European Journal of Chemistry

Recyclable and reusable nano-CuFe2O4 catalyzed C-O cross-coupling



Main Article Content

Venkanna Avudoddi
Vinod Kumar Goud Palle
Venkateshwar Rao Pallapothula

Abstract

An efficient protocol was developed and validated for the synthesis of biaryl/aryl alkyl ethers using CuFe2O4 nano powder as a recyclable catalyst via the reaction between aryl halides and phenols/alcohols. Variety of aryl ethers were synthesized efficiently in the presence of catalytic amount of CuFe2O4, KOH as base, under ligand free conditions in nitrogen atmosphere with DMSO as solvent at 120 oC. The catalyst is air-stable, inexpensive, magnetically separable and recyclable up to four cycles.

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Avudoddi, V.; Palle, V. K. G.; Pallapothula, V. R. Recyclable and Reusable Nano-CuFe2O4 Catalyzed C-O Cross-Coupling. Eur. J. Chem. 2012, 3, 298-304.

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References

[1]. Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054-3131.
http://dx.doi.org/10.1021/cr8002505
PMid:18698737

[2]. Theil, F. Angew. Chem. Int. Ed. 1999, 38, 2345-2347.
http://dx.doi.org/10.1002/(SICI)1521-3773(19990816)38:16<2345::AID-ANIE2345>3.0.CO;2-5

[3]. Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8556.
http://dx.doi.org/10.1021/ja00098a015

[4]. Asano, M.; Inoue, M.; Katoh, T. Synlett 2005, 2599-2602.

[5]. Jiang, H.; Leger, J. -M.; Huc, I. J. Am. Chem. Soc. 2003, 125, 3448-3449.
http://dx.doi.org/10.1021/ja029887k
PMid:12643704

[6]. Yamazaki, N.; Washio, I.; Shibasaki, Y.; Ueda, M. Org. Lett. 2006, 8, 2321-2324.
http://dx.doi.org/10.1021/ol0605880
PMid:16706516

[7]. Bolm, C.; Hildebrand, J. P.; Muniz, Hermanns, K, N. Angew. Chem. Int. Ed. 2001, 40, 3284-3308.
http://dx.doi.org/10.1002/1521-3773(20010917)40:18<3284::AID-ANIE3284>3.0.CO;2-U

[8]. Matsumoto, Y.; Uchida, W.; Nakahara, H.; Yanagisawa, I.; Shibanuma, T.; Nohira, H. Chem. Pharm. Bull. 2000, 48, 428-432.
http://dx.doi.org/10.1248/cpb.48.428

[9]. Gu, W. X.; Jing, X. B.; Pan, X. F.; Chan, A. S. C.; Yang, T. K. Tetrahedron Lett. 2000, 41, 6079-6082.
http://dx.doi.org/10.1016/S0040-4039(00)00820-0

[10]. Goodbrand, H. B.; Hu, N. -X. J. Org. Chem. 1999, 64, 670-674.
http://dx.doi.org/10.1021/jo981804o

[11]. Ullmann, F. Chem. Ber. 1904, 37, 853-854.
http://dx.doi.org/10.1002/cber.190403701141

[12]. Sawyer, J. S. Tetrahedron 2000, 56, 5045-5065.
http://dx.doi.org/10.1016/S0040-4020(00)00257-X

[13]. Mann, G.; Hartwig, J. F. Tetrahedron Lett. 1997, 38, 8005-8008.
http://dx.doi.org/10.1016/S0040-4039(97)10175-7

[14]. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369-4378.
http://dx.doi.org/10.1021/ja990324r

[15]. Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395-3396.
http://dx.doi.org/10.1021/ja9640152

[16]. Prim, D.; Campagne, J. M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041-2075.
http://dx.doi.org/10.1016/S0040-4020(02)00076-5

[17]. Kataoka, N.; Shelby, Q.; Stambuli, J.; Hartwig, J. J. Org. Chem. 2002, 67, 5553-5556.
http://dx.doi.org/10.1021/jo025732j
PMid:12153253

[18]. Vorogushin, A. V.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 8146-8149.
http://dx.doi.org/10.1021/ja050471r
PMid:15926842

