Browse > Article
http://dx.doi.org/10.5012/bkcs.2013.34.12.3915

Aminophenols as Efficient Ligand for Copper-Catalyzed Ullmann-type Synthesis of Diaryl Ethers  

Qian, Cunwei (School of Chemistry and Chemical Engineering, Yancheng Teachers University)
Qin, Liang (School of Chemistry and Chemical Engineering, Yancheng Teachers University)
Zong, Qianshou (School of Biological and Chemical Engineering, Jiaxing University)
Wu, Lin (School of Chemistry and Chemical Engineering, Yancheng Teachers University)
Fang, Dong (School of Chemistry and Chemical Engineering, Yancheng Teachers University)
Publication Information
Keywords
Copper catalyst; Aminophenols; Ullmann coupling; Diaryl ethers;
Citations & Related Records
연도 인용수 순위
  • Reference
1 (a) Lindley, J. Tetrahedron 1984, 40, 1433.   DOI   ScienceOn
2 (b) Theil, F. Angew. Chem., Int. Ed. 1999, 38, 2345.   DOI   ScienceOn
3 (c) Sawyer, J. S. Tetrahedron 2000, 56, 5045.   DOI   ScienceOn
4 (d) Thomas, A. W.; Ley, S. V. Angew. Chem., Int. Ed. 2003, 42, 5400.   DOI   ScienceOn
5 (e) Kunz, K.; Scholz, U.; Ganzer, D. Synlett. 2003, 15, 2428.
6 (f) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.   DOI   ScienceOn
7 (a) Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909.   DOI
8 (b) Singh, S. B.; Pettit, G. R. J. Org. Chem. 1990, 55, 2797.   DOI
9 (c) Deshpande, V. E.; Gohkhale, N. J. Tetrahedron Lett. 1992, 33, 4213.   DOI   ScienceOn
10 (d) Evans, D. A.; DeViries, K. M. In Glycopeptide Antibiotics, Drugs and the Pharmaceutical Sciences; Nagarajan, R., Ed.; Marcel Decker: New York, 1994; pp 63-104.
11 (f) Cristau, P.; Vors, J.-P.; Zhu, J. Tetrahedron 2003, 59, 7859.   DOI   ScienceOn
12 (g) Qian, C.; Pang, Y.; Fang, D.; Zong, Q. Chinese Journal of Pesticide Science, 2013, 15(3), 44.
13 (a) Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 13109.   DOI   ScienceOn
14 (b) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333.   DOI   ScienceOn
15 (c) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395.   DOI   ScienceOn
16 (d) Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.   DOI   ScienceOn
17 (e) Mann, G.; Incarvito, C.; Rheigold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224.   DOI   ScienceOn
18 (f) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553.   DOI   ScienceOn
19 (g) Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.   DOI   ScienceOn
20 (h) Vorogushin, A. V.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 8146.   DOI   ScienceOn
21 (i) Burgos, C. H.; Barder, T. E.; Huang, X.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 4321.   DOI   ScienceOn
