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標題: 以具氮及磷配位之含鈷雙牙配位基錯合之鈀金屬化合物催化胺化反應研究
Application of Cobalt-containing P∩N Ligands in Palladium Catalyzed Amination Reactions
作者: 蕭有成
Hsiao, You-Chen
關鍵字: Cobalt;氮及磷配位;Palladium;Catalyzed Amination reaction;含鈷雙牙配位基;鈀金屬;催化胺化反應
出版社: 化學系所
引用: 參考文獻 Miyaura, N.; Suzuki, A., Chem. Rev., 1995, 95, 2457-2483. Huang, J.; Nolan, S. P., J. Am. Chem. Soc., 1999, 121, 9889-9890. Littke, A. F.; Fu, G. C., Angew. Chem., 1999, 111, 2568-2570. Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem., 1972, 37, 2320-2322. (a) Kramareva, N.; Navarro, O.; Nolan. S. P., Org. Lett., 2005, 9, 1829. (b) Yin, J.; Rainka, M. P.; Zhang, X.-X.; Buchwald, S. L., J. Am. Chem. Soc., 2002, 124, 1162. (c) Zhou, J.; Fu, G. C., J. Am. Chem. Soc., 2004, 126, 1340. (a)Hamann, B. C.; Hartwig, J. F., J. Am. Chem. Soc., 1998, 120, 7369-7370. (b) Harris, M. C.; Buchwald, S. L., J. Org. Chem., 2000, 65, 5327-5333. Belfield, A. J., Tetrahedron, 1999, 55, 13285-13300. Josugi, M.; Kameyama, M.; Migita, T., Chem. Lett., 1983, 927-928 Wolfe, J. P.; Wagaw, S.; Buchwald, S. L., J. Am. Chem. Soc., 1996, 118, 7215-7216. Driver, M. S.; Hartwig, J. F., J. Am. Chem. Soc., 1996, 118, 7217-7218 Guram, A. S.; Rennels, R. A.; Buchwald, S. L., Angew. Chem. Int. Ed. , 1995, 34, 1348 Louie, J.; Hartwig, J. F., Tetrahedron Lett., 1995, 36, 3609. Verkade, J. G., J. Org. Chem., 2003, 68, 8416-4238. (a) Negwer, M., Organic-chemical drugs and their synonyms, 7th ed.; (b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D., Angew. Chem. Int. Ed., 2005, 44, 4442-4489. (c) Hage, R.; Lienk, A., Angew. Chem. Int. Ed., 2006, 45, 206-222. (d) Loutfy, R. O.; C. Hsiao, K.; Kazmaier P. M., Photogr. Sci. Eng., 1983, 27, 5-9. (e) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L., J. Am. Chem. Soc., 2005, 127, 4685-4696. (f) D’Aprano, G.; Leclerc, M.; Zotti, G.; Schiavon, G., Chem. Mater., 1995, 7, 33-42. (a) Wang, N.S.; Tsai .Y.M.; Hwu, T.Y.; Wong, K.T., macromolecules B natera. et. al., 2007, 7.5 (b) Zhou, G.; Wong, W.Y.; Yao, B.; Xie, Z.; Wang, L., Angew. Chem. Int. Ed., 2007, 46, 1149 –1151 Wang, W.; Ding, Q.; Fan, R.; Wu, J., Tetrahedron Letters., 2007, 48, 3647–3649 Parr, R. G.; Pearson, R. G., J. Am. Chem. Soc., 1983, 105, 7512-7516. Miura, M., Angew. Chem. Int. Ed., 2004, 43, 2201-2203. Colacot, T. J., Chem. Rev., 2003, 103, 3101-3118. Helmut, W., Organometallics, 2005, 24, 1036-1049. (a) Chang, Y. C.; Chang, C. P.; Huang, Y. L.; Hong, F. E., Dalton Trans, 2004, 157-165. (b) Chang, C. P.; Huang, Y. L.; Hong, F. E.,Tetrahedron, 2005, 61, 3835-3839. (c) Chang, Y. C.; Lee, J. C.; Hong, F. E., organometallics, 2005, 24, 5686-5695. (d) Lee, J. C.; Wang, M. G.; Hong, F. E., Eur. J. Inorg. Chem., 2005,5011-5017 Buchwald, S. L., J. Am. Chem. Soc., 1999, 121, 9550-9561. Crystal structures for related compounds are available from literatures: (a) Fernández-Galán, R.F.; Jalón, A.; Manzano, B. R.; Rodríguez-de la Fuente, J.; Vrahami, M.; Jedlicka, B.; Weissensteiner, W.; Jogl, G.,Organometallics, 1997, 16, 3758. (b) Vasconcelos, I. C. F. ; Rath, N. P.; Spilling, C. D., Tetrahedron: Asymmetry, 1998, 9, 937. (c) Wang, Y.; Li, X.; Sun, J.; Ding, K., Organometallics, 2003, 22, 1856. (d) Faller, J. W.; Sarantopoulos, N., Organometallics, 2004, 23, 2008. (e) Goldfuss, B.; Löschmann, T.; Rominger, F., Chem. Eur. J., 2004, 10, 5422. Crystal structures for related compounds are available from literatures: (a)Hegedus, L. S.; Akermark, B.; Olsen, D. J.; Anderson, O. P.; Zetterberg, K., J. Am. Chem. Soc., 1982, 104,697-704.(b) Bruno, G.; Rotondo, E.; Giordano, G.; Schiavo, S. L.; Piraino, P.; Tresoldi, G., Inog. Chim. Acta., 1993, 208, 67-75 李堅呈, 碩士論文, 中興大學化學研究所 Braunstein, P., J. Organomet. Chem., 2004, 689, 3953–3967
Alkynylphosphines Me2NCH2C≡CPR2 (2a: R = tBu; 2b: R = Ph) were prepared according to the procedures modified from published methods. Further treatment of a dppm-bridged dicobalt compound [Co2(CO)6(μ-P,P-PPh2CH2PPh2)] 3 with one molar equivalent of 2 in toluene at 110˚C afforded alkyne-bridged dicobalt phosphines [(μ-PPh2CH2PPh2)Co2(CO)4(μ,η-Me2NCH2C≡CPR2)] (4a: R = tBu; 4b: R = Ph). A smaller amount of oxidized counterpart [(μ-PPh2CH2PPh2)Co2(CO)4(μ,η-Me2NCH2C≡CP(=O)(t-Bu)2)] 4aO was obtained during the chromatographic process of 4a. Compound 4b and 4aO were characterized by spectroscopic methods as well as single-crystal X-ray diffraction. Both 4a and 4b are authentic cobalt-containing P∩N bidentate ligands and can be used in ligating palladium sources such as Pd(OAc)2 or PdCl2. Reasonable efficiencies were observed for Amination reactions of arylbromides and morpholine employing 4a- or 4b-chelated palladium complex as the catalytic precursor.
其他識別: U0005-0707200714194800
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