过渡金属催化的环化反应及其在固载化不对称合成中的应用
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摘要
过渡金属催化的环化反应是构筑各类环骨架尤其是多环骨架化合物非常有效的合成方法之一,也是有机合成中的一个重要研究领域,在近几十年里得到了很大的发展。由于过渡金属催化的环化反应条件较为温和,适用范围广,产物易分离,对底物的兼容性较好,选择性好,产率较高,已经被广泛地应用于有机化学的许多研究领域,特别是被成功的应用于许多具有生物活性的杂环类化合物的合成中。例如天然产物、药物分子和生物活性化合物的合成,聚合物、液晶、超分子、以及配体的合成等。其将来的发展一方面是发现更多快速、有效、高可靠、高选择性的反应,另一方面是以更精确、更富有创造性的方法来发掘其潜力。我们相信,在不久的将来过渡金属催化必将成为化学研究的一个重要的、不可缺少的有效手段,迎来更美好的明天。
本论文重点研究了由金属Pd,Cu催化的多组分串联反应,及其在固载化不对称合成中的应用。论文主要分为四部分:
首先,就过渡金属催化的环化反应做一综述性的介绍,概括了近些年来利用Pd,Cu在氧化反应、碳-碳键的构建、亲核试剂对碳-碳多键的加成反应以及烯炔等不饱和化合物合环反应中的应用,为设计过渡金属催化的新反应提供了新的思路。
其次,我们研究了在绿色化学条件下,利用Cu(Ⅰ)参与的click多组分反应。近年来,RTILs作为一种“绿色溶剂”在催化和有机反应中发挥了独特的作用,受到了广泛的关注。我们正是利用其特殊的优点,成功的发展了一种新型、高效的绿色合成方法:室温下,在离子液体/H_2O的混合溶剂中,用一锅法高产率的得到一系列结构新颖的具有潜在药理活性的氮杂环化合物——1,4-二取代-1,2,3-三唑,此方法高效、简洁、环保,而且底物适应性强,不管是对于芳基碘代物还是sp3-杂化的烷基卤代物都可以以很高的产率得到产物,催化剂廉价易得、催化体系对于空气十分稳定,而且催化体系可做到在5次循环使用后,没有明显的活性损失;极大的丰富了绿色化学条件下的有机合成和多组分反应研究,能够用做模板反应去高效率的合成复杂的药物分子,为该类化合物的合成和性质研究提供了可靠的方法和可筛选的化合物。
再次,我们将“click”化学引入到了固载化有机催化剂催化的不对称领域,拓展了其用途。近些年来,应用脯氨酸及其衍生物为代表的有机催化剂进行不对称催化,成为有机化学最热门的研究方向。我们以便宜的脯氨酸作为手性源,官能化的丙胺基硅胶作为起始原料,通过Cu(Ⅰ)催化的炔-叠氮反应的“click”化学反应步骤,合成了用N锚定的硅胶固载化的四氢吡咯-三唑的手性催化剂,并将它们应用到了Michael加成反应中,高效的催化Michael加成反应的进行,得到非常好的非对映选择性和ee值,在一些底物参与的反应中,得到了非均相催化难以达到的结果;由于Cu(Ⅰ)催化的炔-叠氮反应的“click”化学,本身具有宽广的底物范围和温和的反应条件,为合成多样的固载化三唑手性催化剂提供了模块化和可调特征的模板反应;并且此催化剂在多次使用后仍可保持其高效的催化效果,体现了固载化催化剂方便回收和反复循环使用的特点,发展了固相载体作为异相反应的应用潜力。
最后,我们通过Pd催化的反应,发展了一个可以快速高效合成多取代的芴酮、芴醇、菲等稠环酚类及其衍生物的多组分串联环化反应,有效的合成了有潜在生物活性的一系列芴类化合物。反应过程显示了以下优点:1)反应过程简单,产率高、区域选择性好;2)在一锅反应中同时构建多个C-C键,提高了原子经济性;3)反应原料廉价易得、条件温和可以用于各种多取代芴、稠环酚类及其衍生物的制备。
Transition metal facilitated reactions have a long history in organometallic chemistry and new reactions continue to be discovered and developed.In recent years, the synthesis of organic heterocyclic and polycyclic molecules has especially benefited from novel Pd,Cu facilitated cyclization of heteroatoms to alkenes,alkynes and arenes.Transition-metal catalysis provides the opportunity to generate complex molecular frameworks from simple,readily available substrates in an efficient,easy and selective manner.It has been widely used in organic research area,eapecially for some biologic,pharmaceutical and materials interest heterocycles.The relatively low cost,low temperature and the realization of catalysis in many instances makes it an attractive reagent.Reasonablely,we can believe that transition metal will have a bright future.
This thesis aims at the studies on the Pd,Cu-catalyzed multi-component cyclization reactions and solid-supported organocatalyst for the enantioselective Michael addition. It mainly consists of the following four parts:
In chapter 1,a comprehensive overview in the field of Pd,Cu catalyzed cyclization is summarized.Copper and palladium salts can act as catalytic cross-coupling agents, Lewis acids and oxidizing agents and be used in oxidation reaction,C-C bond formation,the addition of nucleophiles to C-C multiple bonds to form some new organic heterocyclic and polycyclic molecules.
