研究生: |
王瑩錚 Wang, Ying-Zheng |
---|---|
論文名稱: |
利用有機鏻鹽經由分子內 Wittig 反應合成雙雜環化合物 Synthesis of Bis-heteroarenes Using Phosphonium Salts via Intramolecular Wittig Reactions |
指導教授: |
林文偉
Lin, Wen-Wei |
學位類別: |
碩士 Master |
系所名稱: |
化學系 Department of Chemistry |
論文出版年: | 2017 |
畢業學年度: | 105 |
語文別: | 中文 |
論文頁數: | 420 |
中文關鍵詞: | 威悌反應 、有機鏻鹽 、雙雜環 |
英文關鍵詞: | Wittig reaction, Phosphonium Salts, Bis-heteroarenes |
DOI URL: | https://doi.org/10.6345/NTNU202202815 |
論文種類: | 學術論文 |
相關次數: | 點閱:117 下載:0 |
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第一章、利用新穎的四組成有機鏻鹽高效的合成雙雜環化合物
利用高效的方式生成四組成有機鏻鹽進行分子內 Wittig 反應合成雙雜環化合物,過程無使用金屬試劑,條件溫和,反應中間物穩定易操作,是為傳統偶合反應的替代方案。
第二章、利用聚苯乙烯負載有機磷試劑進行可回收再生之Wittig反應以合成雙雜環化合物
透過固相載體進行反應以簡化純化的步驟及減少試劑的浪費,進而達到環保效益的概念。
Chapter I: Efficient synthesis of bis-heteroarenes using of novel four-components of organic phosphonium salts
An efficient synthetic strategy for bis-heteroarenes has been developed under metal-free conditions. The isolable phosphonium salts obtained via a novel four-component reaction could undergo further acylation and Wittig reaction to produce the bis-heteroarenes. This synthetic strategy can provide an efficient alternative method to the traditional metal-mediated cross-coupling strategies.
Chapter II: Using of polystyrene-bonded organophosphorus reagent for reproducible regeneration of the Wittig reaction to synthesize bis-heteroarenes
A organophosphorus reagent bonded solid supports was used for intramolecular wittig reactions to generate indole-benzofuran cross-coupling type product. This strategy has simplified purification steps, reduce the waste of reagents, phosphine oxide, and achieve the concept of environmental benefits.
(1) Badre, A.; Boulanger, A.; Abou-Mansour, E.; Banaigs, B.; Combaut, G.;
Francisco, C. J. Nat. Prod. 1994, 57, 528.
(2) Molina, P.; Fresneda, P. M.; García-Zafra, S. Tetrahedron Lett. 1995, 36,
3581.
(3) Rey, J. R. C.; Cervino, E. V.; Rentero, M. L.; Crespo, E. C.; Á lvaro, A. O.;
Casillas, M. The Open Orthopaedics Journal 2009, 3, 14.
(4) Nöteberg, D.; Kallin, E.; Wennerstål, M.; Google Patents: 2011.
(5) Vladimirov, Y. A.; Sharov, V. S.; Driomina, E. S.; Reznitchenko, A. V.;
Gashev, S. B. Free Radical Bio. Med. 1995, 18, 739.
(6) Leclerc, M.; Faid, K. Adv. Mater. 1997, 9, 1087.
(7) Ateh, D. D.; Navsaria, H. A.; Vadgama, P. J. Roy. Soc. Interface 2006, 3, 741.
(8) Uygun, A.; Turkoglu, O.; Sen, S.; Ersoy, E.; Yavuz, A. G.; Batir, G. G. Curr.
Appl. Phys. 2009, 9, 866.
(9) Yang, Y.; Lan, J.; You, J. Chem Rev 2017.
(10) Rossi, R.; Lessi, M.; Manzini, C.; Marianetti, G.; Bellina, F. Adv. Synth.
Catal. 2015, 357, 3777.
(11) Seregin, I. V.; Gevorgyan, V. Chem Soc Rev 2007, 36, 1173.
(12) Johansson Seechurn, C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V.
Angew. Chem. Int. Ed. Engl. 2012, 51, 5062.
(13) Kumar, S.; Rathore, V.; Verma, A.; Prasad Ch, D.; Kumar, A.; Yadav, A.;
Jana, S.; Sattar, M.; Meenakshi; Kumar, S. Org. Lett. 2015, 17, 82.
