构筑手性多孔有机材料应用于多相不对称有机催化
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摘要
多孔有机材料由于具有大的比表面积、稳定性好、重量轻以及易于功能化等诸多优点,被广泛应用在气体存储分离、传感、有机光电和多相催化等领域。尤其是具有催化活性的多孔有机材料引起了人们的研究兴趣。目前,关于有机多孔材料在多相催化领域应用的研究工作主要有两类：一类是通过"bottom-up"策略将有机金属配合物嵌入有机多孔材料骨架来构建多相催化剂；一类是是将有机多孔材料作为载体,通过后修饰的方法负载金属纳米颗粒作为多相催化剂。迄今为止,还没有将有机孔材料应用于多相不对称有机催化的例子见诸报道。随着有机小分子催化的迅猛发展,将手性有机催化剂与多孔有机材料结合起来,通过" bottom-up "策略构筑纯有机骨架的手性有机多孔材料来实现多相不对称有机催化将会是该领域中一个新的、有挑战性的研究方向。
本论文的主要研究内容为基于有机小分子催化剂(J(?)rgensen-Hayashi catalyst, MacMillan catalyst)骨架的手性有机多孔材料的设计、合成、表征以及多相不对称有机催化应用。相应地,本论文的主要研究工作分为以下四个部分：
一.通过"bottom-up"策略成功将J(?)rgensen-Hayashi催化剂嵌入手性多孔有机材料骨架,合成了手性多孔有机材料JH-CPP,并实现了该材料在多相催化不对称Michael加成反应中的应用。该材料高的比表面积(881m2／g)、开放的和相互交叉贯通的孔道结构使得其在催化不对称Michael加成反应时有着和均相催化剂相媲美的催化效果,并且该材料可以循环使用四次,产物的ee值没有降低(97-99%ee)。
二.进一步拓展了JH-CPP材料在催化硝基甲烷对α,β-不饱和醛的不对称Michael加成反应中的应用。研究发现,JH-CPP材料在催化该反应时,除了有着和均相催化剂相媲美的催化效果外,它还优越于采用传统方式固载的J(?)rgensen-Hayashi催化剂,并且该材料可以循环使用六次,产物的ee值没有任何降低(95-96%ee)。
三.通过"bottom-up"策略成功将MacMillan催化剂嵌入手性多孔有机材料骨架,实现了该材料在多相催化不对称Diels-Alder反应中的应用。通过调节不同的结构性砌块合成了三种具有不同比表面积的材料(Mac-CPP-1, Mac-CPP-2, Mac-CPP-3),考察了材料的结构一性质一催化活性之间的关系。
四.通过“自负载”策略合成了MacMillan聚合物催化剂(Mac-ChiOSP),并研究了其在催化不对称Diels-Alder反应中的应用。研究发现该手性材料可以实现均相条件下催化反应,多相条件下回收循环。与“后合成”策略得到的固载催化剂相比,通过“自负载”策略合成的多聚MacMillan催化剂有着均一分布的和高密度的催化活性位,再加上这种均相条件下催化反应的特性,使得该材料有着和均相催化剂同等的催化活性和对映选择性。并且该材料可以循环使用三次,产物的ee值没有降低(86-90%ee for endo,84-88%ee for exo)。
Due to their inherent porosity, large specific surface area, light weight, and easy functionalization at the molecular level, porous organic polymers have recently received significant attention for potential applications in gas storage/separation, light-harvesting, sensoring, and heterogeneous catalysis. Especially, the construction of functional porous organic polymers via bottom-up strategy for heterogeneous catalysis has made tremendous development in recent years. The reported research works in this field are mainly focused on the embedding of the organometallics into the polymers, or the encapsulation of the metal particles into the porous organic polymers. Nevertheless, to date, the embedding of chiral organocatalysts into the frameworks of the porous organic polymers via bottom-up strategy has been not reported yet. In this context, with the rapid development of asymmetric organocatalysis, construction of organocatalysts embedded chiral porous organic polymers via bottom-up strategy for the heterogeneous asymmetric organocatalysis will be a promising and challenging research issue.
