請用此 Handle URI 來引用此文件: http://hdl.handle.net/11455/16795
標題: 1.利用水楊酸配位基進行銅催化氯苯和溴苯與氨水交互耦合反應之研究 2.雌激素對抗劑(DMA)合成之研究
1. The study in copper-catalyzed cross-coupling of aryl chlorides and bromides with aqueous ammonia using salicyclic acid as a ligand 2. The study in the synthesis of desmethylated arzoxifene (DMA)
作者: 連瑞政
Lian, Ruei-Jeng
關鍵字: copper

salicyclic acid
ammonia
DMA
水楊酸
氨水
雌激素
出版社: 化學系所
引用: 第柒章、參考文獻 1. Tasler, S. ; Mies, J.; Lang, M. Adv. Synth. Catal., 2007, 349, 2286. 2. Shirota, Y.; Kageyama, H. Chem. Rev., 2007, 107, 953. 3. a) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682. b) Razzuk, A.; Biehl, E. R. J. Org. Chem. 1987,52, 2619. 4. Ma, D.; Xia, C.; Jiang, J.; Zhang, J.; Tang, W. J. Org. Chem. 2003, 68, 442. 5. Beletskaya, I. P.; Cheprakov, A. V. Coordination Chemistry Reviews 2004, 248, 2337. 6. Muci, A. R.; Buchwald, S. L. Topic in Current Chemistry, Vol. 219, Springer-Verlag Berlin Heidelberg 2002, page 1-9. 7. Agrofoglio, L. A.; Gillaizeau, I.; Saito, Y. Chem. Rev. 2003, 103, 1875 8. a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467. b) Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627. c) Cassar, L. J. Organomet. Chem. 1975, 93, 253. d) Dieck, H. A.; Heck, R. F. J. Organomet. Chem. 1975, 93, 259. 9. a) Mitchell, T. N. Synthesis 1992, 803. b) Kosugi, M.; Sasazawa, K.; Shimuzi, Y.; Migita, T. Chem. Lett. 1977, 301. c) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033. d) Piers, E.; Friesen, R. W.; Keay, B. A. Tetrahedron 1991, 47, 4555. 10.a) Miyaura, N., Suzuki, A. Chem. Rev. 1995, 95, 2457. b) Snieckus, V.Chem. Rev. 1990, 90, 879. c) Matteson, D. S. Tetrahedron 1989, 45, 1859. d) Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437. e) Miyaura, N.; Sato, M.; Suzuki, A. Tetrahedron Lett. 1986, 27, 3745. 11. Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5518. 12. The Chemistry of Organozinc Compounds; Rappoport, Z.; Marek, I.Eds.; Wiley: New York, 2006; Chapter 11. 13. Muci, A. R.; Buchwald, S. L. Topic in Current Chemistry, Vol. 219, Springer-Verlag Berlin Heidelberg 2002, page 131-209. 14. Meyers, C.; Maes, Bert U. W.; Loones, Kristof T. J.; Bal, G.; Guy, L. F.; Dommisse, R. A J. Org. Chem. 2004, 69, 6010 15. a) Deng, W; Wang, Y. F.; Zou, Y.; Liu, L. Guo, Q. X. Tetrahedron Letter,2004, 45, 2311.; b) Klapars, A.; Huang, X.; Buchwald, S.L. J. Am. Chem. Soc., 2002, 124, 7421.; c) Antilla, J. C.; Klapars, A.; Buchwald, S.L. J. Am. Chem. Soc., 2002, 124, 11684.; d) Deng, W; Wang, Y. F.; Zou, Y.; Liu, L. Guo, Q. X. Synlett, 2004, 6010. 16. Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Tetrahedron Letters 2002 ,43, 7143. 17. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. 18. a) Ullmann, F. Chem. Ber. 1901, 34, 2174. b) Ullmann, F. Chem. Ber. 1903, 36, 2382. c) Ullmann, F.; Sponagel, P. Chem. Ber. 1905, 36, 2211. d) Hurtley, W. R. H. J. Chem. Soc. 1929, 1870 19.Goldberg, I. Chem. Ber. 1906, 39, 1691. 20.Lindley, J. Tetrahedron Lett. 1984, 40, 1433. 21.a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. b) Antilla, T.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684. c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. 