【摘要】：過渡金屬銅催化的三氟甲基化反應為有機分子中引入三氟甲基提供了新的思路而成為近年來方法學研究的熱點內(nèi)容。本論文首先綜述了銅催化的三氟甲基化反應發(fā)展歷史和現(xiàn)狀,列舉了銅參與的碳原子上引入三氟甲基的反應實例,將過渡金屬參與的三氟甲基化反應真正應用于有機合成的關鍵在于發(fā)展高效溫和且廉價的催化體系,構建各種雜化方式的C-CF3鍵。本論文主要探索了銅參與三氟甲基引入反應,全文分為兩個部分:針對前人報道的銅參與的烷基鹵代物的三氟甲基化反應無法有效解決烷基氯代物三氟甲基化的問題,我們發(fā)現(xiàn)在光和銅催化下可以順利實現(xiàn)烷基氯代物的三氟甲基化反應。該反應的優(yōu)點是宮能團兼容性好,底物適應面廣,反應條件溫和,可操作性強。新方法為烷基上引入三氟甲基提供了有效的途徑,豐富了烷基含三氟甲基的生物活性分子的合成方。針對三氟甲基炔丙醇衍生物合成困難這一挑戰(zhàn),我們設計了銅催化的三氟乙基插入炔基高價碘試劑的反應。該反應的優(yōu)點是官能團兼容性好,反應條件溫和,操作簡單。新方法不僅提供了引入三氟甲基的有效途徑,豐富了三氟甲基化合物的底物范圍,還為二級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.
【學位授予單位】：合肥工業(yè)大學
【學位級別】：碩士
【學位授予年份】：2017
【分類號】：O621.251

【參考文獻】

相關期刊論文 前1條

1 王光祖;赫俠平;戴建軍;許華建;;銅促進的三氟甲基化反應研究進展[J];有機化學;2014年05期

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本文編號：2244422