Accordingly, the main research contents of this thesis is to design, synthesize and characterize the chiral porous organic polymers based on chiral organocatalysts (J(?)rgensen-Hayashi catalyst and MacMillan catalyst), and utilize them in the heterogeneous asymmetric organocatalysis. The main achievements of this thesis could be divided into the following four parts:
1. The Jorgensen-Hayashi catalyst has been successfully embedded into a nanoporous polymer via the bottom-up strategy. The obtained JH-CPP polymer has been utilized as a highly efficient heterogeneous organocatalyst for the asymmetric Michael addition reaction. Owing to the high BET surface area (881m2/g), as well as the widely pervasive and interconnected pores, JH-CPP possesses comparable activity and enantioselectivity with the homogeneous JH catalyst. Furthermore, the JH-CPP catalyst can be reused for at least four times with no decrease of enantioselectivity (97-99%ee).
2. To further expanding the catalytic application of JH-CPP to other asymmetric reactions, we have also applied JH-CPP as the heterogeneous organocatalyst in the asymmetric Michael addition reaction of nitromethane with a, p-unsaturated aldehydes. The JH-CPP catalyst shows comparable catalytic efficiency with the homogeneous JH catalyst, and can be reused for at least six times with no decrease of enantioselectivity (95-96%ee). Notably, the catalytic efficiency of JH-CPP catalyst is superior to that of the traditional immobilized J(?)rgensen-Hayashi catalyst.
3. The MacMillan catalyst has been successfully embedded into nanoporous polymers via the bottom-up strategy, and the obtained polymers have been applied as highly efficient heterogeneous organocatalysts for the asymmetric Diels-Alder reaction. The specific surface areas of the three MacMillan catalyst-embedded chiral porous polymers (Mac-CPP-1, Mac-CPP-2, Mac-CPP-3) can be adjusted by changing the size of the structural building blocks. We have also investigated the structure-property-catalytic activity relationship of these MacMillan catalyst-embedded chiral porous polymers.
4. We have synthesized a "self-supported" polymeric MacMillan catalyst (Mac-ChiOSP), which can be applied as an efficient catalyst for homogeneous organocatalysis and heterogeneous recycling for the asymmetric Diels-Alder reaction. In comparison with thosee immobilized MacMillan catalysts, this "self-supported" polymeric MacMillan catalyst possesses homogeneously-distributed and highly-concentrated catalytic sites. This advantage together with the homogeneous catalytic nature ensured its excellent catalytic ability. Furthermore, the heterogeneous catalyst can be reused for at least three times with no decrease of enantioselectivity (86-90%ee for endo,84-88%for exo).
本论文的主要研究内容为基于有机小分子催化剂(J(?)rgensen-Hayashi catalyst, MacMillan catalyst)骨架的手性有机多孔材料的设计、合成、表征以及多相不对称有机催化应用。相应地,本论文的主要研究工作分为以下四个部分：
一.通过"bottom-up"策略成功将J(?)rgensen-Hayashi催化剂嵌入手性多孔有机材料骨架,合成了手性多孔有机材料JH-CPP,并实现了该材料在多相催化不对称Michael加成反应中的应用。该材料高的比表面积(881m2／g)、开放的和相互交叉贯通的孔道结构使得其在催化不对称Michael加成反应时有着和均相催化剂相媲美的催化效果,并且该材料可以循环使用四次,产物的ee值没有降低(97-99%ee)。
二.进一步拓展了JH-CPP材料在催化硝基甲烷对α,β-不饱和醛的不对称Michael加成反应中的应用。研究发现,JH-CPP材料在催化该反应时,除了有着和均相催化剂相媲美的催化效果外,它还优越于采用传统方式固载的J(?)rgensen-Hayashi催化剂,并且该材料可以循环使用六次,产物的ee值没有任何降低(95-96%ee)。
三.通过"bottom-up"策略成功将MacMillan催化剂嵌入手性多孔有机材料骨架,实现了该材料在多相催化不对称Diels-Alder反应中的应用。通过调节不同的结构性砌块合成了三种具有不同比表面积的材料(Mac-CPP-1, Mac-CPP-2, Mac-CPP-3),考察了材料的结构一性质一催化活性之间的关系。
四.通过“自负载”策略合成了MacMillan聚合物催化剂(Mac-ChiOSP),并研究了其在催化不对称Diels-Alder反应中的应用。研究发现该手性材料可以实现均相条件下催化反应,多相条件下回收循环。与“后合成”策略得到的固载催化剂相比,通过“自负载”策略合成的多聚MacMillan催化剂有着均一分布的和高密度的催化活性位,再加上这种均相条件下催化反应的特性,使得该材料有着和均相催化剂同等的催化活性和对映选择性。并且该材料可以循环使用三次,产物的ee值没有降低(86-90%ee for endo,84-88%ee for exo)。
