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Several supporting ligands have been introduced to achieve a high efficiency of Ullmann coupling under mild reaction conditions, among them: (a) N,N-Diethylsalicylamide: Kwong, F. Y, Buchwald, S. L. Org. Lett. 2003, 5, 793-796
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Several supporting ligands have been introduced to achieve a high efficiency of Ullmann coupling under mild reaction conditions, among them: (a) N,N-Diethylsalicylamide: Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793-796.
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β-Diketone: Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742-8743.
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(b) β-Diketone: Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742-8743.
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34547621822
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2-Hydroxybenzaldehyde N-phenylhydrazone: Jiang, Q.; Jiang, D.; Jiang, Y.; Zhao, Y. Synlett 2007, 1836-1842.
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(d) 2-Hydroxybenzaldehyde N-phenylhydrazone: Jiang, Q.; Jiang, D.; Jiang, Y.; Zhao, Y. Synlett 2007, 1836-1842.
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N-Hydroxyimide: Ma, H.-C.; Jiang, X.-Z. J. Org. Chem. 2007, 72, 8943-8946.
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(e) N-Hydroxyimide: Ma, H.-C.; Jiang, X.-Z. J. Org. Chem. 2007, 72, 8943-8946.
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Hyppuric acid : Mao, J.; Guo, J.; Song, H.; Ji, S.-J. Tetrahedron 2008, 64, 1383-1387.
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(f) Hyppuric acid : Mao, J.; Guo, J.; Song, H.; Ji, S.-J. Tetrahedron 2008, 64, 1383-1387.
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Glyoxale bis hydrazone: Mino, T.; Harada, Y.; Shindo, H.; Sakamoto, M.; Fujita, T. Synlett 2008, 614-620.
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(g) Glyoxale bis hydrazone: Mino, T.; Harada, Y.; Shindo, H.; Sakamoto, M.; Fujita, T. Synlett 2008, 614-620.
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34
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0141854366
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Amino acids: Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453-2455.
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(h) Amino acids: Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453-2455.
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Amino acids: Cai, Q.; Zhu, W.; Zhang, H.; Zhang, Y. D.; Ma, D. W. Synthesis 2005, 496-499.
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(i) Amino acids: Cai, Q.; Zhu, W.; Zhang, H.; Zhang, Y. D.; Ma, D. W. Synthesis 2005, 496-499.
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44949217894
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N,N-Dimethylaminoethanol: Twieg, H., Jr.; R., J.; Lu, Z. K.; Huang, S. P. D. Tetrahedron Lett. 2003, 2453-2455.
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(j) N,N-Dimethylaminoethanol: Twieg, H., Jr.; R., J.; Lu, Z. K.; Huang, S. P. D. Tetrahedron Lett. 2003, 2453-2455.
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Ethylene glycol: Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581-584.
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(k) Ethylene glycol: Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581-584.
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1,10-Phenantroline: Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315-4317.
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(l) 1,10-Phenantroline: Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315-4317.
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39
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28044443893
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8-Hydroxyquinoline : Liu, L.; Frohn, M.; Domingueez, C.; Hungate, R.; Reider, P. J. J. Org. Chem. 2005, 70, 10135-10138.
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(m) 8-Hydroxyquinoline : Liu, L.; Frohn, M.; Domingueez, C.; Hungate, R.; Reider, P. J. J. Org. Chem. 2005, 70, 10135-10138.
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1,2-Diamines : Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
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(n) 1,2-Diamines : Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
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rac-1,1′-Binaphthol : Jiang, D.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2007, 72, 672-674.
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(o) rac-1,1′-Binaphthol : Jiang, D.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2007, 72, 672-674.
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34247615187
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Pyrroles: Pan, Y.; Lu, H.; Fang, Y.; Chen, L.; Qian, J.; Wang, J.; Li, C. Synthesis 2007, 1242-1246.
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(a) Pyrroles: Pan, Y.; Lu, H.; Fang, Y.; Chen, L.; Qian, J.; Wang, J.; Li, C. Synthesis 2007, 1242-1246.
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43
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44949195275
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Pyrrolo[2,3-c]pyridine, see ref 5f
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(b) Pyrrolo[2,3-c]pyridine, see ref 5f.
