Please use this identifier to cite or link to this item: http://hdl.handle.net/11455/14240
標題: 1.通過碳-氫鍵功能化合成芳香基硫醚化合物 2.N-氯代琥珀醯亞胺促進格林納試劑與硫醇之交互耦合反應
1.Synthesis of Aryl Thioethers Through C-H Functionalization 2.NCS-Promoted Cross-Coupling Reaction of Grignard Reagents with Thiols
作者: 鄭濬豪
Cheng, Jun-Hao
關鍵字: 格林納試劑
Grignard Reagents
硫醚
N-氯代琥珀醯亞胺
交互耦合
Thioether
N-chlorosuccinimide
Cross-Coupling
出版社: 化學系所
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摘要: 使用過渡金屬催化交互耦合反應合成重要的化合物已經是被廣泛應用在許多領域。在本論文的第一部分,利用已知的銥金屬做為催化劑使1,3雙取代芳香環上的碳-氫鍵形成碳-硼鍵,再利用氯化亞銅和配體的幫助下,催化碳-硫鍵的生成,得到3,5雙取代硫醚類,這是首次在一鍋化反應中直接生成間位取代硫醚化合物。 本論文的第二部分將介紹新形態的碳-硫鍵生成反應。N-氯代琥珀醯亞胺與硫醇先反應,得到氯硫基的反應中間體,再與格林納試劑進行反應,烷基或芳香基硫醇都有不錯的產率,這也是首次使用N-氯代琥珀醯亞胺將烷基催化硫醇進行碳-硫鍵之生成反應。
Transtion-metal-Catalyzed Cross-Coupling reaction is a powerful strategy for Constracting Carbon-Carbon and Carbon-heteroatom bonds. In the first part of this thesis, the direct meta C-H functionalization of C-H bond of aromatic ring is introduced. The combination of iridium-Catalyzed C-H activation and sequential functionalization of the resulting aryl boronic ester is an excellent approach for regioselection meta C-H functionalization of aromatic C-H bond. The second part of this thesis, although the Grignard reagents have been used as nucleophiles to react with aryl disulfides, leading the corresponding aryl thioethers, these are some drawbacks in these systems. Fisrt, aryl disulfides and thiosulfonates must be prepared in advance. Second, from the atom economic point of view, an equivalent of sulfur moiety will be generated as the byproducts. Thus, it is desirable to develop a convenient method for the synthesis of aryl thioethers through the reaction of Grignard reagents with thiols without the preparation of aryl disulfides. The second of this thesis, the NCS-promoted coupling reaction of Grignard reagents with thiols is reported.
URI: http://hdl.handle.net/11455/14240
其他識別: U0005-3107201211372600
文章連結: http://www.airitilibrary.com/Publication/alDetailedMesh1?DocID=U0005-3107201211372600
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