跳到主要內容

臺灣博碩士論文加值系統

(3.236.110.106) 您好!臺灣時間:2021/07/26 00:40
字體大小: 字級放大   字級縮小   預設字形  
回查詢結果 :::

詳目顯示

: 
twitterline
研究生:黃俊銘
研究生(外文):Chun-Min Haung
論文名稱:以鐵三價在水中催化芳基碘與具有活性的烯類進行共軛加成
論文名稱(外文):FeCl3-Catalyzed Conjugate Addition of Aryl Iodides with Activated Olefins in Aqueous Phase
指導教授:蔡福裕
指導教授(外文):Fu-Yu Tsai
口試委員:王朝諺吳學亮
口試委員(外文):Tiow-Gan OngHsyueh-Liang Wu
口試日期:2012-07-17
學位類別:碩士
校院名稱:國立臺北科技大學
系所名稱:有機高分子研究所
學門:工程學門
學類:化學工程學類
論文種類:學術論文
論文出版年:2012
畢業學年度:100
語文別:中文
論文頁數:111
中文關鍵詞:鐵三價催化系統綠色化學
外文關鍵詞:FeCl3•6H2O/cationic 22’-bipyridineWaterGreen Chemistry
相關次數:
  • 被引用被引用:0
  • 點閱點閱:106
  • 評分評分:
  • 下載下載:1
  • 收藏至我的研究室書目清單書目收藏:0
我們利用鐵三價/2,2’-雙吡啶催化系統在水中將芳基碘與具有活性的烯類進行合成,其中以鋅作為還原劑,KOAc為鹼,溫度80℃下反應12個小時,可以得到 Michael-type的加成產物,且具有相當不錯的產率。此一催化系統非常適合用來活化芳基碘去進行反應,且此反應具有兩項優勢:其一,在所有的B族過渡金屬中,鐵是最便宜的過渡金屬,可以節省成本,另外我們使用地球含量最多、對環境汙染最少、最環保的溶劑,水做為此反應的主要溶劑,使此反應符合綠色化學的規範,藉此大大提升此反應的可行性。

An efficient FeCl3•6H2O/cationic 2,2’-bipyridine system catalyzed cross-coupling of aryl iodides with activated olefins in water in the presence of Zn as the reductant, giving Michael-type addition products in good to high yields. The present system provides an extremely suitable catalyst for the activation of a variety of aryl iodides and it has two advantages: iron is the cheapest transition-metal, less environmental pollution and the greenest solvent, water, is employed as the reaction medium.

目錄

中文摘要 Ⅰ
英文摘要 Ⅱ
誌謝 Ⅲ
目錄 Ⅳ
表目錄 Ⅵ
圖目錄 Ⅶ
第一章 緒論 1
1.1 前言 1
1.2 綠色化學 2
1.3 過渡金屬催化反應 5
1.3.1 C-C bond formation之簡介 5
1.4 C-C鍵生成相關反應之研究 6
1.4.1 常見的偶合反應之簡介 6
1.4.2 Conjugate addition之相關研究 9
1.4.2.1 Copper-catalyzed reaction 9
1.4.2.2 Palladium-catalyzed reaction 14
1.4.2.3 Other transition metal catalyzed reaction 32
1.5 研究目的與動機 41
第二章 實驗部分 43
2.1 實驗儀器 43
2.1.1 氣相層析儀 43
2.1.2 核磁共振光譜儀 43
2.2 實驗藥品 44
2.3 實驗過程 44
2.4 實驗步驟與光譜數據 45
2.4.1 Cationic 2,2’-bipyridyl ligand合成與光譜 45
2.4.2 鐵觸媒催化 Aryl iodides及 activated olefins進 conjugated addition實驗步驟與光譜數據 49
2.4.3 水溶性鐵觸媒之再使用反應流程 51
第三章 實驗結果與討論 70
3.1 利用鐵觸媒催化 Aryl iodides及 activated olefins進行conjugated addition之結果與討論 70
3.1.1 conjugated addition的最適化反應條件探討 70
3.1.2 鐵觸媒催化 aryl iodidy與 butyl acrylate之結果與討論 73
3.1.3 鐵觸媒催化 aryl iodidy與 tert-butyl acrylate之結果與討論 77
3.1.4 鐵觸媒催化 aryl iodidy與 styrene之結果與討論 80
3.1.5 鐵觸媒催化 aryl iodidy與 2-cyclohexenone之結果與討論 83
3.1.6 鐵觸媒催化 β–Hydrogen的 CSP3–I與 activated olefins之結果與討論 86
3.1.7 鐵觸媒催化 aryl iodidy與 trans-4-phenyl-3-buten-2-one或是 trans-cinnamaldehyde之結果與討論 88
3.2 鐵觸媒催化 Aryl Iodides與 Activated Olefins推測之反應機制 89
3.3 水溶性鐵觸媒之再回收使用活性測試 92
3.3.1 鐵觸媒催化 aryl iodidy與 butyl acrylate之再回收使用結果與討論 92
第四章 結論 94
參考文獻 95
附錄 99