In chapter 2,we introduced the concept of“click”chemistry and copper-(Ⅰ)-catalyzed 1,2,3-triazole multi-component reactions under green chemistry. Room temperature ionic liquids are environmentally benign solvents due to their unique chemical and physical properties,and have proved to be especially useful in the case of catalytic reactions,Herein,we have demonstrated that the ionic liquid/H_2O was a good reaction medium for the one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles using either halides at sp3-hybridized carbon atoms or halides at sp2-hybridized carbon atoms in good yields.Better performance was obtained than that of conventional reaction condition.This procedure permits extensive recycling of the solvent without substantial loss in activity within five times.On the basis of the current efforts,it seems to be likely that a number of metal catalyzed transformations could be performed equally well or even more effectively in this ionic liquid.
In chapter 3,we extended the application of“click”chemistry to the field of solid-supported asymmetric Michael addition reaction.Recently,a significant amount of effort has been devoted towards the modification of the proline and it's derivatives, particularly chiral pyrrolidine-triazole,which are made through copper-mediated 1,3-dipolar cycloaddition between azides and alkynes(click chemistry),have been found to be very effective in asymmetric Michael addition reaction.These organocatalysts are generally considered environmentally benign because the use of metals is avoided,however,it would be even more desirable and economical to develop an immobilized,easily recoverable,and reusable catalyst to perform this reaction.
We prepared a new silica-supported organocatalyst and successfully applied to the asymmetric Michael addition reaction of ketones to nitroalkenes.The reactions proceeded smoothly at room temperature to give high yields(up to 98%),excellent diastereoselectivities(syn/anti ratio up to 20:1),and excellent enantioselectivities(ee up to 93%).Furthermore,this procedure permits extensive recycling of the catalyst without substantial loss of activity.
Therefore,Cu(Ⅰ)-catalyzed 1,3-dipolar“click”azide-alkyne cycloaddition provides the modular and tunable features for the solid-supported pyrrolidine-triazole catalysts. In addition,it is worthy of noting that the triazole moiety introduced cannot only act as a positive phase tag to complete the reaction in a broad range of solvents,but can also serve as an efficient chiral-induction group to ensure a high selectivity.On the basis of the current work,it seems likely that a number of asymmetric reactions could be performed equally well with this immobilized organocatalyst.
In chapter 4,we summarized the Catellani reaction and a number of extention via this reaction,introduced palladium catalyzed addition to carbonyl groups and arylation.Finally,a powerful new methodology for the rapid synthesis of highly substituted poly-aromatic ketones,tertiary alcohols,and phenols has been developed. Of particular significance is that this methodology not only provide a new method for the synthesis of poly-aromatic products,but also is a good incorporation of domino reaction into typical Catellani reaction.Through a lot of work on the addition of ketones,aldehydes and enolates,possibly mechanism has been discussed,synthetic utility of palladium intermediates and their ability to show different reactivity patterns has been demonstrated.
本论文重点研究了由金属Pd,Cu催化的多组分串联反应,及其在固载化不对称合成中的应用。论文主要分为四部分:
首先,就过渡金属催化的环化反应做一综述性的介绍,概括了近些年来利用Pd,Cu在氧化反应、碳-碳键的构建、亲核试剂对碳-碳多键的加成反应以及烯炔等不饱和化合物合环反应中的应用,为设计过渡金属催化的新反应提供了新的思路。
其次,我们研究了在绿色化学条件下,利用Cu(Ⅰ)参与的click多组分反应。近年来,RTILs作为一种“绿色溶剂”在催化和有机反应中发挥了独特的作用,受到了广泛的关注。我们正是利用其特殊的优点,成功的发展了一种新型、高效的绿色合成方法:室温下,在离子液体/H_2O的混合溶剂中,用一锅法高产率的得到一系列结构新颖的具有潜在药理活性的氮杂环化合物——1,4-二取代-1,2,3-三唑,此方法高效、简洁、环保,而且底物适应性强,不管是对于芳基碘代物还是sp3-杂化的烷基卤代物都可以以很高的产率得到产物,催化剂廉价易得、催化体系对于空气十分稳定,而且催化体系可做到在5次循环使用后,没有明显的活性损失;极大的丰富了绿色化学条件下的有机合成和多组分反应研究,能够用做模板反应去高效率的合成复杂的药物分子,为该类化合物的合成和性质研究提供了可靠的方法和可筛选的化合物。
再次,我们将“click”化学引入到了固载化有机催化剂催化的不对称领域,拓展了其用途。近些年来,应用脯氨酸及其衍生物为代表的有机催化剂进行不对称催化,成为有机化学最热门的研究方向。我们以便宜的脯氨酸作为手性源,官能化的丙胺基硅胶作为起始原料,通过Cu(Ⅰ)催化的炔-叠氮反应的“click”化学反应步骤,合成了用N锚定的硅胶固载化的四氢吡咯-三唑的手性催化剂,并将它们应用到了Michael加成反应中,高效的催化Michael加成反应的进行,得到非常好的非对映选择性和ee值,在一些底物参与的反应中,得到了非均相催化难以达到的结果;由于Cu(Ⅰ)催化的炔-叠氮反应的“click”化学,本身具有宽广的底物范围和温和的反应条件,为合成多样的固载化三唑手性催化剂提供了模块化和可调特征的模板反应;并且此催化剂在多次使用后仍可保持其高效的催化效果,体现了固载化催化剂方便回收和反复循环使用的特点,发展了固相载体作为异相反应的应用潜力。
最后,我们通过Pd催化的反应,发展了一个可以快速高效合成多取代的芴酮、芴醇、菲等稠环酚类及其衍生物的多组分串联环化反应,有效的合成了有潜在生物活性的一系列芴类化合物。反应过程显示了以下优点:1)反应过程简单,产率高、区域选择性好;2)在一锅反应中同时构建多个C-C键,提高了原子经济性;3)反应原料廉价易得、条件温和可以用于各种多取代芴、稠环酚类及其衍生物的制备。
