctionalized ILs. The role of the OH group appears to be multifactoral, with facilitating oxidative addition and generation of the catalytic active Pd(0), enhancing the metathesis step between base and halide, preventing catalyst poisoning by solvation, decreasing its nucleophilicity.
PVP stabilized rhodium nanoparticles are highly soluble in hydroxyl-functionalized ILs, providing an effective and highly stable catalytic system. Solubility of PVP is enhanced more than ten times by hydroxyl-functionalized ILs therefore provides an ability of Rh NPs to catalyze more efficiently in hydrogenation of unsaturated double and triple bonds. The combination of imidazolium-based cation and tetrafluoroborate is found to be the most efficient one in hydrogenation reactions. This system can be recycled more than nine times without significantly decreasing of catalytic activity in hydrogenation of styrene. However the slight drop of yields from seven batches is not due to catalyst leaching or decomposition which appears to be due to the formation of polystyrene identified by IR spectroscopy.
引文
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