22.a) Shen, R.; Porco, J. A., Org. Lett. 2000, 2, 1333.; b) Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803.;c) Crawford, K. R.; Padwa, A. Tetrahedron Letter,2002, 43, 7365.; d) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421 23.Evano, G.; Blannchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054. 24.a) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315. b) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748. c) Kienle, M.; Dubbaka, S.; R.; Brade, K.; Knochel, P. Eur. J. Org. Chem. 2007, 4166. 25.a) Gujadhur, R.; Venkataraman, D. Synth. Commun. 2001, 38, 2865. b) Xie, X.; Cai, G.; Ma, D. Org. Lett. 2005, 7, 4693. c) Jiang, Y.; Wu, N.; Wu, H.; He, M. Synlett. 2005, 2731. d) Pei, L.; Qian,W. Synlett. 2006, 1719. 26.a) Monnier, F.; Turtaut, F.; Duroure, L.; Taillefer, M. Org. Lett. 2008, 10, 3203 b) 陳鴻志論文, 2009, 國立中興大學陳耀鐘老師實驗室c)黃華民論文, 2008, 國立中興大學陳耀鐘老師實驗室 d) 胡世憲論文,2009,國立中興大學陳耀鐘老師實驗室。 27.Chen, Y. J.; Chen, H. H. Org. Lett. 2006, 8, 5609. 28.Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428. 29.a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. b) Leeuwena, PietW. N. M. van.; Strijdonck, Gino P. F. van. Tetrahedron Letters , 2005, 46, 2405. c) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 3799. d) Antilla, J. C.; Baskin, J. C. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578. 30.Gujadhur, R. K; Bates, C. G.; Venkataraman, D. Org. Lett., 2001, 3, 4315. 31.Zhang, S. L.; Liu, L.; Fu, Y.; Guo, Q. X. Organometallics, 2007, 26, 4546. 32.a)Gujadhur, R. K; Bates, C. G.; Venkataraman, D. Org. Lett., 2001, 3, 4315. b) Pu, Y.-M.; Ku, Y.-Y.; Grieme, T.; Henry, R.; Bhatia, A. V. Tetrahedron Lett. 2006, 47, 149.c) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748. 33.Evano, G.; Blannchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054. 34.Mallesham, B.; Rajesh, B. M.; Reddy, P. R.; Srinivas, D.; Trehan, S. Org. Lett. 2003, 5, 963. 35. Shafir, A.; Lichtor, P. A.; Buchwald, S. L. J. Am.Chem. Soc. 2007,129, 3490. 36.Fagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo,A. J. Am. Chem. Soc. 2000, 122, 5043. 37.Hosseinzadeh, R.; Tajbakhsh, M.; Mohadjerani, M.; Alikarami, M.Synlett 2005, 1101. 38.Dang, C.-L.; Xie, Y.-X.; Yin, D.-L.; Li, J.-H. Synthesis 2006, 3370 39. a) Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164.b) Liu, L.; Frohn, M.; Xi, N.; Dominguez, C.; Hungate, R.; Reider,P. J. J. Org. Chem. 2005, 70, 10135. 40. Ma, D.; Liu, F. Chem. Commun. 2004, 1934. 41. a) Xin, L.; Weiliang, B. J. Org. Chem. 2007, 72, 3863. b) Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623. c) Tanimori, S.; Ura, H.; Kirihata, M. Eur. J. Org. Chem. 2007, 3977. d) Kwong, Y. F.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 3517. e) Kwong, Y. F.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581. 42. Larock, R. C. Comprehensive Organic Transformation: a guide to functional group preparation, 2nd edn., Wiley-VCH, New York, 1999. 43. Roundhill, D. M. Chem. Rev. 1992, 92, 1–27. 44. Zhao, J.; Goldman, A. S.; Hartwig, J. F. Science 2005, 307, 1080. 