請用此 Handle URI 來引用此文件: http://hdl.handle.net/11455/16834
標題: 1. 鐵催化芳香基硫醇與芳香基碘化物之交互耦合反應 2. 銅催化氫氧化銫與芳香基碘化物之交互耦合反應
1. Iron-catalyzed cross-coupling reaction of aryl thiols with aryl iodides 2. Copper-catalyzed C-O bond cross-coupling of CsOH with aryl iodides
作者: 吳誌濡
Wu, Jhih-Ru
關鍵字: Iron

Copper
cross-coupling reaction
thiol
CsOH

交互耦合反應
硫醇
氫氧化銫
出版社: 化學系所
引用: (1) Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1439. (2) (a) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442. (b) Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054. (3) (a) Cornils, B.; Herrmann, W. Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 1-2; Wiley-VCH: Weinheim, 1996. (b) Diedreich, F.; Stang, P. J. Metal-catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 1998. (c) Malleron, J.; Fiaud, J.; Legros, J. Handbook of Palladium-Catalyzed Organic Reactions; Academic Press: San Diego, 1997. (d) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, 1995. (4) Huang, J.; Nolan, S. P. J. Am. Chem. Soc. 1999, 121, 9889. (5) Agrofoglio, L. A.; Gillaizeau, I.; Saito, Y. Chem. Rev. 2003, 103, 1875. (6) Suzuki, A. Acc. Chem. Res. 1982, 15, 178. (7) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033. (8) Migita, T. Chem. Lett. 1977, 301. (9) Negishi, E.; King, A. O.; Okukado, N. J. Org. Chem. 1977, 42, 1821. (10) Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471. (11) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467. (12) Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979. (13) (a) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (b) Ullmann, F.; Bielecki, J. Chem. Ber. 1901, 34, 2174. (14) (a) Goldberg, I. Ber. Dtsch. Chem. Ges. 1906, 39, 1691. (b) Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4120. (15) (a) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653. (b) Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369. (c) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (16) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337. (17) Liu, G.; Huth, J. R.; Olejniczak, E. T.; Mendoza, R.; DeVries, P.; Leitza, S.; Reilly, E. B.; Okasinski, G. F.; Fesik, S. W.; von Geldern, T. W. J. Med. Chem. 2001, 44, 1202. (18) Itoh, T.; Mase, T. Org. Lett. 2007, 9, 3687. (19) (a) Kwaret, H.; Evans, E. R. J. Org. Chem. 1966, 31, 410. (b) Newman, M. S.; Karnes, H. A. J. Org. Chem. 1966, 31, 3980. (c) Delogu, G.; Fabbri, D.; Dettori, M. A. Tetrahedron: Asymmetry 1998, 9, 2819. (20) Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. (21) (a) Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett. 1978, 7, 13. (b) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385. (c) Kosugi, M.; Ogata, T.; Terada, M.; Sano, H.; Migita, T. Bull. Chem. Soc. Jpn. 1985, 58, 3657. (22) Schopfer, U.; Schlapbach, A. Tetrahedron 2001, 57, 3069. (23) Itoh, T.; Mase, T. Org. Lett. 2004, 6, 4587. (24) Mispelaere-Canivet, C.; Spindler, J.