22 Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382.   DOI
23 Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539.   DOI   ScienceOn
24 Fagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A. J. Am. Chem. Soc. 2000, 122, 5043.   DOI   ScienceOn
25 Qian, C.; Xu, S.; Fang, D.; Zong, Q. Chin. J. Chem. 2012, 30, 1881.   DOI   ScienceOn
26 Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623.   DOI   ScienceOn
27 Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 3799.   DOI   ScienceOn
28 Cai, Q.; Zou, B.; Ma, D. Angew. Chem., Int. Ed. 2006, 45, 1276.   DOI   ScienceOn
29 Cai, Q.; He, G.; Ma, D. J. Org. Chem. 2006, 71, 5268.   DOI   ScienceOn
30 Ouali, A.; Spindler, J. F.; Cristau, H.-J.; Taillefer, M. Adv. Synth. Catal. 2006, 348, 499.   DOI   ScienceOn
31 Cristau, H. J.; Cellier, P. P.; Hamada, S.; Spindler, J. F.; Tailefer, M. Org. Lett. 2004, 6, 913.   DOI   ScienceOn
32 Rao, H.; Jin, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Chem.-Eur. J. 2006, 12, 3636.   DOI   ScienceOn
33 Palomo, C.; Oiarbide, M.; Lopez, R.; Gomez-Bengoa, E. Chem. Commun. 1998, 2091.
34 Lv, X.; Bao, W. J. Org. Chem. 2007, 72, 3863.   DOI   ScienceOn
35 Naidu, A. B.; Raghunath, O. R.; Prasad, D. J. C.; Sekar, G. Tetrahedron Lett. 2008, 49, 1057.   DOI   ScienceOn
36 Chen, Y.; Chen, H. Org. Lett. 2006, 8, 5609.   DOI   ScienceOn
37 Miao, T.; Wang, L. Tetrahedron Lett. 2007, 48, 95.   DOI   ScienceOn
38 Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937.   DOI   ScienceOn
39 Zhao, Y.; Wang, Y.; Sun, H.; Li, L.; Zhang, H. Chem. Commun. 2007, 3186.
40 Zhang, Q.; Wang, D.; Wang, X.; Ding, K. J. Org. Chem. 2009, 74, 7187.   DOI   ScienceOn
41 Chang, J. W. W.; Chee, S.; Maka, S.; Buranaprasertsuk, P.; Chavasiri, W.; Chan, P. W. H. Tetrahedron Lett. 2008, 49, 1018.
42 Maiti, D.; Buchwald, S. L. J. Org. Chem. 2010, 75, 1791.   DOI   ScienceOn
43 Qian, C.; Zong, Q.; Fang, D. Chin. J. Chem. 2012, 30, 199.   DOI   ScienceOn
44 Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315.   DOI   ScienceOn
45 Gujadhur, R. K.; Venkataraman, D. Synth. Commun. 2001, 31, 2865.   DOI   ScienceOn
46 Niu, J.; Zhou, H.; Li, Z.; Xu, J.; Hu, S. J. Org. Chem. 2008, 73, 7814.   DOI   ScienceOn
47 (a) Cameron, P. A.; Gibson, V. C.; Redshaw, C.; Segal, J. A.; White, A. J. P.; Williams, D. J. Dalton Trans. 2002, 415.
48 (b) Oakes, D. C. H.; Kimberley, B. S.; Gibson, V. C.; Jones, D. J.; White, A. J. P.; Williams, D. J. Chem. Commun. 2004, 2174.
49 (c) Oakes, D. C. H.; Gibson, V. C.; White, A. J. P.; Williams, D. J. Inorg. Chem. 2006, 45, 3477.
50 (d) Nimitsiriwat, N.; Gibson, V. C.; Marshall, E. L.; Elsegood, M. R. J. Inorg. Chem. 2008, 47, 5417.   DOI   ScienceOn
51 (e) Nimitsiriwat, N.; Marshall, E. L.; Gibson, V. C.; Elsegood, M. R. J.; Dale, S. H. J. Am. Chem. Soc. 2004, 126, 13598.   DOI   ScienceOn
52 (f) Nimitsiriwat, N.; Gibson, V. C.; Marshall, E. L.; Elsegood, M. R. J. Dalton Trans. 2009, 3710.
53 (g) Meppelder, G. J. M.; Fan, H. T.; Spaniol, T. P.; Okuda, J. Inorg. Chem. 2009, 48, 7378.   DOI   ScienceOn
54 (h) Douglas, A. F.; Patrick, B. O.; Mehrkhodavandi, P. Angew. Chem., Int. Ed. 2008, 47, 2290.   DOI   ScienceOn
55 (a) Tang, Z.; Chang, S.; Zhang, C.; Yan, L.; Liu, H. Huazhong Shifan Daxue Xuebao, ZiranKexueban, 2011, 45(1), 63.
56 (i) Wang, X. K.; Chen, Z.; Sun, X. L.; Tang, Y.; Xie, Z. W. Org. Lett. 2011, 13, 4758.   DOI   ScienceOn
57 (j) Zhang, J.; Qiu, J.; Yao, Y.; Zhang, Y.; Wang, Y.; Shen, Q. Organometallics 2012, 31, 3138.   DOI   ScienceOn
58 (k) Lu, M.; Yao, Y. M.; Zhang, Y.; Shen, Q. Dalton Trans. 2010, 39, 9530.   DOI   ScienceOn
59 (b) Tang, Z.; Chen, W.; Zhu, Z.; Liu, Z. J. Heterocyclic Chem. 2011, 48, 255.   DOI
60 (e) Zenitani, S.; Tashiro, S.; Shindo, K.; Nagai, K.; Suzuki, K.; Imoto, M. J. Antibiot. 2003, 56, 617.   DOI