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    Title: 鎳族金屬錯合物催化晴基的插入反應以及其在有機合成上之應用
    Other Titles: Nickel Group Catalyzed 1,2-Insertion of Nitrile and the Application to Construct Heterocyclic Compounds
    Authors: 謝仁傑
    Contributors: 淡江大學化學學系
    Date: 2011
    Issue Date: 2012-05-02 09:51:02 (UTC+8)
    Abstract: 【重提計畫-鎳族金屬錯合物催化晴基的插入反應以及其在有機合成上之應用】 近幾年隨著化學的發展,有機金屬催化有機合成反應日趨重要。以往必須以較多且較 困難的步驟所建構的分子,如今只需要以簡單的有機金屬催化反應即達成。因此有機 金屬錯合物催化有機合成反應的研究幾年來成為有機與無機化學研究的重點,不但吸 引相當多的化學家投入,也嚴然成為非常熱門與龐大的領域。此計劃內容便是以研究 鎳族金屬錯合物催化晴基插入反應來探索更多建構有機化合物合成的新方法,以下分 為三個主題介紹: (1) 鎳族過渡金屬催化SP2 碳-鹵化合物對晴基的插入反應: 根據文獻報導,晴基的插入反應在大部分的情況下只有鋰金屬與鎂金屬能夠有效 地完成。過度金屬錯合物在晴基插入反應的應用上極少被報導,許多過渡金屬錯合物 雖然能對晴基進行插入反應,卻會形成穩定的金屬錯合物而降低其在有機合成上的應 用性。我們的目的是完成鎳族金屬錯合物催化一系列SP2 碳鹵鍵對晴基進行插入反應, 而第一階段的目標則是希望可以完成偶合反應,同時探討此類反應未來的應用性。 (2) 鎳族過渡金屬催化晴基插入反應在合成多環化合上之應用: 在偶合反應成功後我們將嘗試利用一系列反應的組合來建構含氮類的多環雜環化 合物,例如Isoindole、Isoindol-1-one、Oxindole 以及lactone 等雜環化合物。其中Oxindole 等化合物具有天然物骨架,因此有機會進一步在天然物的合成上進行應用。 (3) 鎳族過渡金屬催化N-H 鍵對晴基的插入反應以及在偶合與環化反應之應用: 在完成鎳族金屬錯合物催化SP2 碳鹵鍵對晴基進行插入反應後,我們會試著將反應 延伸至N-H 鍵的活化以及其對晴基進行插入反應的應用。若此類反應能順利完成,便 可大幅度的增加其在有機合成反應上的應用性。
    【Re-proposed proposal-Nickel group catalyzed 1,2-insertion of nitrile and the application to construct heterocyclic compounds】 In recent years, the transition metal catalytic reaction has attracted considerable attention, the importance of this field become higher and higher. In this proposal, we will describe the research plan in our group for the coming three years which involves the novel organometallic catalytic reaction and establishing the skeleton of natural products. A variety of new reactions catalyzed by nickel group complexes and application for some of these reactions are proposed. The important reactions that will be investigated are divided into three parts and summarized below. (1) Nickel Group Complexes Catalyzed Insertion of SP2 Carbon-Halide bond to Nitrile: According to the reports, CN insertion was generally well achieved by the lithium and Grignard reagents. Although some cases were carried out by transition metal complexes, most of them could be done but still coordinate to central metal as emine ligands in the complex. In this proposal we wish to achieve the CN insertion of SP2 C-X bond via the nickel group complex and applied it into the organic synthesis. (2) Construction of Poly-heterocyclic Compounds via the Nickel Catalyzed Tandem CN Insertion with Associated Reactions: Once we achieved the nickel catalyzed CN insertion of SP2 C-X bond, we will extend the application into the construction of poly-heterocyclic compounds. The tandem CN insertion with other associated reactions could provide series heterocyclic compounds such as isoindole, oxisoindole, oxindole and lactone etc. The heterocyclic compounds which relative to the core structures of natural products could be further established and applied to the total synthesis. (3) Nickel Group Complexes Catalyzed Insertion of N-H bond to Nitrile as well as the Application in Organic Synthesis: After finishing the application of CN insertion of C-X bond to form the heterocyclic compounds, we will try to exam the possibility of insertion of N-H (or O-H) bond to CN. Thus, we could widely establish various functional groups and heterocyclic compounds by insertion of different moiety to CN.
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