參考文獻

[1] 綠色化學理論與應用; P. C. Anastas, J. C. Warner編著;李朝軍、王東譯;科學出版社;2002年。
[2] 陳永祥、張裕昌、李雲嫦、趙弈姼;科學發展;2005;396;56-61。
[3] P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992.
[4] Gareth P. Howell. Organic Process Research and Development Review. December 22, 2011.
[5] B. H. Lipshutz, R.S. Wilhelm, J. A. Kozlowski, J. Org. Chem. 1984, 49, 3938-3942.
[6] P. Knochel, M. C.P. Yeh, S. C. Berk, J. Talbert, J. Org. Chem. 1988, 53, 2390.
[7] M. C. P. Yeh, P. Knochel, W. M.Butler, S. C. Berk, Tetrahedron Lett. 1988, 29, 3053.
[8] Y. Tamaru, H. Tanigawa, T. Yamamoto, Z. Yoshida, Angew. Chem. 1989, 101, 358.
[9] I. Klement, H.Stadtmuller, P. Knochel, Tetrahedron Lett. 1997, 38, 1927-1930.
[10] G. Varchi, A. Ricci, G. Cahiez, P. Knochel, Tetrahedron 2000, 56, 2727-2731.
[11] C. S. Cho, S. Motofusa, K. Ohe, S. Uemura, S. C. Shim, J. Org. Chem. 1995, 60, 883.
[12] S. E. Denmark, N. Amishiro, J. Org. Chem. 2003, 68, 6997-7003.
[13] T. Nishikata, Y. Yamamoto, N. Miyaura, Angew. Chem. Int. Ed. 2003, 42, 2768.
[14] T. Nishikata, Y. Yamamoto, N. Miyaura, Tetrahedron Lett. 2007, 48, 4007.
[15] T. Nishikata, Y. Yamamoto, N. Miyaura, Adv. Synth. Catal. 2007, 349, 1759.
[16] F. Gini, B. Hessen, A. J. Minnaard, Org. Lett. 2005, 7, 5309.
[17] X Lu, S. Lin, J. Org. Chem. 2005, 70, 9651.
[18] S. Lin, X. Lu, Tetrahedron Lett. 2006, 47, 7167.
[19] T. Zhang, M. Shi, Chem. Eur. J. 2008, 14, 3759.
[20] S. E. Denmark, N. Amishiro, J. Org. Chem. 2003, 68, 6997.
[21] T. Nishikata, Y. Yamamoto, N. Miyaura, Chem. Lett. 2003, 32, 752.
[22] T. Nishikata, Y. Yamamoto, I. D. Gridnev, N. Miyaura, Organometallics. 2005, 24, 5025.
[23] R. Lerebours, C. Wolf, Org. Lett. 2007, 9, 2737.
[24] T. Ohe, S. Uemura, Tetrahedron Lett. 2002, 43, 1269.
[25] T. Nishikata, Y. Yamamoto, N. Miyaura, Chem. Lett. 2005, 34, 720.
[26] H. Horiguchi, H. Tsurugi, T. Satoh, M. Miura, J. Org. Chem. 2008, 73, 1590-1592.
[27] S. –H. Huang, T. –M. Wu, F. –Y. Tsai, Appl. Organometal. Chem. 2010, 24, 619-624.
[28] A. L. Gottumukkala, J. G. de Vries, A. J. Minnaard, Chem. Eur. J. 2011, 17, 3091 – 3095.
[29] R. Sustmann, P. Hopp, P. Holl, Tetrahedron Lett. 1989, 375, 259.
[30] J. Westermann, U. Imbery, A. T. Nguyen, K. Nickisch, Eur. J. Inorg. Chem. 1998, 295-298.
[31] S. Condon, J. Y. Nedelec, Synthesis. 2004, 18, 3070-3078.
[32] P .–S. Lin, M. Jeganmohan, C. –H. Cheng, Chem. Asian J. 2007, 2, 1409 – 1416.
