- 學位論文
芳香雜環碘化物之水相自身耦合反應：有機光電材料重要前驅物之綠色化學合成法之研究
Green Synthesis of Organic-Electronics-Oriented Precursors via On-Water and Under-Air Homocoupling of (Hetero)aryl Iodides
摘要
我們報導了以綠色化學方式合成自身耦合產物，其單元為重要的有機光電小分子材料。合成不同種類的聯噻吩衍生物與具官能基的芳香環，其中最環保的是使用水作為溶劑且異質催化劑Pd/C可回收再使用。 我們發現使用催化劑Pd/C較Pd(OAc)2反應性好，當使用Pd(OAc)2催化芳香雜環碘化物時，會形成許多副產物包含還原產物與寡聚物，以致於主要反應的產率較低。研究中找到之最佳化條件亦適用於芳香(雜)環，在此反應條件中，具有好的官能基容忍性，可容忍如酯基、酮基、醛基、腈基、硝基、鹵素基等等。 目前自身耦合產物從未以綠色化學方法合成含噻吩小分子之有機光電材料，我們期望可以藉由更環保的方法合成具有功能性之建構單元。
並列摘要
We report herein an operationally simple homocoupling reaction that targets on the green synthesis of organic-electronically important building blocks. A variety of synthetically useful bithiophene derivatives and functionalized biphenyls are efficiently prepared by a on-water and under-air protocol using recyclable Pd/C as catalyst. We find that Pd/C gives generally higher and cleaner homocoupling conversions than using Pd(OAc)2 in the cases of (hetero)aryl iodides since Pd(OAc)2 triggers more side reactions including dehalogenations and oligomerizations. Under the optimum conditions, a broad range of functional groups such as ester, ketone, aldehyde, nitrile, nitro group, chloride, and bromide are well tolerated. We expect present methodology would make a valuable synthetic contribution towards bridging green chemistry with thiophene-based organic materials.
參考文獻
延伸閱讀
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