Methenamine as an Efficient Ligand for Copper-catalyzed Coupling of Phenols with Aryl Halides
Corresponding Author
Cunwei Qian
School of Chemistry and Chemical Engineering, Yancheng Teachers University, Yancheng, Jiangsu 224051, China
School of Chemistry and Chemical Engineering, Yancheng Teachers University, Yancheng, Jiangsu 224051, China, Tel.: 18962033519; Fax: 0086-0515-88233188Search for more papers by this authorQianshou Zong
School of Biological and Chemical Engineering, Jiaxing University, Jiaxing, Zhejiang 314001, China
Search for more papers by this authorDong Fang
School of Chemistry and Chemical Engineering, Yancheng Teachers University, Yancheng, Jiangsu 224051, China
Search for more papers by this authorCorresponding Author
Cunwei Qian
School of Chemistry and Chemical Engineering, Yancheng Teachers University, Yancheng, Jiangsu 224051, China
School of Chemistry and Chemical Engineering, Yancheng Teachers University, Yancheng, Jiangsu 224051, China, Tel.: 18962033519; Fax: 0086-0515-88233188Search for more papers by this authorQianshou Zong
School of Biological and Chemical Engineering, Jiaxing University, Jiaxing, Zhejiang 314001, China
Search for more papers by this authorDong Fang
School of Chemistry and Chemical Engineering, Yancheng Teachers University, Yancheng, Jiangsu 224051, China
Search for more papers by this authorAbstract
Employing methenamine as a new supporting ligand, the copper-catalyzed coupling reactions of aryl bromides or aryl iodides with various phenols successfully proceeded in good yields under mild conditions. A series of diaryl ethers were obtained with excellent yields in the presence of K3PO4 and copper(I) salt.
REFERENCES
- 1For reviews, see:
- 1a Lindley, J.. Tetrahedron, 1984, 40, 1433.
- 1b
Theil, F..
Angew. Chem., Int. Ed.,
1999,
38,
2345.
10.1002/(SICI)1521-3773(19990816)38:16<2345::AID-ANIE2345>3.0.CO;2-5 CAS PubMed Web of Science® Google Scholar
- 1c Sawyer, J. S.. Tetrahedron, 2000, 56, 5045.
- 1d Thomas, A. W.; Ley, S. V.. Angew. Chem., Int. Ed., 2003, 42, 5400.
- 1e Kunz, K.; Scholz, U.; Ganzer, D.. Synlett, 2003, 15, 2428.
- 1f Beletskaya, I. P.; Cheprakov, A. V.. Coord. Chem. Rev., 2004, 248, 2337.
- 1g Monnier, F.; Taillefer, M.. Angew. Chem., Int. Ed., 2008, 47, 3096.
- 2For selected examples of medicinally important diaryl ethers, see:
- 2a Jung, M. E.; Rohloff, J. C.. J. Org. Chem., 1985, 50, 4909.
- 2b Singh, S. B.; Pettit, G. R.. J. Org. Chem., 1990, 55, 2797.
- 2c Deshpande, V. E.; Gohkhale, N. J.. Tetrahedron Lett., 1992, 33, 4213.
- 2d Evans, D. A.; DeViries, K. M.. In Glycopeptide Antibiotics, Drugs and the Pharmaceutical Sciences, Ed.: R. Nagarajan, Marcel Decker, New York, 1994, pp. 63–104.
- 2e Zenitani, S.; Tashiro, S.; Shindo, K.; Nagai, K.; Suzuki, K.; Imoto, M.. J. Antibiot., 2003, 56, 617.
- 2f Cristau, P.; Vors, J.-P.; Zhu, J.. Tetrahedron, 2003, 59, 7859.
- 3For selected examples of Pd-catalyzed C-O coupling reactions, see:
- 3a Mann, G.; Hartwig, J. F.. J. Am. Chem. Soc., 1996, 118, 13109.
- 3b Palucki, M.; Wolfe, J. P.; Buchwald, S. L.. J. Am. Chem. Soc., 1996, 118, 10333.
- 3c Palucki, M.; Wolfe, J. P.; Buchwald, S. L.. J. Am. Chem. Soc., 1997, 119, 3395.
- 3d Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L.. J. Am. Chem. Soc., 1999, 121, 4369.
- 3e Mann, G.; Incarvito, C.; Rheigold, A. L.; Hartwig, J. F.. J. Am. Chem. Soc., 1999, 121, 3224.
- 3f Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F.. J. Org. Chem., 2002, 67, 5553.
- 3g Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B.. Tetrahedron, 2002, 58, 2041.
- 3h Vorogushin, A. V.; Huang, X.; Buchwald, S. L.. J. Am. Chem. Soc., 2005, 127, 8146.