-F.; Perrio, S.; Beslin, P. Tetrahedron 2005, 61, 5253. (25) Murata, M.; Buchwald, S. L. Tetrahedron 2004, 60, 7397. (26) (a) Fernandez-Rodriguez, M. A.; Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180. (b) Fernandez-Rodriguez, M. A.; Shen, Q.; Hartwig, J. F. Chem. Eur. J. 2006, 12, 7782. (c) Fernandez-Rodriguez, M. A.; Hartwig, J. F. J. Org. Chem. 2009, 74, 1663. (27) Percec, V.; Bae, J.-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 6895. (28) Wong, Y.-C.; Jayanth, T. T.; Cheng, C.-H. Org. Lett. 2006, 8, 5613. (29) (a) Reddy, V. P.; Swapna, K.; Kumar, A. V.; Rao, K. R. J. Org. Chem. 2009, 74, 3189. (b) Reddy, V. P.; Kumar, A. V.; Swapna, K.; Rao, K. R. Org. Lett. 2009, 11, 1697. (30) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517. (31) Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803. (32) Jogdand, N. R.; Shingate, B. B.; Shingare, M. S. Tetrahedron Lett. 2009, 50, 6092. (33) Ku, X.; Huang, H.; Jiang, H.; Liu, H. J. Comb. Chem. 2009, 11, 338. (34) Correa, A.; Carril, M.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 2880. (35) Wu, W.-Y.; Wang, J.-C.; Tsai, F.-Y. Green Chem. 2009, 11, 326. (36) Buchwald, S. L.; Bolm, C. Angew. Chem., Int. Ed. 2009, 48, 5586. (37) (a) Fürstner, A.; Leitner, A.; Mendez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856. (b) Benjamin, D. S.; Alois, F. Acc. Chem. Res. 2008, 41, 1500. (38) Noda, D.; Sunada, Y.; Hatakeyama, T.; Nakamura, M.; Nagashima, H. J. Am. Chem. Soc. 2009, 131, 6078. (39) Tyman, J. H. P. Synthetic and Natural Phenols; Elsevier: New York, 1996. (40) Fujimoto, K.; Tokuda, Y.; Maekawa, H.; Matsubara, Y.; Mizuno, T.; Nishiguchi, I. Tetrahedron 1996, 52, 3889. (41) (a) Hoarau, C.; Pettus, T. R. R. Synlett 2003, 127. (b) Hanson, P.; Jones, J. R.; Taylor, A. B.; Walton, P. H.; Timms, A. W. J. Chem. Soc., Perkin Trans. 2 2002, 1135. (c) George, T.; Mabon, R.; Sweeney, G.; Sweeney, J. B.; Tavassoli, A. J. Chem. Soc., Perkin Trans. 1 2000, 2529. (d) Sweeney, J. B. Contemp. Org. Synth. 1997, 4, 435. (e) Schmidt, R. J. Appl. Catal. A 2005, 280, 89. (f) Bal, R.; Tada, M.; Sasaki, T.; Iwasawa, Y. Angew. Chem., Int. Ed. 2006, 45, 448. (42) Alonso, D. A.; Najera, C.; Pastor, I. M.; Yus, M. Chem. Eur. J. 2010, 16, 5274. (43) (a) Henry, P. M. J. Org. Chem. 1971, 36, 1886. (b) Stock, L. M.; Tse, K.; Vorvick, L. J.; Walstrum, S. A. J. Org. Chem. 1981, 46, 1757. (c) Niwa, S.; Eswaramoorthy, M.; Nair, J.; Raj, A.; Itoh, N.; Shoji, H.; Namba, T.; Mizukami, F. Science 2002, 295, 105. (44) Yoneyama, T.; Crabtree, R. H. J. Mol. Catal. A 1996, 108, 35. (45) Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300. (46) Neufeldt, S. R.; Sanford, M. S. Org. Lett. 