請用此 Handle URI 來引用此文件：
http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/88126完整後設資料紀錄
| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 邱勝賢 | zh_TW |
| dc.contributor.advisor | Sheng-Hsien Chiu | en |
| dc.contributor.author | 蔡基佑 | zh_TW |
| dc.contributor.author | Chi-You Tsai | en |
| dc.date.accessioned | 2023-08-08T16:24:52Z | - |
| dc.date.available | 2023-11-09 | - |
| dc.date.copyright | 2023-08-08 | - |
| dc.date.issued | 2023 | - |
| dc.date.submitted | 2023-07-17 | - |
| dc.identifier.citation | 1. Stoddart, J. F., Angew. Chem. Int. Ed. 2017, 56, 11094–11125.
2. Coskun, A.; Banaszak, M.; Astumian, R. D.; Stoddart, J. F.; Grzybowski, B. A., Chem. Soc. Rev. 2012, 41, 19–30. 3. (a) Leigh, D. A.; Marcos, V.; Wilson, M. R., ACS Catal. 2014, 4, 4490–4497; (b) Kwan, C.-S.; Chan, A. S. C.; Leung, K. C.-F., Org. Lett. 2016, 18, 976–979; (c) Eichstaedt, K.; Jaramillo-Garcia, J.; Leigh, D. A.; Marcos, V.; Pisano, S.; Singleton, T. A., J. Am. Chem. Soc. 2017, 139, 9376–9381; (d) Dommaschk, M.; Echavarren, J.; Leigh, D. A.; Marcos, V.; Singleton, T. A., Angew. Chem. Int. Ed. 2019, 58, 14955–14958. 4. (a) Ma, X.; Tian, H., Chem. Soc. Rev. 2010, 39, 70–80; (b) Langton, M. J.; Beer, P. D., Acc. Chem. Res. 2014, 47, 1935–1949; (c) Denis, M.; Pancholi, J.; Jobe, K.; Watkinson, M.; Goldup, S. M., Angew. Chem. Int. Ed. 2018, 57, 5310–5314; (d) Lim, J. Y. C.; Marques, I.; Felix, V.; Beer, P. D., Angew. Chem. Int. Ed. 2018, 57, 584–588. 5. (a) Zhao, Y.-L.; Aprahamian, I.; Trabolsi, A.; Erina, N.; Stoddart, J. F., J. Am. Chem. Soc. 2008, 130, 6348–6350; (b) Hsueh, S.-Y.; Kuo, C.-T.; Lu, T.-W.; Lai, C.-C.; Liu, Y.-H.; Hsu, H.-F.; Peng, S.-M.; Chen, C.-H.; Chiu, S.-H., Angew. Chem. Int. Ed. 2010, 49, 9170–9173; (c) Iwaso, K.; Takashima, Y.; Harada, A., Nat. Chem. 2016, 8, 625–632; (d) Goujon, A.; Mariani, G.; Lang, T.; Moulin, E.; Rawiso, M.; Buhler, E.; Giuseppone, N., J. Am. Chem. Soc. 2017, 139, 4923–4928; (e) Tung, S.-T.; Cheng, H.-T.; Inthasot, A.; Hsueh, F.-C.; Gu, T.-J.; Yan, P.-C.; Lai, C.-C.; Chiu, S.-H., Chem. - Eur. J. 2018, 24, 1522–1527. 6. (a) Barat, R.; Legigan, T.; Tranoy-Opalinski, I.; Renoux, B.; Peraudeau, E.; Clarhaut, J.; Poinot, P.; Fernandes, A. E.; Aucagne, V.; Leigh, D. A.; Papot, S., Chem. Sci., 2015, 6, 2608–2613; (b) Gayam, S. R.; Venkatesan, P.; Sung, Y.-M.; Sung, S.-Y.; Hu, S.-H.; Hsu, H.-Y.; Wu, S.-P., Nanoscale, 2016, 8, 12307–12317. 7. Harrison, I. T.; Harrison, S., J. Am. Chem. Soc. 1967, 89, 5723–5724. 8. Schalley, C. A.; Weilandt, T.; Brüggemann, J.; Vögtle, F. Top. Curr. Chem. 2004, 248, 141–200. 9. Asakawa, M.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Bělohradský, M.; Gandolfi, M. T.; Kocian, O.; Prodi, L.; Raymo, F. M.; Stoddart, J. F.; Venturi, M., J. Am. Chem. Soc. 1997, 119, 302–310. 10. Wu, K.-D.; Lin, Y.-H.; Lai, C.-C.; Chiu, S.-H., Org. Lett. 2014, 16, 1068–1071. 11. Chambron, J.-C.; Heitz, V.; Sauvage, J.-P., J. Am. Chem. Soc. 1993, 115, 12378–12384. 12. Nepogodiev, S. A.; Stoddart, J. F., Chem. Rev. 1998, 98, 1959–1976. 