Please use this identifier to cite or link to this item: http://hdl.handle.net/11455/96309
標題: 1.Iodine-Promoted Generation of ortho-Quinone Methide Intermediate and its Application for C-S Bond Cross-Coupling Reaction 2.CuI/Oxalic Diamide-Catalyzed Cross-Coupling of Thiols with Aryl Bromides
1.碘促進鄰甲亞基環己二烯酮的生成及其在碳-硫鍵耦合反應的應用 2.碘化亞銅搭配草醯胺配體催化芳香基溴化物與硫醇之交互耦合反應
作者: Chia-Wei Chen
陳家偉
關鍵字: 鄰甲亞基環己二烯酮
碳-硫鍵
草醯胺配體
交互耦合反應
ortho-Quinone Methide
C-S Bond
Oxalic Diamide
Cross-Coupling
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摘要: In the first part of this thesis, a new and efficient method has been described for generation of o-quinone methides via iodine-induced dehydroxylation of 2-(hydroxymethyl)phenols. The formed reactive o-quinone methide intermediates were trapped by thiols providing stable 2-[(alkyl or arylthio)methyl]phenols under mild conditions. The second part of this thesis, we report a general copper-catalyzed cross-coupling of thiols with aryl bromides by using N-aryl-N'-alkyl oxalic diamide (L3) or N,N'-dialkyl oxalic diamide (L5) as the ligands. Both aryl- and alkyl thiols can be coupled with unactivated aryl bromides to give the desired products in good yields for the first time. Furthermore, this system features broad substrate scope and good tolerance of functional groups. Importantly, the oxalic diamides are stable and can be prepared easily from commercially available cheap starting materials.
本論文中的第一部分,我們開發一個新穎的有效方法,透過碘促進 2-(羥甲基)苯酚進行脫羥基化反應,生成鄰甲亞基環己二烯酮 (o-quinone methides) 中間體。在溫和條件下,形成的反應性鄰甲亞基環己二烯酮中間體,再與烷基或芳香基硫醇反應,生成含有苯酚的穩定硫醚化合物。 在第二部分中,我們利用銅金屬搭配 N-芳基-N'-烷基草醯胺 (L3) 或 N,N'-二烷基草醯胺 (L5) 作為配體,催化芳香基溴化物與硫醇進行交互耦合反應。不論是烷基或芳香基硫醇,都能與活性差的芳香基溴化物反應得到目標產物,且都有優異產率。此外,該反應系統具有對受質應用性廣泛和良好的官能基容忍性。重要的是,草醯胺配體不但穩定也容易從廉價的起始物製備。
URI: http://hdl.handle.net/11455/96309
文章公開時間: 2017-08-08
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