芳香羧酸脱羧碘代及芳烃直接三氟甲基化反应研究

发布时间：2018-09-04 17:56

【摘要】：官能团化的芳烃广泛存在医药、农药、以及多功能材料中,因此芳烃的官能团化反应具有较高的研究价值。碘代芳烃与三氟甲基取代芳烃由于其特殊的物理、化学性质,在很多领域发挥着重要的作用。本论文研究内容包括芳香羧酸脱羧反应一步合成碘代芳烃及芳烃直接三氟甲基化合成三氟甲基取代芳烃。具体研究内容如下:(1)以廉价易得的芳香羧酸为底物,以碘代琥珀酰亚胺(NIS)为碘源,微量的Pd(OAc)2为催化剂,通过控制反应条件,选择性得到单碘代芳烃与双碘代芳烃。反应可以扩量至克级,且催化剂用量可进一步降低至0.66 mol%。该方法具有高效实用、操作简单等优点。本课题的工作为碘代芳烃的合成提供了高效、简单的新途径。(2)氧化石墨烯作为一种新兴材料,具有特殊的物理化学性质,其在有机化学领域已有广泛的应用,成为目前的研究热点之一。本文以三氟甲基亚磺酸钠为三氟甲基化试剂,通过加入氧化石墨烯促进芳烃C-H键活化,实现了芳烃的直接三氟甲基化。该方法具有无金属参与、原料廉价易得、操作简单等优点,为合成三氟甲基取代芳烃提供了新途径。
[Abstract]:Functional aromatics are widely used in medicine, pesticides, and multifunctional materials, so the functional reactions of aromatics have high research value. Iodinated aromatics and trifluoromethyl substituted aromatics play an important role in many fields because of their special physical and chemical properties. In this paper, one step synthesis of iodide aromatics and direct trifluoromethylation of aromatic aromatics to trifluoromethyl substituted aromatics were studied. The main contents are as follows: (1) monoiodinated aromatic hydrocarbons and diiodide aromatics were selectively obtained by controlling the reaction conditions, using cheap and readily available aromatic carboxylic acids as substrate, iodinated succinimide (NIS) as iodine source and trace Pd (OAc) _ 2 as catalyst. The reaction can be expanded to g level, and the amount of catalyst can be further reduced to 0.66 mol%.. This method has the advantages of high efficiency and practicality, simple operation and so on. This work provides a new and efficient way for the synthesis of iodide aromatics. (2) as a new material, graphene oxide has special physical and chemical properties and has been widely used in the field of organic chemistry. It has become one of the research hotspots. In this paper, the direct trifluoromethylation of aromatics was realized by adding graphene oxide to promote the activation of C-H bond of aromatics with sodium trifluoromethylene sulfonate as trifluoromethylation reagent. The method has the advantages of no metal participation, cheap raw materials and simple operation, which provides a new way for the synthesis of trifluoromethyl substituted aromatics.
【学位授予单位】：湘潭大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.25

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