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1-Aryl-1H-indazoles : Liu, R.; Zhu, Y.; Qin, L.; Ji, S. Synth. Commun. 2008, 38, 249-254.
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(c) 1-Aryl-1H-indazoles : Liu, R.; Zhu, Y.; Qin, L.; Ji, S. Synth. Commun. 2008, 38, 249-254.
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35548992379
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2-Aryl-2H-indazoles : Liu, R.; Zhu, Y.; Qin, L.; Ji, S.; Katayama, H. Heterocycles 2007, 71, 1755-1763.
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(d) 2-Aryl-2H-indazoles : Liu, R.; Zhu, Y.; Qin, L.; Ji, S.; Katayama, H. Heterocycles 2007, 71, 1755-1763.
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46
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44949143416
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Oxindoles: ref 5d
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(e) Oxindoles: ref 5d.
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33845273049
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β-Lactams: Lu, H.; Li, C. Org. Lett. 2006, 8, 5365-5367.
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(f) β-Lactams: Lu, H.; Li, C. Org. Lett. 2006, 8, 5365-5367.
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48
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19544380068
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Other lactams: Hu, T.; Li, C. Org. Lett. 2005, 7, 2035-2038.
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(g) Other lactams: Hu, T.; Li, C. Org. Lett. 2005, 7, 2035-2038.
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0036170254
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Indolines: Yamada, K.; Kubo, T.; Tokuyama, H.; Fukuyama, T. Synlett 2002, 231-234.
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(h) Indolines: Yamada, K.; Kubo, T.; Tokuyama, H.; Fukuyama, T. Synlett 2002, 231-234.
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(i) 2-Aminobenzimidazoles: Evindar, G.; Batey, R. A. Org. Lett. 2003, 5, 133-136.
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36148978880
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For examples of related Pd-catalyzed N-anulation routes to indoles, see: (a) Fletcher, A. J, Bax, M. N, Willis, M. C. Chem. Commun. 2007, 4764-4766
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For examples of related Pd-catalyzed N-anulation routes to indoles, see: (a) Fletcher, A. J.; Bax, M. N.; Willis, M. C. Chem. Commun. 2007, 4764-4766.
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For examples, see: (a) Reference 2b.
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For examples, see: (a) Reference 2b.
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55
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21144450350
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(b) Hopkins, C. R.; Czekaj, M.; Kaye, S. S.; Gao, Z.; Pribish, J.; Pauls, H.; Liang, G.; Sides, K.; Cramer, D.; Cairns, J.; Luo, Y.; Lim, H.-K.; Vaz, R.; Rebello, S.; Maignan, S.; Dupuy, A.; Mathieu, M.; Levell, J. Bioorg. Med. Chem. Lett. 2005, 15, 2734-2737.
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Luo, Y.11
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56
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and references therein
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(c) Söderberg, B. C. G.; Banini, S. R.; Turner, M. R.; Minier, A. R.; Arrington, A. K. Synthesis 2008, 903-912, and references therein.
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Söderberg, B.C.G.1
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44949146611
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For recent reports on the synthesis of indole-3-carboxylic acid derivatives, see: (a) Reference 10c.
-
For recent reports on the synthesis of indole-3-carboxylic acid derivatives, see: (a) Reference 10c.
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59
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0037009958
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For an example of copper-catalyzed N-arylation of methyl indole-3-carboxylate, see: Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684-11688.
-
For an example of copper-catalyzed N-arylation of methyl indole-3-carboxylate, see: Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684-11688.
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60
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44949177863
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Beautement, K, Clough, J. M, Godfrey, C. R. A. EP. Patent 0307101. 1989. Chem. Abstr. 1989, 111, 114868
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Beautement, K.; Clough, J. M.; Godfrey, C. R. A. EP. Patent 0307101. 1989. Chem. Abstr. 1989, 111, 114868.
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61
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44949171070
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This result is consistent with the literature report on the preparation of N-tert-butyloxindole derivatives via Cu(I)-catalyzed intramolecular amidation, see ref 5d
-
This result is consistent with the literature report on the preparation of N-tert-butyloxindole derivatives via Cu(I)-catalyzed intramolecular amidation, see ref 5d.
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