(14) Wirtanen, T.; Mäkelä, M. K.; Sarfraz, J.; Ihalainen, P.; Hietala, S.;
Melchionna, M.; Helaja, J. Adv. Synth. Catal. 2015, 357, 3718.
(15) Zhai, L.; Shukla, R.; Rathore, R. Org. Lett. 2009, 11, 3474.
(16) Marzo, L.; Ghosh, I.; Esteban, F.; König, B. ACS Catal. 2016, 6, 6780.
(17) Raji Reddy, C.; Krishna, G.; Kavitha, N.; Latha, B.; Shin, D.-S. Eur. J. Org.
Chem. 2012, 2012, 5381.
(18) Ji, X.-M.; Zhou, S.-J.; Deng, C.-L.; Chen, F.; Tang, R.-Y. RSC Adv. 2014, 4,
53837.
(19) Cheng, C.; Liu, C.; Gu, Y. Tetrahedron 2015, 71, 8009.
(20) Kraus, G. A.; Guo, H. Org. Lett. 2008, 10, 3061.
(21) Das, U.; Tsai, Y.-L.; Lin, W. Org. Biomol. Chem. 2014, 12, 4044.
(22) Chen, K. W.; Syu, S. E.; Jang, Y. J.; Lin, W. Org. Biomol. Chem. 2011, 9,
2098.
(23) Syu, S.-e.; Lee, Y.-T.; Jang, Y.-J.; Lin, W. Org. Lett. 2011, 13, 2970.
(24) Lee, C.-J.; Jang, Y.-J.; Wu, Z.-Z.; Lin, W. Org. Lett. 2012, 14, 1906.
(25) Louis D. Quin, J. A. T. Fundamentals of Heterocyclic Chemistry: Importance
in Nature and in the Synthesis of Pharmaceuticals citation.
(26) Biaggi, C.; Benaglia, M.; Raimondi, L.; Cozzi, F. Tetrahedron 2006, 62,
12375.
(27) Ganesan, A.; Kothandapani, J.; Subramaniapillai, S. G. RSC Adv. 2016, 6,
20582.
(28) Reddy, M. V.; Chandra Sekhar Reddy, G.; Naidu Kalla, R. M.; Jeong, Y. T.
RSC Adv. 2015, 5, 35267.
(29) Bernard, M.; Ford, W. T. J. Org. Chem. 1983, 48, 326.
(30) Westman, J. Org. Lett. 2001, 3, 3745.
(31) Castells, J.; Font, J.; Virgili, A. J. Chem. Soc. Perk. T. 1 1979, 1.
(32) Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820.
(33) Choi, M. K. W.; He, H. S.; Toy, P. H. J. Org. Chem. 2003, 68, 9831.
(34) Leung, P. S.-W.; Teng, Y.; Toy, P. H. Org. Lett. 2010, 12, 4996.
(35) Roper, K. A.; Berry, M. B.; Ley, S. V. Beilstein. J. Org. Chem. 2013, 9, 1781.
(36) Tang, X.; An, J.; Denton, R. M. Tetrahedron Lett. 2014, 55, 799.
(37) Herault, D.; Nguyen, D. H.; Nuel, D.; Buono, G. Chem Soc Rev 2015, 44,
2508.
(38) Charette, A. B.; Boezio, A. A.; Janes, M. K. Org. Lett. 2000, 2, 3777.
(39) Yang, Y.-C., Doctoral dissertation, Texas A&M University., 2012.
(40) Keglevich, G.; Kégl, T.; Odinets, I. L.; Vinogradova, N. M.; Kollár, L.
Comptes Rendus Chimie 2004, 7, 779.
(41) Imamoto, T.; Kikuchi, S.-i.; Miura, T.; Wada, Y. Org. Lett. 2001, 3, 87.
(42) Chikkali, S. H.; Gudat, D.; Lissner, F.; Nieger, M.; Schleid, T. Dalton Trans
2007, 3906.
(43) Schlindwein, S. H.; Bader, K.; Sibold, C.; Frey, W.; Neugebauer, P.; Orlita,
M.; Slageren, J.; Gudat, D. Inorg. Chem. 2016, 55, 6186.
(44) Rajendran, K. V.; Gilheany, D. G. Chem. Commun. 2012, 48, 817.
(45) Kenny, N. P.; Rajendran, K. V.; Gilheany, D. G. Chem. Commun. 2015, 51,
16561.