Title

1.利用微波促進醛類與二硒醚之耦合反應合成硒酯化合物 2.二叔丁基過氧化物與三氯化鋁促進缺電子的含氮雜環進行硒化反應

Translated Titles

1.Microwave-Promoted Synthesis of Selenoesters Through Coupling Reaction of Aldehydes with Diselenides 2.DTBP/AlCl3 Mediated Selenation of Electron-Deficient N-Heterocycles

Authors

陳冠宇

Key Words

碳-硒鍵生成 ; 硒化反應 ; C-Se bonds ; selenation

PublicationName

中興大學化學系所學位論文

Volume or Term/Year and Month of Publication

2016年

Academic Degree Category

碩士

Advisor

李進發

Content Language

繁體中文

Chinese Abstract

本論文的第一部分利用微波促進二叔丁基過氧化物在無金屬以及無溶劑下,使醛類上的碳-氫鍵硒化,此方法反應時間只需30分鐘,系統的官能基容忍性非常廣泛,包括有溴基、三氟甲基、氯基,還有噻吩、呋喃等雜環官能基。二芳香基二硒醚和二烷基二硒醚都能與醛類反應提供產率不錯的硒酯化合物。 本論文的第二部分,是描述關於缺電子含氮雜環(異喹?和喹?)的硒化反應,在催化劑三氯化鋁和氧化劑二叔丁基過氧化物的幫助下,將異喹(喹?)與二硒化合物進行碳-硒鍵耦合反應。這也是第一個使用二硒化合物直接將異喹?和喹?做硒化反應的報導。

English Abstract

In the first part of this thesis, microwave-assisted DTBP-promoted C-H selenation of aldehydes with diselenides under metal-free and solvent-free conditions. This approach enables the synthesis of selenoesters in short reaction time (30 min). The system shows good functional group compatiblility, functional groups including bromo, trifluoromethyl, chloro and heterocyclo-containing moieties including thiophene and furan are all tolerated by the reaction conditions employed. Both diaryl and dialkyl diselenides reacted smoothly with aldehydes to provide selenoesters in good to excellent yields. In the second part of this thesis, a selenation of electron-deficient N-heterocycles (isoquinoline and quinoline) have been described. Isoquinoline (quinoline) and diselenides leading to C-Se coupling reaction has been accomplished using AlCl3 as the catalyst in the presence of oxidant DTBP. To the best of our knowledge, this is the first example of direct selenation of isoquinoline and quinoline with diselenides.

Topic Category 基礎與應用科學 > 化學
理學院 > 化學系所
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