[33] T. Miura, M. Murakami, Chem. Commun. 2005, 5676-5677.
[34] M. L. Kantam, V. B. Subrahmanyam, K. B. S. Kumar, G. T.Venkanna, B. Sreedhar, Helvetica Chimica Acta. 2008, 91, 1947–1953.
[35] N. Kuuloja, M. Vaismaa, R. Franzen , Tetrahedron. 2012, 68, 2313 –2318.
[36] P. Gomes, C. Gosmini, J. Y. Nedelec, J. Perichon, Tetrahedron Lett. 2000. 3385-3388.
[37] P. Shukla, Y. –C. Hsu, C. – H. Cheng, J. Org. Chem. 2006, 71, 655-658.
[38] M. Amatore, C. Gosmini, J. Perichon, J. Org. Chem. 2006, 71, 6130-6134.
[39] M. Amatore, C. Gosmini, Synlett. 2009, 7, 1073-1076.
[40] T. Mizoroki, K. Mori, A. Ozaki, Bull. Chem. Soc. Jpn. 1971, 44, 581.
[41] R. F. Heck, J. P. Nolley, Jr., J. Am. Chem. 1972, 37, 2320.
[42] D. Milstein, J. K. Stille, J. Am. Chem. Soc. 1978, 100, 3636.
[43] N. Miyaura, K. Yamada, A. Suzuki, Tetrahedron Lett. 1979, 20, 3437.
[44] L. Cassar, J. Organomet. Chem. 1975, 93, 253.
[45] H. A. Dieck, F. R. Heck, J. Organomet. Chem. 1975, 93, 259.
[46] K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467.
[47] E. Negishi, A. O. King, N. Okukado, J. Org. Chem. 1977, 42, 1821.
[48] S. –H. Huang, T. –M. Wu, F. –Y. Tsai, Appl. Organometal. Chem. 2010, 24, 619-624.
[49] S. –H. Huang, G.-J. Chen, F. –Y. Tsai, Molecules. 2010, 15, 315-330.
[50] W. –Y. Wu, S. –N. Chen, F. –Y. Tsai, Tetrahedron Lett. 2006, 47, 9267.
[51] Y. –H. Wang, F.-Y. Tsai, Chem. Lett. 2007, 36, 1492.
[52] S. –N. Chen, W. –Y. Wu, F. –Y. Tsai, Tetrahedron. 2008, 64, 8164.
[53] S. –N. Chen, W. –Y. Wu, F. –Y. Tsai, Green Chem. 2009, 11, 269.
[54] S. –N. Chen, W. –Y. Wu, F. –Y. Tsai, Green Chem. 2009, 11, 326.
[55] A. R. Oki, R. J. Morgan, Synth. Commun. 1995, 25, 4093.
[56] G. Will, G. Boschloo, S. N. Rao, D. Fitzmaurice, J. Phys. Chem. B. 1999, 103, 8067-8079.
[57] P. S. Herradura, K. A. Pendola, R. K. Guy, Org. Lett. 2000, 2, 2019-2022.
[58] Y. Wang, S. Chackalamannil, Z. Hu, J. W. Clader, W. Greenlee, W. Billard, H. Binch, G. Crosby, V. Ruperto, R. A. Duffy, R. McQuade, J. E. Lachowicz, Bioorg. Med. Chem. Lett. 2000, 10, 2247-2250.
[59] T. Iwasaki, Y. Maegawa, Y. Hayashi, T. Ohshima, K. Mashima, J. Org. Chem. 2008, 73, 5147–5150.
[60] G. Cai, Y. Fu, Y. Li, X. Wan, Z. Shi, J. Am. Chem. Soc. 2007, 129, 7666-7673.
[61] H. Horiguchi, H. Tsurugi, T. Satoh, M. Miura, J. Org. Chem. 2008, 73, 1590-1592.
[62] G. Zou, J. Guo, Z. Wang, W. Huanga, J. Tang, The Royal Society of Chemistry. 2007, 3055–3064.