- 3i Burgos, C. H.; Barder, T. E.; Huang, X.; Buchwald, S. L.. Angew. Chem., Int. Ed., 2006, 45, 4321.
- 4 Ullmann, F.. Ber. Dtsch. Chem Ges., 1903, 36, 2382.
- 5For selected examples of Cu-catalyzed C-O coupling reactions, see:
- 5a Marcoux, J.-F.; Doye, S.; Buchwald, S. L.. J. Am. Chem. Soc., 1997, 119, 10539.
- 5b Fagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A.. J. Am. Chem. Soc., 2000, 122, 5043.
- 5c Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J.. Org. Lett., 2002, 4, 1623.
- 5d Ma, D.; Cai, Q.; Zhang, H.. Org. Lett., 2003, 5, 3799.
- 5e Cai, Q.; Zou, B.; Ma, D.. Angew. Chem., Int. Ed., 2006, 45, 1276.
- 5f Cai, Q.; He, G.; Ma, D.. J. Org. Chem., 2006, 71, 5268.
- 5g Ouali, A.; Spindler, J. F.; Cristau, H.-J.; Taillefer, M.. Adv. Synth. Catal., 2006, 348, 499.
- 5h Cristau, H. J.; Cellier, P. P.; Hamada, S.; Spindler, J. F.; Tailefer, M.. Org. Lett., 2004, 6, 913.
- 5i Rao, H.; Jin, Y.; Fu, H.; Jiang, Y.; Zhao, Y.. Chem.-Eur. J., 2006, 12, 3636.
- 5j Palomo, C.; Oiarbide, M.; Lopez, R.; Gomez-Bengoa, E.. Chem. Commun., 1998, 2091.
- 5k Lv, X.; Bao, W.. J. Org. Chem., 2007, 72, 3863.
- 5l Naidu, A. B.; Raghunath, O. R.; Prasad, D. J. C.; Sekar, G.. Tetrahedron Lett., 2008, 49, 1057.
- 5m Chen, Y.; Chen, H.. Org. Lett., 2006, 8, 5609.
- 5n Miao, T.; Wang, L.. Tetrahedron Lett., 2007, 48, 95.
- 5o Evans, D. A.; Katz, J. L.; West, T. R.. Tetrahedron Lett., 1998, 39, 2937.
- 5p Zhao, Y.; Wang, Y.; Sun, H.; Li, L.; Zhang, H.. Chem. Commun., 2007, 3186.
- 5q Zhang, Q.; Wang, D.; Wang, X.; Ding, K.. J. Org. Chem., 2009, 74, 7187.
- 5r Chang, J. W. W.; Chee, S.; Maka, S.; Buranaprasertsuk, P.; Chavasiri, W.; Chan, P. W. H.. Tetrahedron Lett., 2008, 49, 1018.
- 5s Maiti, D.; Buchwald, S. L.. J. Org. Chem., 2010, 75, 1791.
- 5t Gujadhur, R. K.; Bates, C. G.; Venkataraman, D.. Org. Lett., 2001, 3, 4315.
- 5u Gujadhur, R. K.; Venkataraman, D.. Synth. Commun., 2001, 31, 2865.
- 5v Niu, J.; Zhou, H.; Li, Z.; Xu, J.; Hu, S.. J. Org. Chem., 2008, 73, 7814.
- 6 Tenne, R.. Angew. Chem., Int. Ed., 2003, 42, 5124.
- 7a Kim, G. -S.; Ansari, S. G.; Seo, H.-K.; Kim, Y.-S.; Yang, O.-B.; Shin, H.-S.. Appl. Surf. Sci., 2007, 253, 7197.
- 7b Wang, H.; Liang, J.; Fan, H.; Xi, B.; Zhang, M.; Xiong, S.; Zhu, Y.; Qian, Y.. J. Solid State Chem., 2008, 181, 122.
- 7c Lang, J.; Han, Q.; Li, C.; Yang, J.; Li, X.; Yang, L.; Wang, D.; Zhai, H.; Gao, M.; Zhang, Y.; Liu, X.; Wei, M.. Appl. Surf. Sci., 2010, 256, 3365.
- 7d Chao, C.; Chan, C.; Huang, J.; Chang, L.; Shih, H.. Curr. Appl. Phys., 2011, 11, 5136.
- 8a Altman, R. A.; Buchwald, S. L.. Org. Lett., 2007, 9, 643.
- 8b Mederski, W. W. K. K. R.; Lefort, M.; Germann, M.; Kux, D.. Tetrahedron, 1999, 55, 12757.
- 8c Lam, Y. S. P.; Clark, C. G.; Sauber, S.; Adams, J.; Averill, K. M.; Chan, D. M. T.; Combs, A.. Synlett, 2000, 674.
- 9 Liu, Z. J.; Larock, R. C.. J. Org. Chem., 2006, 71, 3198.