环碳酸酯的合成研究
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摘要
在当今化学研究领域,二氧化碳作为原料合成的环碳酸酯是一类极其重要的化合物,其可以作为极性非质子溶剂、有机合成的中间体以及聚合物的前体等。本论文以环碳酸酯的不对称合成及多组分合成为研究内容,包括以下四章：
第一章：综述了环碳酸酯的应用及合成方法,并对二氧化碳与环氧化合物偶联反应合成环碳酸酯的最新进展进行了简要介绍,本章最后简要介绍了聚合物催化剂在不对称反应中的设计及应用。
第二章：基于“均相催化,两相分离”这样一个概念设计合成了四种多手性中心的聚BINOL-SalenCo化合物,并对合成过程中遇到的问题进行了详细的介绍和讨论。
第三章：将设计合成的聚BINOL-SalenCo化合物应用到催化二氧化碳与环氧化合物的不对称环加成反应以及环氧丙烷的动力学水解拆分反应,同时研究了不同手性催化剂、共催化剂、抗衡离子、反应温度对生成光活性环碳酸酯的ee值的影响,研究显示手性的Binol片段对于聚合物催化剂的光学选择性有着重要的影响,最后我们还对催化剂的循环使用进行了考察,结果显示该类催化剂在没有观察到活性及光学选择性明显降低的情况下,可以重复使用十次。
第四章：在对二氧化碳与环氧化合物环加成反应机理理解的基础上,我们由Darzens缩合反应出发,在反应过程中引入二氧化碳气体,合成得到了环碳酸酯,从而将该合成反应设计成为由醛类衍生物,α-溴代苯乙酮衍生物,二氧化碳多组分一锅法反应合成多取代的环碳酸酯,同时研究了不同的碱、有机溶剂、反应温度、底物对产物选择性及产率的影响。结果显示该合成方法的优点在于该反应可以在非常温和的条件下(1 atm CO2,35℃),在非常短的反应时间内(10 min)得到环碳酸酯产物。
Cyclic carbonates, as one of products of CO2 chemistry, are attractive and important compounds in a variety of chemical research fields, such as polar aprotic solvent, intermediate in organic synthesis, precursors for polymeric materials such as polycarbonates。This thesis aims at the studies on the asymmetric synthesis and multi-component synthesis of cyclic carbonate, which consists of the following four chapters.
Chapter 1:The application and synthesis of cyclic carbonate are reviewed, and the development in the green synthesis of cyclic carbonate via CO2 cycloaddition to epoxide is briefly introducted. The design and application of polymer catalyst on the asymmetric synthesis also are concluded in this chapter.
Chapter 2:Based on the concept of "one-phase catalysis and two-phase separation", we developed four new polymer BINOL-Salen-Co (III)X catalysts with an auxiliary chiral site, and problems encountered in the synthesis of the catalyst are presented and discussed in detail.
Chapter 3:Four new chiral polymers of BINOL-Salen-cobalt (III) salt complexes have been applied to the direct fabrication of chiral propylene carbonate from racemic propylene oxide and the hydrolytic kinetic resolution of racemic propylene. The experiment investigated the effect of different chiral catalyst, co-catalyst, counterious, reaction temperature in chiral cyclic carbonate formation. The chirality of the BINOL fragment has an important influence on the optical selectivity of Salen-Co(III)X complexes. The catalysts could be readily recovered and be repeatedly used without loss of either activity or enantioselectivity.
Chapter 4:Inspired by the mechanism of the Darzens reaction and based on mechanism considerations of cyclic carbonate synthesis, we design a three-component cyclization reaction for polysubstituted cyclic carbonate synthesis in a single operation from phenacyl bromide, CO2, and aldehyde using LDA as a base. The experiment investigated the effect of base, solvent, reaction temperature, substrate on the selection and yield of cyclic carbonate formation. This novel, efficient synthesis of polysubstituted cyclic carbonates was achieved under mild conditions (1 atm,35℃) in reasonable yields with a reaction time of only ten minutes.
第一章：综述了环碳酸酯的应用及合成方法,并对二氧化碳与环氧化合物偶联反应合成环碳酸酯的最新进展进行了简要介绍,本章最后简要介绍了聚合物催化剂在不对称反应中的设计及应用。
第二章：基于“均相催化,两相分离”这样一个概念设计合成了四种多手性中心的聚BINOL-SalenCo化合物,并对合成过程中遇到的问题进行了详细的介绍和讨论。
第三章：将设计合成的聚BINOL-SalenCo化合物应用到催化二氧化碳与环氧化合物的不对称环加成反应以及环氧丙烷的动力学水解拆分反应,同时研究了不同手性催化剂、共催化剂、抗衡离子、反应温度对生成光活性环碳酸酯的ee值的影响,研究显示手性的Binol片段对于聚合物催化剂的光学选择性有着重要的影响,最后我们还对催化剂的循环使用进行了考察,结果显示该类催化剂在没有观察到活性及光学选择性明显降低的情况下,可以重复使用十次。
第四章：在对二氧化碳与环氧化合物环加成反应机理理解的基础上,我们由Darzens缩合反应出发,在反应过程中引入二氧化碳气体,合成得到了环碳酸酯,从而将该合成反应设计成为由醛类衍生物,α-溴代苯乙酮衍生物,二氧化碳多组分一锅法反应合成多取代的环碳酸酯,同时研究了不同的碱、有机溶剂、反应温度、底物对产物选择性及产率的影响。结果显示该合成方法的优点在于该反应可以在非常温和的条件下(1 atm CO2,35℃),在非常短的反应时间内(10 min)得到环碳酸酯产物。
Cyclic carbonates, as one of products of CO2 chemistry, are attractive and important compounds in a variety of chemical research fields, such as polar aprotic solvent, intermediate in organic synthesis, precursors for polymeric materials such as polycarbonates。This thesis aims at the studies on the asymmetric synthesis and multi-component synthesis of cyclic carbonate, which consists of the following four chapters.
Chapter 1:The application and synthesis of cyclic carbonate are reviewed, and the development in the green synthesis of cyclic carbonate via CO2 cycloaddition to epoxide is briefly introducted. The design and application of polymer catalyst on the asymmetric synthesis also are concluded in this chapter.
Chapter 2:Based on the concept of "one-phase catalysis and two-phase separation", we developed four new polymer BINOL-Salen-Co (III)X catalysts with an auxiliary chiral site, and problems encountered in the synthesis of the catalyst are presented and discussed in detail.
Chapter 3:Four new chiral polymers of BINOL-Salen-cobalt (III) salt complexes have been applied to the direct fabrication of chiral propylene carbonate from racemic propylene oxide and the hydrolytic kinetic resolution of racemic propylene. The experiment investigated the effect of different chiral catalyst, co-catalyst, counterious, reaction temperature in chiral cyclic carbonate formation. The chirality of the BINOL fragment has an important influence on the optical selectivity of Salen-Co(III)X complexes. The catalysts could be readily recovered and be repeatedly used without loss of either activity or enantioselectivity.
Chapter 4:Inspired by the mechanism of the Darzens reaction and based on mechanism considerations of cyclic carbonate synthesis, we design a three-component cyclization reaction for polysubstituted cyclic carbonate synthesis in a single operation from phenacyl bromide, CO2, and aldehyde using LDA as a base. The experiment investigated the effect of base, solvent, reaction temperature, substrate on the selection and yield of cyclic carbonate formation. This novel, efficient synthesis of polysubstituted cyclic carbonates was achieved under mild conditions (1 atm,35℃) in reasonable yields with a reaction time of only ten minutes.
引文
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