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  • 學位論文

可見光與氧氣致分子內碘環化反應之研究

Visible Light Mediated Aerobic Intramolecular Iodocyclization

指導教授 : 莊敬

摘要


這項研究為通過碘環化作用構建內酯衍生物提供了一種容易獲得的替代催化方法,並允許在C = C上直接激活氧和碘。在這項工作中,我們通過在溫和的條件下使用各種鏈烯酸和2-烯丙基苯酚,報告了可見光介導的功能化內酯的有氧合成。這種方法將為重要的碘內酯的合成提供過渡金屬,光催化劑和無酶途徑。

並列摘要


This study provides an easily accessible alternative catalytic protocol for the construction of lactone derivatives by iodocyclization, and allow the direct activation of oxygen and iodine across the C=C. In this work, we report a visible light-mediated aerobic synthesis of functionalized lactones, by using a variety of alkenoic acids and 2-allyl phenols under mild conditions. This approach will provide a transition metal, photocatalyst, and enzyme-free route to the synthesis of important iodolactones.

參考文獻


1.Kristianslund, R., Tungen, J. E., and Hansen, T. V. Catalytic enantioselective iodolactonization reactions. Organic Biomolecular Chemistry, 2019, 17(12), 3079-3092.
2.Banerjee, K. A., S Laya, M., and V Cabrera, E. Iodocyclization: Past and present examples. Current Organic Chemistry, 2011, 15(7), 1058-1080.
3.Basu, P. K., and Ghosh, A. Regioselective 5-exo-Trig Heterocyclization of 2-Allyl-1-naphthols under the Influence of N-Iodosuccinimide or Molecular Iodine in Aqueous Micelle. Organic Chemistry International, 2012.
4.Danishefsky, S., Schuda, P. F., Kitahara, T., and Etheredge, S. J. The total synthesis of dl-vernolepin and dl-vernomenin. Journal of the American Chemical Society, 1977, 99(18), 6066-6075.
5.Chen, Z., Huang, G., Jiang, H., Huang, H., and Pan, X. Synthesis of 2, 5-disubstituted 3-iodofurans via palladium-catalyzed coupling and iodocyclization of terminal alkynes. The Journal of Organic Chemistry, 2011, 76(4), 1134-1139.

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