亞硝鎓離子催化芳香烴氧化氯化反應

Please use this identifier to cite or link to this item: https://ir.lib.ncu.edu.tw/handle/987654321/97598

Title:	亞硝鎓離子催化芳香烴氧化氯化反應
Authors:	許茹菁;Hsu, Ju-Ching
Contributors:	化學學系
Keywords:	亞硝鎓離子;芳香烴氧化;氯化反應
Date:	2025-08-27
Issue Date:	2025-10-17 11:40:04 (UTC+8)
Publisher:	國立中央大學
Abstract:	本研究開發出一種操作簡便且環境友善的芳香環氯化方法，適用於多種電子密度高的芳香族化合物。該反應以硝酸作為亞硝鎓離子 (nitrosonium, NO⁺) 的來源，氯化鈉 (sodium chloride, NaCl) 作為氯梨子來源，並以分子氧作為終端氧化劑，產生過氧化氫 (hydrogen peroxide, H2O2) 為副產物。反應條件溫和，無需使用過渡金屬或有機催化劑，亦不涉及具高危險性的傳統氯化劑，具有良好的操作安全性與實用性。多種芳香環化合物均能有效進行選擇性氯化，並獲得良好產率。反應機構的研究顯示，本反應是經由亞硝鎓離子起始的單電子氧化芳香烴，形成芳基自由基中間體。該方法亦成功應用於藥物中間體的合成，包括甲氧氯普胺 (metoclopramide) 與羥氯二氮平 (oxazepam) 之前驅物，展現其於有機合成與藥物開發領域的潛在價值。 ;In this thesis, I report a mild and metal-free method for the chlorination of electron-rich arenes, using nitric acid (NO⁺ source), sodium chloride, and molecular oxygen as the terminal oxidant. The reaction generates hydrogen peroxide as a byproduct and avoids hazardous chlorinating agents. Various arenes were efficiently chlorinated with good yields. Mechanistic studies support a nitrosonium-mediated single-electron pathway involving aryl radicals. The method was applied to the synthesis of pharmaceutical intermediates, including precursors to metoclopramide and oxazepam.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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