Please use this identifier to cite or link to this item: http://hdl.handle.net/11455/14554
標題: 探討銠金屬催化碳-硫鍵之交互耦合反應
Investigation of Rhodium-Catalyzed Carbon-Sulfur Bond Cross-Coupling Reaction
作者: 賴志昕
Lai, Chih-Shin
關鍵字: 交互耦合反應
cross-coupling
銠金屬
碳硫鍵
rhodium
C-S bond
出版社: 化學系所
引用: (1) (a) Liu, G.; Huth, J. R.; Olejniczak, E. T.; Mendoza, R.; De Vries, P.; Leitza, S.; Reilly, E. B.; Okasinski, G. F.; Fesik, S. W.; von Geldem, T. W. J. Med. Chem. 2001, 44, 1202; (b) De Martino, G.; La Regina, G.; Coluccia, A.; Edler, M. C.; Barbera, M. C.; Brancale, A.; Wilcox, E.; Hamel, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2004, 47, 6120. (2) Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1439. (3) (a) Tatumi, R.; Akita, T.; Fujihara, H. Chem. Commun. 2006, 3349; (b) Kang, S.-K.; Ryu, H.-C.; Lee, S.-W. J. Chem. Soc. Perkin Trans. 1 1999, 2661; (c) Fairlamb, Ian J. S. Ann. Rep. Prog. Chem., B: Org. Chem. 2006, 102, 50. (4) (a) Frost, C. G.; Mendonca, P. J. Chem. Soc. Perkin Trans. 1 1998, 2615; (b) Artamkina, G. A.; Ermolina, M. V.; Beletskaya, I. P. Mendeleev. Commun. 2003, 158; (c) Jerphagnon, T.; van Klink, G. P. M.; de Vries, J. G.; van Koten, G. Org. Lett. 2005, 7, 5241; (d) Xu, H.; Wolf, C. Chem. Commun. 2009, 3035. (5) (a) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224; (b) Kuwabe, S.; Torraca, K. E.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 12202. (6) (a) Zhang, Y.; Ngeow, K. C.; Ying, J. Y. Org. Lett. 2007, 9, 3495; (b) Reddy, V. P.; Swapna, K.; Kumar, A. V.; Rao, K. R. J. Org. Chem. 2009, 74, 3189. (7) Kondo, T.; Mitsudo, T.-a. Chem. Rev. 2000, 100, 3205 (8) (a) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385; (b) Itoh, T.; Mase, T. Org. Lett., 2004, 6, 4587; (c) Fernandez-Rodriguez, M. A.; Shen Q.; Hartwig J. F. J. Am. Chem. Soc. 2006, 128, 2180; (d) Fernandez-Rodriguez, M. A.; Shen Q.; Hartwig, J. F. Chem. Eur. J. 2006, 12, 7782; (e) Fernandez-Rodriguez, M. A.; Hartwig, J. F. J. Org. Chem. 2009, 74, 1663; (f) Alvaro, E.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 7858; (g) Sayah, M.; Organ, M. G. Chem. Eur. J. 2011, 17, 11719. (9) (a) Zhang, Y.; Ngeow, K. N.; Ying, J. Y. Org. Lett. 2007, 9, 3495; (b) Percec, V.; Bae, J.-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 6895. (10) Wong, Y.-C.; Jayanth, T. T.; Cheng, C.-H. Org. Lett. 2006, 8, 5613. (11) (a) Larsson, P.-F.; Correa, A.; Carril, M.; Norrby, P.-O.; Bolm, C. Angew. Chem. Int. Ed. 2009, 48, 5691; (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517; (c) Carril, M.; SanMartin, R.; Dominguez, E.; Tellitu, I. Chem. Eur. J. 2007, 13, 5100. (12) Reddy, V. P.; Kumar, A. V.; Swapna, K.; Rao, K. R. Org. Lett. 2009, 11, 1697. (13) Jean, M.; Renault, J.; van de Weghe, P.; Asao, N. Tetrahedron Lett. 2010, 51, 378. (14) (a) Wu, J.-R.; Lin, C.-H.; Lee, C.-F. Chem. Commun. 2009, 4450; (b) Correa, A.; Carril, M.; Bolm, C. Angew. Chem. Int. Ed. 2008, 47, 2880. (15) (a) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett., 2000, 2 , 2019; (b) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett., 2002, 4, 4309. (16) (a) Ajiki, K.; Hirano, M.; Tanaka, K. Org. Lett. 2005, 7, 4193; (b) Arisawa, M.; Suzuki, T.; Ishikawa, T.; Yamaguchi, M. J. Am. Chem. Soc. 2008, 130, 12214. (17) (a) Xu, H.-J.; Zhao, X.-Y.; Feng, Y.-S.; Deng, J.; Fu, Y. Synlett 2008, 19, 3063. (b) Litaudon, M.; Trigalo, F.; Martin, M.-T.; Frappier, F.; Guyot, M. Tetrahedron 1994, 50, 5323. (c) Lee, A. H. F.; Chen, J.; Liu, D.; Leung, T. Y. C.; Chan, A. S. C.; Li, T. J. Am. Chem. Soc. 2002, 124, 13972. (d) Freydank, A. C.; Humphrey, M. G.; Friedrich, R. W.; Luther-Davies, B. Tetrahedron 2002, 58, 1425. (e) Zhang, H.; Cao, W.; Ma, D. Synth. Commun. 