請用此 Handle URI 來引用此文件: http://hdl.handle.net/11455/90640
標題: 1. Syntheses of Selenide Ethers and Thioesters from Methyl Arenes Through sp³ C-H Functionalization 2. Peracetic Acid-Mediated sp² C-H Selenation of Methyl Arenes
1. 通過sp³碳-氫鍵功能化合成硒醚化合物與硫酯化合物 2. 過氧醋酸促進甲基芳香環進行sp²碳-氫鍵之硒化反應
作者: 謝秉桉
Ping- An Hsieh
關鍵字: Selenide Ethers
Thioesters
Selenation
硒醚化合物
硫酯化合物
硒化反應
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摘要: In the first part of this thesis, A DTBP-promoted, operationally simple, metal-free and solvent-free C-Se and C-S bond formation through a sp³ C-H functionalization of methyl arenes with diselenides and disulfides is described. Diselenides and disulfides containing various functionalities were coupled smoothly with a broad spectrum of methyl arenes, afforded the corresponding selenide ethers and thioesters in moderate to good yields. This system shows good functional group tolerance, functional groups including chloro, bromo, trifluoromethyl and iodo were tolerated by the reaction conditions. Methyl heteroaryl compounds also coupled well with both of diselenides and disulfides to provide corrosponding selenide ether and thioester respectively. In the second part of this thesis, AcOOH promoted C-Se coupling reaction of arenes with diselenides under metal free and solvent free conditions has been described. The resulting selenide ethers were obtained in good to excellent yields. Very recently, we have reported a DTBP (di-tert-butyl peroxide) promoted syntheses of selenide ethers from methyl arenes via sp³ C-H functionalization. Now, we have observed an interesting oxidant and herein report the AcOOH mediated sp² C-H selenation of methyl arenes under metal free and solvent free conditions.
本論文的第一部分是描述在不須金屬觸媒與溶劑的情況下,二叔丁基過氧化物促進甲基芳香環進行sp³碳-氫鍵功能化,並與二硒、二硫化合物生成碳-硒與碳-硫鍵。包含各種官能基的二硒或二硫化合物皆可順利與甲基芳香環進行耦合反應,並可生成中等至良好產率的硒醚化合物或硫酯化合物。此系統具有良好的官能基容忍性,包括氯基、溴基、三氟甲基、和碘基皆適用於此反應條件。甲基芳香雜環化合物也可與二硒、二硫化合物進行耦合反應,且分別生成硒醚化合物與硫酯化合物。 論文的第二部分是描述在不須金屬觸媒與溶劑的情況下,過氧醋酸促進甲基芳香環與二硒化合物進行碳-硒鍵耦合反應。結果顯示可獲得硒醚化合物且具良好至極佳的產率。之前,我們是開發二叔丁基過氧化物促進甲基芳香環進行sp³碳-氫鍵功能化合成硒醚化合物,而現在我們發現一個有趣的氧化劑過氧醋酸,其可以促使甲基芳香環進行sp²碳-氫鍵硒化,且不須添加任何過渡金屬觸媒與溶劑。
URI: http://hdl.handle.net/11455/90640
文章公開時間: 2017-08-13
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