無鈀催化劑參與反應的雙芳香族化合物合成方法

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Title:	無鈀催化劑參與反應的雙芳香族化合物合成方法
Other Titles:	Synthesis of biaryls without the presence of palladium catalyst
Authors:	蔡亨澤;Tsai, Heng-tser
Contributors:	淡江大學化學學系碩士班李世元;Lee, Adam Shih-yuan
Keywords:	自身耦合反應;雙芳香族化合物;Self-coupling Reaction;Biaryls;Palladium;Barbier-type Reaction;Iron Trichloride
Date:	2009
Issue Date:	2010-01-11 02:44:00 (UTC+8)
Abstract:	雙芳香族化合物 (Biaryls) 在有機合成反應中扮演著重要角色，常見製備雙芳香族化合物的方法是使用價錢昂貴的鈀（Pd）、具毒性的鎳 (Ni) 或需高溫反應的銅 (Cu) 等過渡金屬元素進行催化反應。本實驗室成功發展以三氯化鐵 (FeCl3) 為催化劑的巴比艾爾形式反應 (Barbier-type Reaction) 進行雙芳香族化合物的合成。將芳香族鹵化物 (Aryl Halides)、未活化的金屬鎂 (Mg)、三氯化鐵催化劑，在四氫呋喃 (THF) 為溶劑下進行加熱迴流反應，可生成雙芳香族化合物。對於金屬鎂的活化，本研究分別利用1,2-二溴乙烷 (BrCH2CH2Br) 及碘 / 三乙基胺 (I2 / Et3N) 兩種不同方式進行活化性質研究。此種一鍋式 (One-Pot) 反應純化步驟簡單，且三氯化鐵催化劑價格遠比其他過渡金屬催化劑便宜許多，此反應形式具潛力在工業應用量產雙芳香族化合物。 Biaryl compounds play important roles in organic synthesis, they usually are prepared by transition metal catalyzed coupling reactions. Our laboratory has developed a novel synthetic strategy without the introduction of palladium to synthesize biaryl compounds. High yield of biaryl compound was obtained from the reaction of aryl halide, magnesium powder, and iron trichloride (FeCl3) as catalyst in THF via Barbier-type reaction condition. Two different methods of magnesium activation process were also discussed under the reaction condition. The use of iron trichloride is much more cheaper than other transition metal catalyst, and this reaction method can be applied to a large-scale manufacturing procedure for synthesis of biaryls.
Appears in Collections:	[Graduate Institute & Department of Chemistry] Thesis

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