45. Wolfe, J. P.; Ahman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. Tetrahedron Lett., 1997, 38, 6367. 46. Jaime-Figueroa, S.; Liu, Y.; Muchowski, J. M.; Putman, D.G. Tetrahedron Lett., 1998, 39, 1313. 47. Lee, S.; Jorgensen, M.; Hartwig, J. F.; Org. Lett., 2001, 3, 2729. 48. For publications on palladium catalyzed amination using ammonia, see: a) Schulz, T.; Torborg, C.; Enthaler, S.; Schaffner, B.; Dumrath, A.; Spannenberg, A.; Neumann, H.; Borner, A.; Beller, M. Chem.–Eur. J., 2009, 15, 4528; b) Vo, G. D.; Hartwig,J. F. J. Am. Chem. Soc., 2009, 131, 11049; c) Shen, Q.;Hartwig, J. F. J. Am. Chem. Soc., 2006, 128, 10028; d) Surry, D. S.; Buchwald, S. L. J. Am. Chem. Soc., 2007, 129, 10354. 49. For publications on copper catalyzed amination using ammonia, see: a) Ntaganda, R. ; Dhudshia, B. ; Macdonald, C. L. B. ; Thadani, A. N. Chem. Commun., 2008, 6200. b) Kim, J. ; Chang, S. Chem. Commun., 2008, 3052. c) Taillefer , M.; Xia, N. 2007, Fr 2007/06827; d) Xia , N.; Taillefer, M. Angew. Chem., Int. Ed., 2009, 48, 337. e) Jiang, L.; Lu, X.; Zhang, H. ; Jiang , Y.; Ma, D. J. Org. Chem., 2009, 74, 4542. f) Xu, H.; Wolf, C. Chem. Commun., 2009, 3035. g) Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. Angew. Chem., Int. Ed., 2009, 48, 1114. h) Elmkaddem, M. K.; Fischmeister, C.; Thomas, C. M.; Renaud, J. L. Chem. Commun., 2010, 925 50. Ding, K.; Zannat, F.; Morris, J. C.; Brennessel, W. W.; Holland, P.L. ; J. Organomet. Chem. 2009, 694, 4204. 51. Palkowitz, A. D.; Glasebrook, A. L.; ThRasher, J.; Hauser, K. L.; Short, L. L.; Phillips, D. L.; Muehl, B. S.; Sato, M.; Shetler, P. K.; Cullinan, G. J.; Pell, T. R.; Bryant, H. U. J. Med. Chem. 1997, 40, 1407. 52. Castanet, A.S.; Colobert, F.; Broutin, P.E. Tetrahedron Lett., 2002, 43, 5047. 53. Gao, X.; Fu, H.; Qiao,R.; Jiangand, Y.; Zhao, Y. J. Org. Chem., 2008, 73, 6864. 54. Rahaim, R. J., Jr. ; Maleczka, R. E., Jr. Org. Lett., 2005, 7, 5087. 55. Roy, A. D.; Subramanian, A.; Roy, R. J. Org. Chem., 2006, 71, 382. 56. Cho, C. H.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. J. Comb. Chem. 2009, 11, 900. 57. Maiti, D.; Buchwald, S. L. J. Org. Chem., 2010, 75, 1791. 58. Motoyama, Y.; Kamo, K.; Nagashima, H. Org. Lett., 2009, 11, 1345.
摘要: 我們以氧化亞銅搭配水楊酸配位基成功的催化了氨水對氯苯以及溴苯進行交互耦合反應。而且這個系統符合現代綠色化學的訴求,並不需要有機溶劑即可進行反應。 Desmethylated arzoxifene(DMA)具有抗乳癌的功能。有別於以往的傳統合成方法,我們試著將銅金屬催化的C-C以及C-O耦合反應應用於此分子的全合成裡,希望能夠有效的縮短合成步驟。
We successfully use copper(I) oxide to catalyze cross-coupling of aryl chlorides and bromides with aqueous ammonia using salicyclic acid as a ligand. This system takes place without organic solvent which conformed to the demand of green chemistry. Desmethylated arzoxifene(DMA) has the capability to treat breast cancer. We tried to use copper-catalyzed cross-coupling reactions of C-C and C-O bonds to accomplish the total synthesis of Desmethylated arzoxifene which is different from the traditional synthesis method of Desmethylated arzoxifene. We hope to shorten the synthetic steps of DMA.
URI: http://hdl.handle.net/11455/16795
其他識別: U0005-1108201015023800
顯示於類別:化學系所

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