可見光催化氨基酸與萘酚進行 C(sp3)-C(sp2) 耦合與三牙基含氮雙烯鈀金屬錯合物在鈴木反應中之研究

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姓名

陳英和(Ying-Ho Chen) 查詢紙本館藏

畢業系所

化學學系

論文名稱

可見光催化氨基酸與萘酚進行 C(sp3)-C(sp2) 耦合與三牙基含氮雙烯鈀金屬錯合物在鈴木反應中之研究
(C(sp3)-C(sp2) Coupling Between Amino Acids and Naphthols by Photoredox Catalysis and Pincer Carbodicarbene Palladium Complex in Suzuki Cross Coupling)

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摘要(中)

摘要
近年來，可見光氧化還原催化劑已被廣泛的應用在有機反應。相較於傳統的加熱反應，光催化可在較為溫和條件進行反應，並且可使用無害的可見光作為能量來源。在本研究中，成功利用可見光催化胺基酸與萘酚進行碳 (sp3)-碳(sp2) 的去羧酸耦合。相較於文獻的結果，此論文所發展的光催化反應可在較溫和的條件下進行，並且對於氨基酸與萘酚的官能基有更大的耐受性。
另外，實驗室先前所合成的的同碳雙碳烯鈀金屬錯合物具有光學性質，意外的也具有光催化反應的效果。在本篇論文中我們探討此錯合物在鈴木反應上的反應性，成功證明其不僅可以進行可見光催化也可以進行有機金屬催化。

摘要(英)

ABSTRACT
Photoredox catalyst has been widely developed to use visible light sources in the organic synthesis recently. A synthetic paradigm using photoredox catalyst has offered many advantages compared to conventional synthetic method based on heating process. For example, the reactions can proceed under mild conditions at ambient temperature. In this thesis work, we have developed a catalytic photoredox reaction for C(sp3)-C(sp2) coupling of naphthols with amino acid through decarboxylative reaction. The coupling reaction was successfully applied to a range of substrates of tertiary amino acids and naphthols under mild condition.
In second part of thesis, we discovered that the pincer carbodicarbene palladium complex has optical properties and acts as photoredox catalyst. We studied the reactivity of pincer carbodicarbene palladium complex in Suzuki- Miyaura cross-coupling reactions. We successfully proved that this catalyst not only served as photocatalyst but also be cross coupling catalyst.

關鍵字(中)

★ 可見光
★ 催化
★ 鈀金屬
★ 同碳雙碳烯
★ 耦合

關鍵字(英)

★ visible light
★ catalysis
★ palladium
★ carbodicarbene
★ coupling

論文目次

目錄
摘要 I
Abstract II
誌謝 III
目錄 V
圖目錄 VII
式目錄 IX
附圖目錄 X
簡稱說明 XII
第一章緒論 1
1-1 可見光氧化還原催化 1
1-2 去羧酸耦合反應 5
1-3 脯氨酸與萘酚的去羧酸耦合反應 9
1-4 含氮雜環碳烯12
1-5 同碳雙碳烯 (carbodicarbene)14
1-6 鈴木反應 (Suzuki coupling) 17
1-7 研究動機18
第二章結果與討論 19
2-1 可見光催化於空氣下將氨基酸與萘酚進行 C(sp3)-C(sp2) 耦合 19
2-2 測試具有光催化性質的含氮雙烯鈀金屬錯合物在鈴木耦合上的反應性 34
第三章結論 37
第四章實驗方法 38
4-1 實驗儀器 38
4-2 藥品與溶劑 39
4-3 合成步驟 40
4-4 Stern-V olmer 螢光淬熄實驗63
參考文獻 64
附錄一核磁共振光譜圖69

參考文獻

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指導教授

王朝諺(Tiow-Gan Ong)

審核日期

2017-7-11

推文