2010, 12, 532. (47) Desai, L. V.; Malik, H. A.; Sanford, M. S. Org. Lett. 2006, 8, 1141. (48) Wang, G. W.; Yuan, T. T.; Wu, X. L. J. Org. Chem. 2008, 73, 4717. (49) Zhang, Y. H.; Yu, J. Q. J. Am. Chem. Soc. 2009, 131, 14654. (50) (a) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400. (b) Carril, M.; San Martin, R.; Dominguez, E. Chem. Soc. Rev. 2008, 37, 639. (51) Punniyamurthy, T.; Rout, L. Coord. Chem. Rev. 2008, 252, 134. (52) Chen, X.; Hao, X. S.; Goodhue, C. E.; Yu, J. Q. J. Am. Chem. Soc. 2006, 128, 6790. (53) Mathieu, D.; Bartoli, J. F.; Battioni, P.; Mansuy, D. Tetrahedron 2004, 60, 3855. (54) Taktak, S.; Flook, M.; Foxman, B. M.; Que, L.; Rybak-Akimova, E. V. Chem. Commun. 2005, 5301. (55) Maleczka Jr, R. E.; Shi, F.; Holmes, D.; Smith III, M. R. J. Am. Chem. Soc. 2003, 125, 7792. (56) Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 10694. (57) Chen, G.; Chan, A. S. C.; Kwong, F. Y. Tetrahedron Lett. 2007, 48, 473. (58) (a) Schulz, T.; Torborg, C.; Schaffner, B.; Huang, J.; Zapf, A.; Kadyrov, R.; Borner, A.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 918. (b) Sergeev, A.; Schulz, T.; Torborg, C.; Spannenberg, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 7595. (59) Gallon, B. J.; Kojima, R. W.; Kaner, R. B.; Diaconescu, P. L. Angew. Chem., Int. Ed. 2007, 46, 7251. (60) Kormos, C. M.; Leadbeater, N. E. Tetrahedron 2006, 62, 4728. (61) Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 8725. (62) Zhao, D.; Wu, N.; Zhang, S.; Xi, P.; Su, X.; Lan, J.; You, J. Angew. Chem., Int. Ed. 2009, 48, 8729. (63) Yang, D.; Fu, H. Chem. Eur. J. 2010, 16, 2366. (64) Jones, G. O.; Liu, P.; Houk, K. N.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 6205. (65) (a) Jenkins, C. L.; Kochi, J. K. J. Am. Chem. Soc. 1972, 94, 856. (b) Kochi, J. K. J. Am. Chem. Soc. 1957, 79, 2942. (66) (a) Whitesides, G. M.; Kendall, P. E. J. Org. Chem. 1972, 37, 3718. (b) Whitesides, G. M.; Fischer, W. F., Jr.; San Filippo, J., Jr.; Bashe, R. W.; House, H. O. J. Am. Chem. Soc. 1969, 91, 4871. (67) Johnson, C. R.; Dutra, G. A. J. Am. Chem. Soc. 1973, 95, 7783. (68) (a) Cohen, T.; Cristea, I. J. Am. Chem. Soc. 1976, 98, 748. (b) Cohen, T.; Lewarchik, F. J.; Tarino, J. Z. J. Am. Chem. Soc. 1974, 96, 7753. (c) Cohen, T.; Wood, J. Tetrahedron Lett. 1974, 15, 3555. (69) Wu, J.-R.; Lin, C.-H.; Lee, C.-F. Chem. Commun. 