銅金屬催化碳-氧偶合反應路徑

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姓名

陳弘杰(Hong-Jie Chen) 查詢紙本館藏

畢業系所

化學學系

論文名稱

銅金屬催化碳-氧偶合反應路徑
(Mechanism of Copper complexes as catalysts for C-O coupling reactions)

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至系統瀏覽論文 ( 永不開放)

摘要(中)

碳-氧偶合反應在天然物和材料的合成方面有很好的應用性，因
此科學家在近幾十年發表了無數篇的文獻。
在本篇論文我們利用銅當作催化反應的過渡金屬分別在四個不
同條件下進行反應，分別為CuI/phen/K2CO3, CuI/K2CO3, CuI/phen/Cs2CO3, CuI/Cs2CO3。接著我們希望能找出催化反應的中間物進而確認反應路徑，因此實驗室選擇使用ESI-MS 進行測量，最後再比較4-bromotoluene 和2-bromotoluene 選擇率確認我們測量出的結構是否符合。
我們發現大部分科學家所推測的(phen)Cu(OR)中間物並不一定都是屬於主要反應路徑的起始結構。

摘要(英)

C-O coupling reactions are widely used in natural products and materials synthesis, thus, in recent decades, scientists have reported numerous articles.
In this article, we used copper as the transition metal to do catalytic reactions were carried out in four conditions which were CuI/phen/K2CO3, CuI/K2CO3, CuI/phen/Cs2CO3, CuI/Cs2CO3. After that we hope to find the intermediate of catalytic reactions and then confirm the reaction paths,
thus, our lab choose to use the ESI-MS. Finally, comparing the selectivity of 4-bromotoluene and 2-bromotoluene confirmed the structures we measured by ESI-MS.
We found that most scientists speculated the intermediate (phen)Cu(OR) doesn’t necessarily belong to the main catalytic reaction paths as starting structure.

關鍵字(中)

★ 碳-氧偶合反應

關鍵字(英)

★ C-O coupling reaction

論文目次

目錄
謝誌................................................................................................. I
中文摘要........................................................................................II
Abstract ....................................................................................... III
目錄.............................................................................................. IV
表目錄.......................................................................................... VI
圖目錄.........................................................................................VII
第一章緒論.................................................................................1
1-1 偶合反應的簡介與機制.................................................1
1-2 銅金屬偶合催化反應的簡介.........................................5
1-3 研究動機.......................................................................10
第二章實驗...............................................................................14
2-1 實驗藥品........................................................................14
2-1.1 溶劑......................................................................14
2-1.2 藥品......................................................................15
2-1.3 氣體......................................................................15
2-2 實驗儀器........................................................................16
2-2.1 手套箱（Glove Box）..........................................16
2-2.2 氣相層析儀(GC)...................................................16
2-2.3 電灑法飛行式質譜儀 (ESI-TOF) ....................... 16
2-3 CuI 在不同環境下進行碳-氧偶合反應(C-O coupling
reaction .......................................................................................... 17
2-4 CuI 在不同環境下對4-Bromotoluene 和2-Bromotoluene
做碳-氧鍵偶合反應(C-O coupling reactions)選擇率....................18
第三章結果與討論....................................................................19
3-1 CuI / 1,10-phenanthrolin 或CuI 與不同的鹼進行碳-氧鍵
偶合反應(C-O coupling reactions) ................................................19
3-2 利用ESI-MS 進行碳-氧鍵偶合反應(C-O coupling
reactions)中間物的檢測................................................................ 22
3-3 CuI / 1,10-phenanthrolin 或CuI 與不同的鹼進行碳-氧鍵
偶合反應(C-O coupling reactions)比較2-bromotoluene 和
4-bromotoluene 的選擇性.............................................................. 30
第四章結論...............................................................................33
參考資料.......................................................................................34
附錄一........................................................................................... 37
附錄二........................................................................................... 43
附錄三........................................................................................... 55

參考文獻

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指導教授

徐新光(Shin-Guang Shyu)

審核日期

2011-7-20

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