13. Xue, M.; Yang, Y.; Chi, X.; Yan, X.; Huang, F., Chem. Rev. 2015, 115, 7398–7501. 14. Chang, Y.-H.; Lee, Y.-J.; Lai, C.-C.; Liu, Y.-H.; Peng, S.-M.; Chiu, S.-H., Org. Lett. 2018, 20, 2416–2419. 15. Hsueh, F.-C.; Tsai, C.-Y.; Lai, C.-C.; Liu, Y.-H.; Peng, S.-M.; Chiu, S.-H., Chem. Commun. 2020, 56, 4773–4776. 16. Chiang, T.-H.; Tsou, C.-Y.; Chang, Y.-H.; Lai, C.-C.; Cheng, R. P.; Chiu, S.-H., Org. Lett. 2021, 23, 5787–5792. 17. Herrmann, W. A.; Köcher, C., Angew. Chem. Int. Ed. 1997, 36, 2162–2187. 18. Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F., Nature 2014, 510, 485–496. 19. Nahra, F.; Gómez-Herrera, A.; Cazin, C. S. J., Dalton Trans. 2017, 46, 628–631. 20. (a) Egbert, J. D.; Cazin, C. S. J.; Nolan, S. P., Catal. Sci. Technol. 2013, 3, 912–916; (b) Lazreg, F.; Nahra, F.; Cazin, C. S. J., Coord. Chem. Rev. 2015, 293-294, 48–79. 21. Arduengo, A. J.; Dias, H. V. R.; Calabrese, J. C.; Davidson, F., Organometallics 1993, 12, 3405–3409. 22. Raubenheimer, H. G.; Cronje, S.; Olivier, P. J.; Toerien, J. G.; van Rooyen, P. H., Angew. Chem. Int. Ed. 1994, 33, 672–673. 23. Fraser, P. K.; Woodward, S., Tetrahedron Lett. 2001, 42, 2747–2749. 24. Jurkauskas, V.; Sadighi, J. P.; Buchwald, S. L., Org. Lett. 2003, 5, 2417–2420. 25. Díez-González, S.; Nolan, S. P., Acc. Chem. Res. 2008, 41, 349–358. 26. Van Veldhuizen, J. J.; Campbell, J. E.; Giudici, R. E.; Hoveyda, A. H., J. Am. Chem. Soc. 2005, 127, 6877–6882. 27. Boogaerts, I. I. F.; Fortman, G. C.; Furst, M. R. L.; Cazin, C. S. J.; Nolan, S. P., Angew. Chem. Int. Ed. 2010, 49, 8674–8677. 28. Biffis, A.; Tubaro, C.; Scattolin, E.; Basato, M.; Papini, G.; Santini, C.; Alvarez, E.; Conejero, S., Dalton Trans. 2009, 7223–7229. 29. Tubaro, C.; Biffis, A.; Scattolin, E.; Basato, M., Tetrahedron 2008, 64, 4187–4195. 30. Lebel, H.; Davi, M.; Díez-González, S.; Nolan, S. P., J. Org. Chem. 2007, 72, 144–149. 31. Díez-González, S.; Nolan, S. P., Angew. Chem. Int. Ed. 2008, 47, 8881–8884. 32. Kolb, H. C.; Finn, M. G.; Sharpless, K. B., Angew. Chem. Int. Ed. 2001, 40, 2004–2021. 33. Meldal, M.; Tornøe, C. W., Chem. Rev. 2008, 108, 2952–3015. 34. Bodine, K. D.; Gin, D. Y.; Gin, M. S., J. Am. Chem. Soc. 2004, 126, 1638–1639. 35. Ramsubhag, R. R.; Dudley, G. B., Org. Biomol. Chem. 2016, 14, 5028–5031. 36. Sletten, E. M.; Bertozzi, C. R., Angew. Chem. Int. Ed. 2009, 48, 6974–6998. 37. Mamidyala, S. K.; Finn, M. G., Chem. Soc. Rev. 2010, 39, 1252–1261. 38. Thirumurugan, P.; Matosiuk, D.; Jozwiak, K., Chem. Rev. 2013, 113, 4905–4979. 39. Breugst, M.; Reissig, H.-U., Angew. Chem. Int. Ed. 2020, 59, 12293–12307. 40. Aucagne, V.; Leigh, D. A., Org. Lett. 2006, 8, 4505–4507. 41. Elamari, H.; Meganem, F.; Herscovici, J.; Girard, C., Tetrahedron Lett. 2011, 52, 658–660. 42. Beal, D. M.; Albrow, V. E.; Burslem, G.; Hitchen, L.; Fernandes, C.; Lapthorn, C.; Roberts, L. R.; Selby, M. D.; Jones, L. H., Org. Biomol. Chem. 2012, 10, 548–554. 43. Arumugam, S.; Popik, V. V., J. Org. Chem. 2014, 79, 2702–2708. 44. Hatit, M. Z. C.; Sadler, J. C.; McLean, L. A.; Whitehurst, B. C.; Seath, C. P.; Humphreys, L. D.; Young, R. J.; Watson, A. J. B.; Burley, G. A., Org. Lett. 2016, 18, 1694–1697. 45. Yuan, Z.; Kuang, G.-C.; Clark, R. J.; Zhu, L., Org. Lett. 2012, 14, 2590–2593. | - |
| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/88126 | - |
| dc.description.abstract | 我們合成了具有車輪烷結構的NHC-CuI 錯合物，並使其作為立體選擇性的催化劑，來進行銅催化的疊氮化物/炔烴環加成，完成一鍋化的順序連接化學反應。利用套在車輪烷上的大環分子，能讓金屬錯合物選擇性地對體積較小的疊氮化物/炔進行催化。之後通過照光，可以將具有光解基團的大環分子從車輪烷上移去，使啞鈴分子上的NHC-CuI金屬催化中心催化體積較大的疊氮化物/炔，進行點擊反應。透過這樣的策略，我們可以在單個密封瓶中使兩種不同的疊氮化物選擇性地和雙炔分子反應，生成主要的雙三唑產物 (84%)。 | zh_TW |
| dc.description.abstract | We synthesize NHC-CuI complexes with rotaxane architecture, using them as sterically sensitive catalysts for one-pot sequential ligation by copper-catalyzed azide/alkyne cycloadditions. Photolabile and sterically encumbered complexes first catalyze the ligation of less bulky azide/alkyne pairs. Through irradiation with light, the protective macrocyclic components can be removed from the rotaxane structure, and the resulting dumbbell components with NHC-CuI complexes catalyze the second click reaction of bulkier azide/alkyne pairs. Using this approach, we can predominantly obtain a bis-triazole product (84%) from a mixture of two sterically distinct azides and a diyne in a single sealed pot. | en |
| dc.description.provenance | Submitted by admin ntu (admin@lib.ntu.edu.tw) on 2023-08-08T16:24:52Z No. of bitstreams: 0 | en |
| dc.description.provenance | Made available in DSpace on 2023-08-08T16:24:52Z (GMT). No. of bitstreams: 0 | en |
| dc.description.tableofcontents | 口試委員審定書 i
中文摘要 ii 英文摘要 iii 論文發表 iv 目錄 v 圖目錄 vi 第一章 導論 1 1.1 車輪烷 1 1.2 車輪烷的合成 2 1.3 銅金屬氮異環碳烯錯合物(N-heterocyclic carbene copper complex) 6 1.4 點擊化學（click chemistry） 9 第二章 結果與討論 11 2.1 研究動機 11 2.2 合成具有銅金屬氮異環碳烯錯合物的車輪烷 16 2.3 選擇性測試 20 2.4 一鍋化合成 27 2.5 結論 30 第三章 實驗部份 31 第四章 參考文獻 45 第五章 附錄 49 | - |
| dc.language.iso | zh_TW | - |
| dc.subject | 順序連接化學反應 | zh_TW |
| dc.subject | 車輪烷 | zh_TW |
| dc.subject | 氮異環碳烯 | zh_TW |
| dc.subject | Sequential Click Ligations | en |
| dc.subject | Rotaxanes | en |
| dc.subject | N-Heterocyclic Carbene | en |
| dc.title | 以銅金屬氮異環碳烯車輪烷完成一鍋化的順序連接化學反應 | zh_TW |
| dc.title | N-Heterocyclic Carbene Copper(I) Rotaxanes Mediate Sequential Click Ligations with All Reagents Premixed | en |
| dc.type | Thesis | - |
| dc.date.schoolyear | 111-2 | - |
| dc.description.degree | 博士 | - |
| dc.contributor.oralexamcommittee | 陳平;徐秀福;李文山;何佳安 | zh_TW |
| dc.contributor.oralexamcommittee | Richard Ping Cheng;Hsiu-Fu Hsu;Wen-Shan Li;Ja-an Annie Ho | en |
| dc.subject.keyword | 車輪烷,氮異環碳烯,順序連接化學反應, | zh_TW |
| dc.subject.keyword | Rotaxanes,N-Heterocyclic Carbene,Sequential Click Ligations, | en |
| dc.relation.page | 85 | - |
| dc.identifier.doi | 10.6342/NTU202301640 | - |
| dc.rights.note | 同意授權(全球公開) | - |
| dc.date.accepted | 2023-07-17 | - |
| dc.contributor.author-college | 理學院 | - |
| dc.contributor.author-dept | 化學系 | - |
| 顯示於系所單位： | 化學系 | |
文件中的檔案：
| 檔案 | 大小 | 格式 | |
|---|---|---|---|
| ntu-111-2.pdf | 16.88 MB | Adobe PDF | 檢視/開啟 |
系統中的文件，除了特別指名其著作權條款之外，均受到著作權保護，並且保留所有的權利。