Chinese Journal of Organic Chemistry >
CsOH/DMSO Promoted Reactions of Aryl Halides with Phenols: A Convenient Method for the Synthesis of Diaryl Ethers
Received date: 2013-10-16
Revised date: 2013-11-18
Online published: 2013-11-25
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21073132, 20902070).
The reactions of aryl halides with phenols promoted by CsOH/dimethyl sulfoxide (CsOH/DMSO) led to diaryl ethers. This method was free of transition metal catalysts and ligands, and could be performed without inert gas protection. Therefore, it was a concise and green synthetic method. Based on the experimental results, a mechanism involving the benzyne intermediates is supposed.
Key words： aryl halides; phenols; diaryl ethers; CsOH; dimethyl sulfoxide (DMSO); benzyne
Chen Pingliang , Lu Shijie , Hu Xingen , Xu Qing . CsOH/DMSO Promoted Reactions of Aryl Halides with Phenols: A Convenient Method for the Synthesis of Diaryl Ethers[J]. Chinese Journal of Organic Chemistry, 2014 , 34(1) : 112 -117 . DOI: 10.6023/cjoc201310021
[1] (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
(b) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
(c) Hartwig, J. F. Nature 2008, 455, 314.
(d) Enthaler, S.; Company, A. Chem. Soc. Rev. 2011, 40, 4912.
(e) Yang, J.; Zhang, L.; Jin, X.; Gao, H.; Fang, J.; Li, R.; Fang, Y. Chin. J. Org. Chem. 2013, 33, 1647 (in Chinese).
(杨建平, 张莉, 金小平, 高浩其, 房江华, 李瑞丰, 方烨汶, 有机化学, 2013, 33, 1647.)
[2] (a) Theil, F. Angew. Chem., Int. Ed. 1999, 38, 2345.
(b) Sawyer, J. S. Tetrahedron 2000, 56, 5045.
(c) Pitsinos, E. N.; Vidali, V. P.; Couladouros, E. A. Eur. J. Org. Chem. 2011, 1207.
(d) Zhu, J. Synlett 1997, 133.
(e) Bunnett, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273.
[3] (a) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
(b) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
(d) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450.
(e) Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054.
(f) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954.
[4] (a) Urgaonkar, S.; Verkade, J. G. Org. Lett. 2005, 7, 3319.
(b) Ueno, M.; Hori, C.; Suzawa, K.; Ebisawa, M.; Kondo, Y. Eur. J. Org. Chem. 2005, 1965.
(c) Ueno, M.; Yonemoto, M.; Hashimoto, M.; Wheatley, A. E. H.; Naka, H.; Kondo, Y. Chem. Commun. 2007, 2264.
(d) Lee, J.; Fuchter, M. J.; Williamson, R. M.; Leeke, G. A.; Bush, E. J.; McConvey, I. F.; Saubern, S.; Ryanc, J. H.; Holmes, A. B. Chem. Commun. 2008, 4780.
(e) Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith III, W. J. J. Org. Chem. 1998, 63, 6338.
(f) Li, F.; Wang, Q.; Ding, Z.; Tao, F. Org. Lett. 2003, 5, 2169.
(g) Khalilzadeh, M. A.; Hosseini, A.; Pilevar, A. Eur. J. Org. Chem. 2011, 1587.
[5] (a) For a recent review: Mehta, V. P.; Punji, B. RSC Adv. 2013, 3, 11957.
(b) Yuan, Y.; Thomé, I. Kim, S. H.; Chen, D.; Beyer, A.; Bonnamour, J.; Zuidema, E.; Chang, S.; Bolm, C. Adv. Synth. Catal. 2010, 252, 2892.
(c) Cano, R.; Ramón, D. J.; Yus, M. J. Org. Chem. 2011, 76, 654.
(d) Hintermann, L.; Masuo, R.; Suzuki, K. Org. Lett. 2008, 10, 4859.
(e) Barbero, N.; SanMartin, R.; Domínguez, E. Tetrahedron 2009, 65, 5729.
(f) Zhao, J.; Zhao, Y.; Fu, H. Angew. Chem., Int. Ed. 2011, 50, 3769.
(g) Zhao, J.; Zhao,Y.; Fu, H. Org. Lett. 2012, 14, 2710.
(h) Yang, S. L.; Wu, C. Q.; Ruan, M. B.; Yang, Y. Q.; Zhao, Y. X.; Niu, J. J.; Yang, W.; Xu, J. W. Tetrahedron Lett. 2012, 53, 4288.
(i) Kumar, A.; Bhakuni, B. S.; Prasad, C. D.; Kumar S.; Kumar, S. Tetrahedron 2013, 69, 5383.
[6] (a) Liu, Q.; Lu, Z.; Ren, W.; Shen, K.; Wang, Y.; Xu, Q. Chin. J. Chem. 2013, 31, 764.
(b) Liu, C.; Zang, X.; Yu, B.; Yu, X.; Xu, Q. Synlett 2011, 1143.
(c) Yu, X. C.; Li, B.; Yu, B. H.; Xu, Q. Chin. Chem. Lett. 2013, 24, 605.
[7] (a) Maligres, P. E.; Li, J.; Krska, S. W.; Schreier, J. D.; Raheem, I. T. Angew. Chem., Int. Ed. 2012, 51, 9071.
(b) Dash, P.; Janni, M.; Peruncheralathan, S. Eur. J. Org. Chem. 2012, 4914.
(c) Platon, M.; Cui, L.; Mom, S.; Richard, P.; Saeys, M.; Hierso, J. C. Adv. Synth. Catal. 2011, 353, 3403.
(d) Cherng, Y. J. Tetrahedron 2002, 58, 4931.
(e) Lanni, E. L.; Bosscher, M. A.; Ooms, B. D.; Shandro, C. A.; Ellsworth, B. A.; Anderson, C. E. J. Org. Chem. 2008, 73, 6425.
[8] (a) Dijkstra, G. W.; Kruizinga, H.; Kellogg, R. M. J. Org. Chem. 1987, 52, 4230.
(b) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000.
(c) Salvatore, R. N.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2002, 67, 674.
[9] Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2003, 42, 502.
[10] Senecal, T. D.; Parsons, A. T.; Buchwald, S. J. Org. Chem. 2011, 76, 1174.
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