Transition metal facilitated reactions have a long history in organometallic chemistry and new reactions continue to be discovered and developed.In recent years, the synthesis of organic heterocyclic and polycyclic molecules has especially benefited from novel Pd,Cu facilitated cyclization of heteroatoms to alkenes,alkynes and arenes.Transition-metal catalysis provides the opportunity to generate complex molecular frameworks from simple,readily available substrates in an efficient,easy and selective manner.It has been widely used in organic research area,eapecially for some biologic,pharmaceutical and materials interest heterocycles.The relatively low cost,low temperature and the realization of catalysis in many instances makes it an attractive reagent.Reasonablely,we can believe that transition metal will have a bright future.
This thesis aims at the studies on the Pd,Cu-catalyzed multi-component cyclization reactions and solid-supported organocatalyst for the enantioselective Michael addition. It mainly consists of the following four parts:
In chapter 1,a comprehensive overview in the field of Pd,Cu catalyzed cyclization is summarized.Copper and palladium salts can act as catalytic cross-coupling agents, Lewis acids and oxidizing agents and be used in oxidation reaction,C-C bond formation,the addition of nucleophiles to C-C multiple bonds to form some new organic heterocyclic and polycyclic molecules.
In chapter 2,we introduced the concept of“click”chemistry and copper-(Ⅰ)-catalyzed 1,2,3-triazole multi-component reactions under green chemistry. Room temperature ionic liquids are environmentally benign solvents due to their unique chemical and physical properties,and have proved to be especially useful in the case of catalytic reactions,Herein,we have demonstrated that the ionic liquid/H_2O was a good reaction medium for the one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles using either halides at sp3-hybridized carbon atoms or halides at sp2-hybridized carbon atoms in good yields.Better performance was obtained than that of conventional reaction condition.This procedure permits extensive recycling of the solvent without substantial loss in activity within five times.On the basis of the current efforts,it seems to be likely that a number of metal catalyzed transformations could be performed equally well or even more effectively in this ionic liquid.
In chapter 3,we extended the application of“click”chemistry to the field of solid-supported asymmetric Michael addition reaction.Recently,a significant amount of effort has been devoted towards the modification of the proline and it's derivatives, particularly chiral pyrrolidine-triazole,which are made through copper-mediated 1,3-dipolar cycloaddition between azides and alkynes(click chemistry),have been found to be very effective in asymmetric Michael addition reaction.These organocatalysts are generally considered environmentally benign because the use of metals is avoided,however,it would be even more desirable and economical to develop an immobilized,easily recoverable,and reusable catalyst to perform this reaction.
We prepared a new silica-supported organocatalyst and successfully applied to the asymmetric Michael addition reaction of ketones to nitroalkenes.The reactions proceeded smoothly at room temperature to give high yields(up to 98%),excellent diastereoselectivities(syn/anti ratio up to 20:1),and excellent enantioselectivities(ee up to 93%).Furthermore,this procedure permits extensive recycling of the catalyst without substantial loss of activity.
Therefore,Cu(Ⅰ)-catalyzed 1,3-dipolar“click”azide-alkyne cycloaddition provides the modular and tunable features for the solid-supported pyrrolidine-triazole catalysts. In addition,it is worthy of noting that the triazole moiety introduced cannot only act as a positive phase tag to complete the reaction in a broad range of solvents,but can also serve as an efficient chiral-induction group to ensure a high selectivity.On the basis of the current work,it seems likely that a number of asymmetric reactions could be performed equally well with this immobilized organocatalyst.
In chapter 4,we summarized the Catellani reaction and a number of extention via this reaction,introduced palladium catalyzed addition to carbonyl groups and arylation.Finally,a powerful new methodology for the rapid synthesis of highly substituted poly-aromatic ketones,tertiary alcohols,and phenols has been developed. Of particular significance is that this methodology not only provide a new method for the synthesis of poly-aromatic products,but also is a good incorporation of domino reaction into typical Catellani reaction.Through a lot of work on the addition of ketones,aldehydes and enolates,possibly mechanism has been discussed,synthetic utility of palladium intermediates and their ability to show different reactivity patterns has been demonstrated.
引文
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