铜催化的三氟甲基化反应
发布时间：2018-09-16 18:52
【摘要】：过渡金属铜催化的三氟甲基化反应为有机分子中引入三氟甲基提供了新的思路而成为近年来方法学研究的热点内容。本论文首先综述了铜催化的三氟甲基化反应发展历史和现状,列举了铜参与的碳原子上引入三氟甲基的反应实例,将过渡金属参与的三氟甲基化反应真正应用于有机合成的关键在于发展高效温和且廉价的催化体系,构建各种杂化方式的C-CF3键。本论文主要探索了铜参与三氟甲基引入反应,全文分为两个部分:针对前人报道的铜参与的烷基卤代物的三氟甲基化反应无法有效解决烷基氯代物三氟甲基化的问题,我们发现在光和铜催化下可以顺利实现烷基氯代物的三氟甲基化反应。该反应的优点是宫能团兼容性好,底物适应面广,反应条件温和,可操作性强。新方法为烷基上引入三氟甲基提供了有效的途径,丰富了烷基含三氟甲基的生物活性分子的合成方。针对三氟甲基炔丙醇衍生物合成困难这一挑战,我们设计了铜催化的三氟乙基插入炔基高价碘试剂的反应。该反应的优点是官能团兼容性好,反应条件温和,操作简单。新方法不仅提供了引入三氟甲基的有效途径,丰富了三氟甲基化合物的底物范围,还为二级三氟炔丙醇的合成提供了方法。
[Abstract]:The transition metal copper catalyzed trifluoromethylation provides a new idea for the introduction of trifluoromethyl into organic molecules and has become a hot topic in recent years. In this paper, the development history and present situation of copper catalyzed trifluoromethylation are reviewed, and the examples of the introduction of trifluoromethyl to the carbon atom in which copper is involved are listed. The key to the application of transition metal trifluoromethylation in organic synthesis lies in the development of efficient, mild and inexpensive catalytic systems and the construction of various hybrid C-CF3 bonds. In this paper, the participation of copper in the trifluoromethyl introduction reaction is mainly explored. The whole paper is divided into two parts: the trifluoromethylation of alkyl halides reported by previous reports cannot effectively solve the problem of trifluoromethylation of alkyl chlorides. We found that trifluoromethylation of alkyl chlorides can be successfully realized under the catalysis of light and copper. The advantages of the reaction are good compatibility, wide substrate adaptation, mild reaction conditions and strong maneuverability. The new method provides an effective way to introduce trifluoromethyl to alkyl and enriches the synthetic formula of bioactive molecules containing trifluoromethyl alkyl. In view of the difficulty in the synthesis of trifluoromethyl propargyl alcohol derivatives, a copper catalyzed trifluoroethyl iodide insertion reaction was designed. The advantages of the reaction are good functional compatibility, mild reaction conditions and simple operation. The new method not only provides an effective way to introduce trifluoromethyl, enriches the substrate range of trifluoromethyl compounds, but also provides a method for the synthesis of secondary trifluoropropargyl alcohol.
【学位授予单位】：合肥工业大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.251
本文编号：2244422
[Abstract]:The transition metal copper catalyzed trifluoromethylation provides a new idea for the introduction of trifluoromethyl into organic molecules and has become a hot topic in recent years. In this paper, the development history and present situation of copper catalyzed trifluoromethylation are reviewed, and the examples of the introduction of trifluoromethyl to the carbon atom in which copper is involved are listed. The key to the application of transition metal trifluoromethylation in organic synthesis lies in the development of efficient, mild and inexpensive catalytic systems and the construction of various hybrid C-CF3 bonds. In this paper, the participation of copper in the trifluoromethyl introduction reaction is mainly explored. The whole paper is divided into two parts: the trifluoromethylation of alkyl halides reported by previous reports cannot effectively solve the problem of trifluoromethylation of alkyl chlorides. We found that trifluoromethylation of alkyl chlorides can be successfully realized under the catalysis of light and copper. The advantages of the reaction are good compatibility, wide substrate adaptation, mild reaction conditions and strong maneuverability. The new method provides an effective way to introduce trifluoromethyl to alkyl and enriches the synthetic formula of bioactive molecules containing trifluoromethyl alkyl. In view of the difficulty in the synthesis of trifluoromethyl propargyl alcohol derivatives, a copper catalyzed trifluoroethyl iodide insertion reaction was designed. The advantages of the reaction are good functional compatibility, mild reaction conditions and simple operation. The new method not only provides an effective way to introduce trifluoromethyl, enriches the substrate range of trifluoromethyl compounds, but also provides a method for the synthesis of secondary trifluoropropargyl alcohol.
【学位授予单位】：合肥工业大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.251
【参考文献】
相关期刊论文 前1条
1 王光祖;赫侠平;戴建军;许华建;;铜促进的三氟甲基化反应研究进展[J];有机化学;2014年05期
，本文编号：2244422
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