2009, 4450. (70) Willis, M. C. Angew. Chem., Int. Ed. 2007, 46, 3402. (71) (a) Caron, S.; Do, N. M.; Sieser, J. E.; Whritenour, D. C.; Hill, P. D. Org. Process Res. Dev. 2009, 13, 324. (b) Wada, C. K.; Holms, J. H.; Curtin, M. L.; Dai, Y.; Florjancic, A. S.; Garland, R. B.; Guo, Y.; Heyman, H. R.; Stacey, J. R.; Steinman, D. H.; Albert, D. H.; Bouska, J. J.; Elmore, I. N.; Goodfellow, C. L.; Marcotte, P. A.; Tapang, P.; Morgan, D. W.; Michaelides, M. R.; Davidsen, S. K. J. Med. Chem. 2002, 45, 219. (c) Liu, L.; Siegmund, A.; Xi, N.; Kaplan-Lefko, P.; Rex, K.; Chen, A.; Lin, J.; Moriguchi, J.; Berry, L.; Huang, L.; Teffera, Y.; Yang, Y.; Zhang, Y.; Bellon, S. F.; Lee, M.; Shimanovich, R.; Bak, A.; Dominguez, C.; Norman, M. H.; Harmange, J. C.; Dussault, I.; Kim, T. S. J. Med. Chem. 2008, 51, 3688. (d) Hodous, B. L.; Geuns-Meyer, S. D.; Hughes, P. E.; Albrecht, B. K.; Bellon, S.; Bready, J.; Caenepeel, S.; Cee, V. J.; Chaffee, S. C.; Coxon, A.; Emery, M.; Fretland, J.; Gallant, P.; Gu, Y.; Hoffman, D.; Johnson, R. E.; Kendall, R.; Kim, J. L.; Long, A. M.; Morrison, M.; Olivieri, P. R.; Patel, V. F.; Polverino, A.; Rose, P.; Tempest, P.; Wang, L.; Whittington, D. A.; Zhao, H. J. Med. Chem. 2007, 50, 611. (72) (a) Laskoski, M.; Dominguez, D. D.; Keller, T. M. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 4559. (b) Labadie, J. W.; Hedrick, J. L.; Ueda, M. Am. Chem. Soc. Symp. Ser. 1996, 624, 210. (73) (a) Draper, W. M.; Casida, J. E. J. Agric. Food Chem. 1983, 31, 227. (b) Draper, W. M.; Casida, J. E. J. Agric. Food Chem. 1983, 31, 1201. (c) Scrano, L.; Bufo, S. A.; D''Auria, M.; Meallier, P.; Behechti, A.; Shramm, K. W. J. Environ. Qual. 2002, 31, 268. (74) (a) Tan, E. S.; Miyakawa, M.; Bunzow, J. R.; Grandy, D. K.; Scanlan, T. S. J. Med. Chem. 2007, 50, 2787. (b) Nicolaou, K. C.; Boddy, C. N. C.; Brase, S.; Winssinger, N. Angew. Chem., Int. Ed. 1999, 38, 2096. (75) (a) Burgos, C. H.; Barder, T. E.; Huang, X.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 4321. (b) Shelby, Q.; Kataoka, N.; Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 10718. (c) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224. (d) Schwarz, N.; Pews-Davtyan, A.; Alex, K.; Tillack, A.; Beller, M. Synthesis 2007, 3722. (e) Harkal, S.; Kumar, K.; Michalik, D.; Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Beller, M. Tetrahedron Lett. 2005, 46, 3237. (f) Hu, T.; Schulz, T.; Torborg, C.; Chen, X.; Wang, J.; Beller, M.; Huang, J. Chem. Commun. 2009, 7330. (76) Marcoux, J. F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539. (77) (a) Frlan, R.; Kikelj, D. Synthesis 2006, 2271. (b) Sawyer, J. S. Tetrahedron 2000, 56, 5045. (c) Lindley, J. Tetrahedron 1984, 40, 1433. (78) (a) Xia, N.; Taillefer, M. Chem. Eur. J. 2008, 14, 6037. (b) Zhang, Q.; Wang, D.; Wang, X.; Ding, K. J. Org. Chem. 2009, 74, 7187. (c) D''Angelo, N. D.; Peterson, J. J.; Booker, S. K.; Fellows, I.; Dominguez, C.; Hungate, R.; Reider, P. J.; Kim, T. S. Tetrahedron Lett. 2006, 47, 5045. (d) Ouali, A.; Spindler, J. F.; Cristau, H. J.; Taillefer, M. Adv. Synth. Catal. 