2007, 37, 25. (f) Heynderickx, A.; Samat, A.; Guglielmetti, R. Synthesis 2002, 1747. (18) (a) Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596. (b) Eichman, C. C.; Stambuli, J. P. Molecules 2011, 16, 590. (c) Beletskaya, I. P.;Ananikov, V. P. Eur. J. Org.Chem. 2007, 3431. (d)Ley, S.V.;Thomas, A. W. Angew. Chem., Int. Ed. 2003, 43, 5400. (e) Procter, D. J. J. Chem. Soc., Perkin Trans. 1 2001, 335. (f) Lindley, J. Tetrahedron 1984, 40, 1433. (19) Kondoh, A.; Takami, K.; Yorimitsu, H.; Oshima, K. J. Org. Chem. 2005, 70, 6468. (20) Murahashi, S.-I.; Yamamura, M.; Yanagisawa, K.; Mita, N.; Kondo, K. J. Org. Chem. 1979, 44, 2408. (21) Liu, Y.; Bao, W. Tetrahedron Lett. 2007, 48, 4785. (22) Kabir, M. S.; Linn, M. L. V.; Monte, A.; Cook, J. M. Org. Lett. 2008, 10, 3363. (23) Yatsumonji, Y.; Okada, O.; Tsubouchi, A.; Takeda, T. Tetrahedron 2006, 62, 9981. (24) Lee, J.-Y.; Lee, P. H. J. Org. Chem. 2008, 73, 7413. (25) Bandaru, M.; Sabbavarpu, N. M.; Katl, R.; Yadavalli, V. D. N. Chem. Lett. 2010, 39, 1149. (26) Imazaki, Y.; Shirakawa, E.; Hayashi, T. Tetrahedron 2011, 67, 10212. (27) (a) Review: Arisawa, M.; Yamaguchi, M. Pure Appl. Chem. 2008, 80, 993; (b) SS bond: Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2003, 125, 6624; (c) Arisawa, M.; Suwa, A.; Yamaguchi, M. J. Organomet. Chem. 2006, 691, 1159; (d) CH and CS bond: Arisawa, M.; Fujimoto, K.; Morinaka, S.; Yamaguchi, M. J. Am. Chem. Soc. 2005, 127, 12226; (e) Arisawa, M.; Kubota, T.; Yamaguchi, M. Tetrahedon Lett. 2008, 49, 1975; (f) PP and PS bonds: Arisawa, M.; Ono, T.; Yamaguchi, M. Tetrahedron Lett. 2005, 46, 5669. (28) Arisawa, M.; Fujimoto, K.; Yamaguchi, M. Unpublished results. (29) Kao, H.-L.; Chen, C.-K.; Wang, Y.-J.; Lee, C.-F. Eur. J. Org. Chem., 2011, 1776. (30) Eichman, C. C.; Stambuli, J. P. J. Org. Chem., 2009, 74, 4005. (31) Schopfer, U.; Schlapbach, A. Tetrahedron, 2001, 57, 3069. (32) Yang, H.; Xi, C.; Miao, Z.; Chen, R. Eur. J. Org. Chem., 2011, 3353. (33) Park, N.; Park, K.; Jang, M.; Lee, S. J. Org. Chem., 2011, 76, 4371. (34) Wang, H.; Jiang, L.; Chen, T.; Li, Y. Eur. J. Org. Chem., 2010, 2324. (35) Duan, Z.; Ranjit, S.; Liu, X. Organic Letters, 2010, 12, 2430. (36) Ranu, B. C.; Saha, A. ; Jana, R. Adv. Synth. Catal., 2007, 349, 2690. (37) Zhang, X.-Y.; Zhang, X.-Y.; Guo, S.-R. J. Sulfur Chem. 2011, 32, 23. (38) Li, Y.; Nie,C.; Wang, H.; Li, X.; Verpoort, F.; Duan, C. Eur. J. Org. Chem. 2011, 7331. (39) Kao, H.-L.; Lee, C.-F. Org. Lett. 2011, 13, 5204.  
摘要: 在許多生物活性分子上常可以見到芳香基和烯基硫醚。也因為如此,已有許多方法來合成這些分子。在這些方法當中,傳統方法往往過於劇烈,相較之下過渡金屬催化交互耦合反應則能提供更溫和的反應條件。本論文第一部分描述銠金屬搭配PPh3進行芳香基碘化物與硫醇交互耦合反應。之後我們也探討利用銠金屬催化烯基硫醚的製備。有趣的是,在未加入烯基鹵化物以及硫醇之前,先使我們的催化系統充分攪拌有助於烯基硫醚產率的提升。
Aryl- and alkenyl thioethers are present in many biologically active molecules. As a consequence, many approaches have been described for the synthesis of these compounds. Among these methods, the transition-metal-catalyzed cross-coupling reaction of thiols with aryl halides provides an attractive choice for this purpose due to its mild reaction conditions when compared to traditional methods. In the first part of this thesis, the rhodium-catalyzed cross-coupling reaction of thiols with aryl iodides in the presence of PPh3 as a ligand is described. The preparation of alkenyl thioethers based on rhodium catalyst is also introduced. Interestingly, the chemical yields for alkenyl thioethers can be improved when the catalyst was stirred for a while before addition of thiols and vinyl halides.
URI: http://hdl.handle.net/11455/14554
其他識別: U0005-0608201204244400
文章連結: http://www.airitilibrary.com/Publication/alDetailedMesh1?DocID=U0005-0608201204244400
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