芳基叔胺的合成以及含叔烷基的偕二氟烯烃的合成

发布时间：2018-02-05 19:05

本文关键词： 氟代芳烃氨基化反应 α-三氟甲基苯乙烯叔烷基格氏试剂含叔烷基的偕二氟苯乙烯　出处：《华东理工大学》2017年硕士论文　论文类型：学位论文

【摘要】：在有机分子中引入氟原子通常会使母体化合物的化学、物理和生物学性质发生明显的改变,因此有机氟化合物在药理学,制药,农业和材料科学领域越来越受到重视。但随着含氟有机化合物的大量使用,它们对环境污染问题日显突出。碳氟键的高键能使其难以断裂,因此寻找简捷高效的方法进行碳氟键的选择性断裂受到有机合成化学家们的广泛关注。本论文以温和、高效断裂碳氟键为出发点,研究了氟代芳烃的叔胺化反应和α-三氟甲基苯乙烯类化合物与大位阻叔烷基格氏试剂的反应。第二章研究了一种无过渡金属催化的碳氮偶联反应。该方法以氟代芳烃和仲胺为底物,在n-BuLi和四氢呋喃条件下经苯炔中间体发生碳氮偶联反应生成芳基叔胺化合物。该方法原料廉价易得,操作简单,反应收率高。第三章研究了在室温和氰化亚铜条件下α-三氟甲基苯乙烯类化合物与叔烷基格氏试剂的偶联反应,反应经SN2'机理进行,选择性的合成了一系列结构新颖的含叔烷基的偕二氟苯乙烯类化合物。
[Abstract]:The introduction of fluorine atoms in organic molecules usually results in significant changes in the chemical, physical and biological properties of the parent compounds, so organic fluorines are used in pharmacology and pharmaceuticals. More and more attention has been paid to the fields of agriculture and material science. However, with the extensive use of fluorinated organic compounds, the environmental pollution problem becomes more and more serious. The high bond energy of carbon-fluorine bond makes it difficult to break. Therefore, the search for a simple and efficient method for the selective cleavage of carbon-fluorine bonds has attracted wide attention of organic synthetic chemists. In this paper, mild and efficient breakage of carbon-fluorine bonds is the starting point. The tertiary amination of fluorinated aromatics and the reaction of 伪 -trifluoromethyl styrene with large steric hindrance tert-alkyl Grignard reagent were studied. In chapter 2, a carbon-nitrogen coupling reaction without transition metal catalysis was studied. Substituted aromatic hydrocarbons and secondary amines as substrates. Under the conditions of n-BuLi and tetrahydrofuran, aryl tertiary amines were synthesized by carbon-nitrogen coupling reaction of benzene alkyne intermediates. This method is cheap and easy to obtain and easy to operate. In chapter 3, the coupling reaction of 伪 -trifluoromethyl styrene with tert-alkyl Grignard reagent at room temperature and cuprous cyanide was studied, and the reaction was carried out by SN2 'mechanism. A series of novel tert-alkyl-containing difluorobenzene compounds were selectively synthesized.
【学位授予单位】：华东理工大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.25

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