[63] S. Hanada, A. Yuasa, H. Kuroiwa, Y. Motoyama, H. Nagashima, Eur. J. Org. Chem. 2010, 1021–1025.
[64] K. Miura, M. Tomita, J. Ichikawa, A. Hosomi, Org. Lett. 2008, 10, 133–136.
[65] Z. –L. Shen, K. K. K. Goh, C. H. A. Wong, Y. –S. Yang, Y. –C. Lai, H. –L. Cheong, T. –P. Loh, Chem. Commun. 2011, 47, 4778–4780.
[66] Y. Iuchi, Y. Obora, Y. Ishii, J. Am. Chem. Soc. 2010, 132, 2536–2537.
[67] X. Luo, H. Zhang, H. Duan, Q. Liu, L. Zhu, T. Zhang, A. Lei, Org. Lett. 2007, 22, 4571–4574.
[68] G. A. Molander, C. –S. Yun, Tetrahedron. 2002, 58, 1465 –1470.
[69] L. H. Schwartz, J. Landis, S. B. Lazarus, S. H. Stoldt, J. Org. Chern. 1972, 37, 1979 –1984.
[70] R. Ruzicka, L. Bara´kova´, P. Kla´n, J. Phys. Chem. B. 2005, 109, 9346-9353.
[71] M. Johnson, S. Connelly, A. Wilson, W. Kelly, J. Med. Chem. 2008, 51, 6348–6358.
[72] K. Ratheesh Kumar, R. Gopidas, Tetrahedron Letters. 2011, 52, 3102–3105.
[73] Z. –L. Shen, K. K. K. Goh, Y. –S. Yang, Y. –C. Lai,C. H. A. Wong, H. –L. Cheong, T. –P. Loh, Angew. Chem. Int. Ed. 2011, 50, 511 –514.
[74] F. Berhal, O. Esseiva, Charles-Henri Martin, H. Tone, Jean-Pierre Genet, T. Ayad, V. Ratovelomanana-Vidal, Org. Lett. 2011, 13, 2806 –2809.
[75] X. Feng, Y. Wang, B. Wei, J. Yang, H. Du, Org. Lett. 2011, 13, 3300 –3303.
[76] C. –G. Feng, Z. –Q. Wang, C. Shao, M. –H. Xu, G. –Q. Lin, Org. Lett. 2008, 10, 4101 –4104.
[77] Y. Zhao, L. Jin, P. Li, A. Lei, J. Am. Chem. Soc. 2008, 130, 9429–9433.
[78] M. P. DeMartino, K. Chen, P. S. Baran, J. Am. Chem. Soc. 2008, 130, 11546–11560.
[79] N. J. A. Martin, B. List, J. Am. Chem. Soc. 2006, 128, 13368-13369.
[80] Z. –L. Shen, H. –L. Cheong, T. –P. Loh, Tetrahedron Letters. 2009, 15, 1051–1054.
[81] P. Jones, Ch. K. Reddy, P. Knochel, Tetrahedron. 1998, 54, 1471 –1490.
[82] M. L. Kantam, R. Chakravarti, V. R. Chintareddy, B. Sreedhar, S. Bhargavac, Adv. Synth. Catal., 2008, 350, 2544 – 2550.


連結至畢業學校之論文網頁點我開啟連結
註: 此連結為研究生畢業學校所提供,不一定有電子全文可供下載,若連結有誤,請點選上方之〝勘誤回報〞功能,我們會盡快修正,謝謝!
QRCODE
 
 
 
 
 
                                                                                                                                                                                                                                                                                                                                                                                                               
第一頁 上一頁 下一頁 最後一頁 top
無相關期刊