苯并咪唑类手性卡宾前体的合成及应用

发布时间：2018-01-03 15:21

本文关键词：苯并咪唑类手性卡宾前体的合成及应用　出处：《上海工程技术大学》2016年硕士论文　论文类型：学位论文

【摘要】：N-杂环卡宾的研究是一个很广的领域,因为其在反应中扮演催化剂的角色而被我们熟知,其优点不言而喻,具有强富电性,结构的易修饰性,强配位能力等特点,特别突出的是N-杂环卡宾在金属催化领域有着不可替代的作用。对于手性的N-杂环卡宾,我们通过对卡宾环上的碳原子或者氮原子上的取代基团选择,来优化手性N-杂环卡宾的空间位阻,电子的性质,以及手性的环境,近年来我们课题组致力于对新型卡宾的开发与研究,例如铜-氮杂环卡宾的金属络合物合成α-氨基硼酸,以及钯-氮杂环卡宾的金属络合物合成二芳基酮类化合物。而上述N-杂环卡宾配体的合成与应用忽略了一个重要的性质—手性。手性的N-杂环卡宾的研究是近年来手性催化领域的研究热点,其被应用在不对称催化反应越来越广泛。本论文研究的苯并咪唑类手性卡宾是N-杂环卡宾大家庭的一类,本文设计并合成新型苯并咪唑类手性卡宾前体7例,同时拓展其在不对称催化反应的应用。本论文主要工作包括以下两个方面:一、新型苯并咪唑类手性卡宾前体的合成:我们设计了一系列新型苯并咪唑类手性卡宾前体。最终合成得到7例新型手性氮杂环卡宾前体,其中卡宾环上的碳原子或者氮原子上的取代基团都具有一定代表性,这些化合物均得到1H NMR、13C NMR、HR-MS等波谱的表征。二、新型苯并咪唑类手性卡宾前体在不对称反应中催化应用利用合成的新型苯并咪唑类手性卡宾前体和铜金属络合物合成得到硼酸酯类化合物。所有化合物均得到了1H NMR、13C NMR、HR-MS、HPLC等波谱的表征。
[Abstract]:The study of N-heterocyclic carbene is a wide field, which is known to us for its role as catalyst in the reaction. Its advantages are self-evident, with strong electrical properties, easy modification of the structure. Especially, N-heterocyclic carbene plays an irreplaceable role in the field of metal catalysis, especially for chiral N-heterocyclic carbene. We optimize the steric hindrance of chiral N-heterocyclic carbene, the properties of electrons, and the chiral environment by selecting the carbon atoms on the carbene ring or the substituents on the nitrogen atoms. In recent years, our research group has been devoted to the development and research of novel carbenes, such as the synthesis of 伪 -aminoboric acid by the metal complexes of copper-aza-heterocyclic carbenes. The synthesis and application of the N-heterocyclic carbene ligands neglect an important property, chirality. The study of chiral N-heterocyclic carbene is that of N-heterocyclic carbene. In recent years, the research focus in the field of chiral catalysis. In this paper, the chiral carbenes of benzimidazoles are a kind of N- heterocyclic carbene family. Seven cases of novel benzimidazole chiral carbene precursors were designed and synthesized. At the same time, its application in asymmetric catalytic reaction is expanded. The main work of this thesis includes the following two aspects: 1. Synthesis of novel benzimidazole chiral carbene precursors: we designed a series of novel benzimidazole chiral carbene precursors. The carbon atoms on carbene ring and the substituents on nitrogen atoms are all representative. These compounds are characterized by 1H-NMR-13C NMR-HR-MS spectra. Synthesis of novel benzimidazole Chiral carbene precursors by Catalytic Application in asymmetric reactions Synthesis of novel benzimidazole Chiral carbene precursors and Copper Metal complexes have been used to synthesize borate esters. All the compounds have been obtained. 1H. NMR. Characterization of 13C NMR-HR-MSX HPLC.
【学位授予单位】：上海工程技术大学
【学位级别】：硕士
【学位授予年份】：2016
【分类号】：O626.23

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