2006, 348, 499. (e) Lipshutz, B. H.; Unger, J. B.; Taft, B. R. Org. Lett. 2007, 9, 1089. (f) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954. (g) Cai, Q.; Zou, B. L.; Ma, D. Angew. Chem., Int. Ed. 2006, 45, 1276. (h) Cai, Q.; He, G.; Ma, D. J. Org. Chem. 2006, 71, 5268. (i) Takeuchi, D.; Asano, I.; Osakada, K. J. Org. Chem. 2006, 71, 8614. (j) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450. (k) Chen, Y.-J.; Chen, H.-H. Org. Lett. 2006, 8, 5609. (l) Ma, D.; Cai, Q. Org. Lett. 2003, 5, 3799. (m) Lv, X.; Bao, W. L. J. Org. Chem. 2007, 72, 3863. (n) Schareina, T.; Zapf, A.; Cotte, A.; Mueller, N.; Beller, M. Synthesis 2008, 3351. (o) Maiti, D.; Buchwald, S. L. J. Org. Chem. 2010, 75, 1791. (79) Rout, L.; Saha, P.; Jammi, S.; Punniyamurthy, T. Eur. J. Org. Chem. 2008, 4, 640. (80) Wu, Y.-J.; He, H. Synlett 2003, 1789. (81) Ranu, B. C.; Saha, A.; Jana, R. Adv. Synth. Catal. 2007, 349, 2690. (82) Raulins, N. R.; Sibert, L. A. J. Org. Chem. 1961, 26, 1382. (83) Liu, H.; Wang, M.; Wang, Y.; Gu, Q.; Sun, L. Synth. Commun. 2007, 37, 3815. (84) Lara, P.; Paneque, M.; Poveda, M. L.; Salazar, V.; Santos, L. L.; Carmona, E. J. Am. Chem. Soc. 2006, 128, 3512. (85) Smith, H. A.; Stump, B. L. J. Am. Chem. Soc. 1961, 83, 2739. (86) Zhou, Y.; Gao, G.; Li, H.; Qu, J. Tetrahedron Lett. 2008, 49, 3260. (87) Dannley, R. L.; Hoffman, R. V. J. Org. Chem. 1975, 40, 2426. (88) Wilson, C. J.; Wenzke, H. H. J. Am. Chem. Soc. 1935, 57, 1265. (89) Ghosh, R.; Samuelson, A. G. New J. Chem. 2004, 28, 1390. (90) Gorczynski, M. J.; Leal, R. M.; Mooberry, S. L.; Bushweller, J. H.; Brown, M. L. Bioorg. Med. Chem. 2004, 12, 1029. (91) Gujadhur, R.; Venkataraman, D. Synth. Commun. 2001, 31, 2865.
摘要: 在本論文的第一部分中,我們主要探討在三氯化鐵(10 mol%)與雙牙基磷配體(10 mol%)的搭配下,提供一個有效的催化系統在芳香基碘化物與芳香基硫醇的硫醚化反應。此系統顯示出有高度的官能基容忍度。 在第二部分中,我們證明在密閉的系統中,銅催化碳-氧鍵交互耦合反應可以在無添加額外配位基的條件下有效的進行反應。更感興趣的是使用氫氧化銫與兩種不同的芳香基碘化物,在2-吡啶甲酸的輔助下,能夠成功的進行具有選擇性的兩次碳-氧鍵交互耦合反應,首次在一鍋反應中形成不對稱型醚類。
In the first part of this thesis, we have demonstrated that the combination of FeCl3 (10 mol%) with bisphosphines (10 mol%) proves to be an efficient catalytic system for thioetherification of aryl iodides with aryl thiols. This system shows good functional group tolerance. In the second part, we have shown that in sealed condition, the copper-catalyzed C-O coupling reaction can be performed very well without any additive ligand. Interesting, the double C-O coupling reaction of CsOH with two different aryl iodides can be successfully performed with excellent selectivity in the presence of picolinic acid as a ligand, forming asymmetric diaryl ether in one-pot for the first time.
URI: http://hdl.handle.net/11455/16834
其他識別: U0005-2907201014385100
顯示於類別:化學系所

文件中的檔案:
沒有與此文件相關的檔案。


在 DSpace 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。