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  • 學位論文

以水做為溶劑並使用碘離子與氧氣進行可見光催化之環化之研究

Visible light induced iodocyclization using iodide and molecular oxygen in aqueous solution

指導教授 : 莊敬
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摘要


本論文透過可見光催化、氧氣與醋酸的條件下,利用碘離子進行碘內酯反應建構出內酯(lactone)及異色滿酮(isochromanone)衍生物,另外也進行碘環化反應建立出苯并呋喃(benzofuran)衍生物。在實驗中以水做為主要的反應溶劑,降低了有機溶劑所佔的比例,以碘化鉀做為碘離子的提供來源,取代了普遍會使用的碘。本論文也嘗試將碘鹽取代碘,利用碘離子與可見光催化替代碘分子與有機溶劑進行多樣性反應。

並列摘要


In this thesis, under the conditions of visible-light catalysis, oxygen and acetic acid, iodide ions were used to react iodolactonization to construct lactone and isochromanone derivatives, and also carried out iodocyclization to construct benzofuran derivatives. In the experiment, water was used as the main reaction solvent to reduce the proportion of organic solvents, and potassium iodide was used as the source of iodide ions to replace the commonly used iodine. This thesis also tries to replace iodine with iodine salt, and use iodide ions and visible-light catalysis instead of iodine molecules and organic solvents for diverse reactions.

參考文獻


(1) Verma, A.; Aggarwal, T.; Kumar, S.; K. Iodine-Mediated Synthesis of Heterocycles: Via Electrophilic Cyclization of Alkynes. J. Name., 2013, 00, 1-3.
(2) Kitagawa, O.; Hanano, T.; Tanabe, K.; Shiro, M.; Taguchi, T., Enantioselective Halocyclization Reaction Using a Chiral Titanium Complex. J. Chem. Soc., Chem. Commun., 1992, 14, 1005-1007.
(3) Leonard, K. A.; Zhou, F.; Detty, M. R. Chalcogen(IV)-Chalcogen(II) Redox Cycles. 1. Halogenation of Organic Substrates with Dihaloselenium(IV) and-Tellurium(IV) Derivatives. Dehalogenation of Vicinal Dibromides with Diaryl Tellurides. Organometallics 1996, 15, 4285-4292.
(4) Liu, Y.; Wang, B.; Qiao, X.; Tung, C.-H.; Wang, Y., Iodine/Visible Light Photocatalysis For Activation of Alkynes for Electrophilic Cyclization Reactions. ACS Catal., 2017, 7, 4093-4099.
(5) Olmsted III, J.; Karal, G., Iodine-sensitized Photoformation of Singlet Oxygen. J. Am. Chem. Soc., 1972, 10, 3305–3310.

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