Due to their inherent porosity, large specific surface area, light weight, and easy functionalization at the molecular level, porous organic polymers have recently received significant attention for potential applications in gas storage/separation, light-harvesting, sensoring, and heterogeneous catalysis. Especially, the construction of functional porous organic polymers via bottom-up strategy for heterogeneous catalysis has made tremendous development in recent years. The reported research works in this field are mainly focused on the embedding of the organometallics into the polymers, or the encapsulation of the metal particles into the porous organic polymers. Nevertheless, to date, the embedding of chiral organocatalysts into the frameworks of the porous organic polymers via bottom-up strategy has been not reported yet. In this context, with the rapid development of asymmetric organocatalysis, construction of organocatalysts embedded chiral porous organic polymers via bottom-up strategy for the heterogeneous asymmetric organocatalysis will be a promising and challenging research issue.
Accordingly, the main research contents of this thesis is to design, synthesize and characterize the chiral porous organic polymers based on chiral organocatalysts (J(?)rgensen-Hayashi catalyst and MacMillan catalyst), and utilize them in the heterogeneous asymmetric organocatalysis. The main achievements of this thesis could be divided into the following four parts:
1. The Jorgensen-Hayashi catalyst has been successfully embedded into a nanoporous polymer via the bottom-up strategy. The obtained JH-CPP polymer has been utilized as a highly efficient heterogeneous organocatalyst for the asymmetric Michael addition reaction. Owing to the high BET surface area (881m2/g), as well as the widely pervasive and interconnected pores, JH-CPP possesses comparable activity and enantioselectivity with the homogeneous JH catalyst. Furthermore, the JH-CPP catalyst can be reused for at least four times with no decrease of enantioselectivity (97-99%ee).
2. To further expanding the catalytic application of JH-CPP to other asymmetric reactions, we have also applied JH-CPP as the heterogeneous organocatalyst in the asymmetric Michael addition reaction of nitromethane with a, p-unsaturated aldehydes. The JH-CPP catalyst shows comparable catalytic efficiency with the homogeneous JH catalyst, and can be reused for at least six times with no decrease of enantioselectivity (95-96%ee). Notably, the catalytic efficiency of JH-CPP catalyst is superior to that of the traditional immobilized J(?)rgensen-Hayashi catalyst.
3. The MacMillan catalyst has been successfully embedded into nanoporous polymers via the bottom-up strategy, and the obtained polymers have been applied as highly efficient heterogeneous organocatalysts for the asymmetric Diels-Alder reaction. The specific surface areas of the three MacMillan catalyst-embedded chiral porous polymers (Mac-CPP-1, Mac-CPP-2, Mac-CPP-3) can be adjusted by changing the size of the structural building blocks. We have also investigated the structure-property-catalytic activity relationship of these MacMillan catalyst-embedded chiral porous polymers.
4. We have synthesized a "self-supported" polymeric MacMillan catalyst (Mac-ChiOSP), which can be applied as an efficient catalyst for homogeneous organocatalysis and heterogeneous recycling for the asymmetric Diels-Alder reaction. In comparison with thosee immobilized MacMillan catalysts, this "self-supported" polymeric MacMillan catalyst possesses homogeneously-distributed and highly-concentrated catalytic sites. This advantage together with the homogeneous catalytic nature ensured its excellent catalytic ability. Furthermore, the heterogeneous catalyst can be reused for at least three times with no decrease of enantioselectivity (86-90%ee for endo,84-88%for exo).
引文
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