本文選題：芳烴氟 + 芳基腈　； 參考：《華東理工大學》2017年碩士論文

【摘要】：由于二芳基甲烷是重要的有機合成砌塊,使得二芳基甲烷在醫(yī)藥、染料和超分子中有著廣泛的應用,因此研究新的二芳基甲烷的合成方法受到越來越多的關(guān)注。另外,氰基很容易轉(zhuǎn)化成其他的官能團,因此芳基腈類化合物是應用廣泛的反應中間體。目前,碳氟鍵的斷裂及其官能團化是有機化學的一大研究熱點。本論文研究了在溫和條件下芳烴的碳氟鍵的斷裂及其氰基化,高效地合成了鄰氰基二芳基甲烷類化合物。另外,在論文的第二部分我們還研究了β,β-二溴烯烴的叔烷基化反應。兩個系列共合成了 49個目標化合物。在第二章中,我們研究了在室溫條件下,以無水四氫呋喃為溶劑,LDA為堿,通過芳基腈和芳烴氟反應生成鄰氰基二芳基甲烷的合成方法。該反應具有較好的底物拓展性。我們還將該反應底物拓展到氯苯和溴苯,結(jié)果表明反應依然能順利進行。我們同時對反應的機理進行了初步的探索,并提出了可能的反應機理。本章共合成了 31個結(jié)構(gòu)新穎的鄰氰基二芳基甲烷類目標化合物。在第三章中,我們研究了兩個新穎的反應體系:(1)在室溫條件下,以CuCN為催化劑,無水四氫呋喃為溶劑,通過叔丁基氯化鎂與多種β,β-二溴烯烴反應,最終以90%左右的收率得到E-式和Z-式兩種異構(gòu)體的單取代目標產(chǎn)物;(2)在甲苯回流條件下,無需過渡金屬催化,實現(xiàn)了叔丁基氯化鎂與多種β,β-二溴烯烴反應,結(jié)果能以中等收率得到單取代的還原產(chǎn)物。本章共合成了 18個目標化合物。
[Abstract]:As diarylmethane is an important organic synthetic block, diaryl methane has been widely used in medicine, dyes and supramolecular, so more and more attention has been paid to the research of new synthesis method of diaryl methane. In addition, cyanide groups are easily converted into other functional groups, so arylonitrile compounds are widely used as reaction intermediates. At present, the fracture of carbon-fluorine bond and its functionalization is a hot spot in organic chemistry. In this paper, the cleavage of carbon-fluorine bond and cyanoylation of aromatics under mild conditions were studied, and the o-cyano-diarylmethane compounds were synthesized efficiently. In addition, in the second part of the thesis, we studied the tert-alkylation of 尾, 尾 -dibromoalkenes. A total of 49 target compounds were synthesized from two series. In chapter 2, we studied the synthesis of o-cyanodiarylmethane by the reaction of arylonitrile and aromatic fluorine using anhydrous tetrahydrofuran as solvent LDA as base at room temperature. This reaction has good substrate expansibility. We also extended the substrate to chlorobenzene and bromobenzene, and the results showed that the reaction could still proceed smoothly. At the same time, we explored the reaction mechanism and put forward the possible reaction mechanism. In this chapter, a total of 31 novel o-cyano-diarylmethane compounds were synthesized. In chapter 3, we studied two novel reaction systems: (1) in the presence of CuCN as catalyst and anhydrous tetrahydrofuran as solvent, tert Ding Ji magnesium chloride reacted with various 尾, 尾 -dibromoolefins at room temperature. Finally, the monosubstituted target products of E- and Z- isomers were obtained in 90% yield. (2) under the reflux of toluene, the reaction of tert Ding Ji magnesium chloride with various 尾, 尾 -dibromoolefins was realized without transition metal catalysis. Results the monosubstituted reduction products could be obtained in medium yield. In this chapter, 18 target compounds were synthesized.
【學位授予單位】：華東理工大學
【學位級別】：碩士
【學位授予年份】：2017
【分類號】：O621.3

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