[19]. Burgos, C. H.; Barder, T. E.; Huang, X.; Buchwald, S. L. Angew. Chem. Int. Ed. 2006, 45, 4321-4326.
http://dx.doi.org/10.1002/anie.200601253
PMid:16733839

[20]. Mann, G.; Hartwig, J. F. Tetrahedron Lett. 1997, 38, 8005-8008.
http://dx.doi.org/10.1016/S0040-4039(97)10175-7

[21]. Vorogushin, A. V.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 8146-8149.
http://dx.doi.org/10.1021/ja050471r
PMid:15926842

[22]. Prim, D.; Campagne, J. M.; Joseph, D.; Andrioletti, B. Tetrahedron. 2002, 58, 2041-2075.
http://dx.doi.org/10.1016/S0040-4020(02)00076-5

[23]. Palomo, C.; Oiarbide, M.; LIpez, R.; Bengoa, E. G. Chem. Commun. 1998, 2091-2092.
http://dx.doi.org/10.1039/a805783d

[24]. Cristau, H. J.; Cellier, P. P.; Hamada, S.; Spindler, J. -F.; Taillefer, M. Org. Lett. 2004, 6, 913-916.
http://dx.doi.org/10.1021/ol036290g
PMid:15012063

[25]. Chen, Y. -J.; Chen, H. -H. Org. Lett. 2006, 8, 5609-5612.
http://dx.doi.org/10.1021/ol062339h
PMid:17107084

[26]. Rao, H.; Jin, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Chem. Eur. J. 2006, 12, 3636-3646.
http://dx.doi.org/10.1002/chem.200501473
PMid:16485315

[27]. Cai, Q.; Zou, B.; Ma, D. Angew. Chem. Int. Ed. 2006, 45, 1276-1279.
http://dx.doi.org/10.1002/anie.200503538
PMid:16425327

[28]. Altman, R. A.; Buchwald, S. L. Org. Lett. 2007, 9, 643-646.
http://dx.doi.org/10.1021/ol062904g
PMid:17286371

[29]. Ouali, A.; Spindler, J.-F.; Jutand, A.; Taillefer, M. Adv. Synth. Catal. 2007, 349, 1906-1916.
http://dx.doi.org/10.1002/adsc.200600628

[30]. Ullmann, F. Ber. Dtsch. Chem Ges. 1903, 36, 2382-2384.
http://dx.doi.org/10.1002/cber.190303602174

[31]. Jin, Y.; Liu, J.; Yin, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Synlett, 2006, 1564-1568.

[32]. Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315-4317.
http://dx.doi.org/10.1021/ol0170105
PMid:11784206

[33]. Chen, Y. J.; Chen, H. H. Org. Lett. 2006, 8, 5609-5612.
http://dx.doi.org/10.1021/ol062339h
PMid:17107084

[34]. Weingarten, H. J. Org. Chem. 1964, 29, 3624-3626.
http://dx.doi.org/10.1021/jo01035a046

[35]. Marcoux, J. F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539-10540.
http://dx.doi.org/10.1021/ja971901j

[36]. Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623-1626.
http://dx.doi.org/10.1021/ol025839t
PMid:11975644

[37]. Lv, X.; Bao, W. J. Org. Chem. 2007, 72, 3863-3867.
http://dx.doi.org/10.1021/jo070443m
PMid:17432916

[38]. Gujadhur, R. K.; Venkataraman, D. Synth. Commun. 2001, 31, 2865-2879.
http://dx.doi.org/10.1081/SCC-100105338

[39]. Zhang, Q.; Wang, D.; Wang, X.; Ding, K. J. Org. Chem. 2009, 74, 7187-7190.
http://dx.doi.org/10.1021/jo9012157
PMid:19673481

[40]. Kiyomori, A.; Marcoux, J. F.; Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2657-2660.
http://dx.doi.org/10.1016/S0040-4039(99)00291-9

[41]. Ma, D.; Cai, Q. Org. Lett. 2003, 5, 3779-3782.
http://dx.doi.org/10.1021/ol035323p
PMid:14535708

[42]. Kim, J. Y.; Park, J. C.; Kim, A.; Kim, A. Y.; Lee, H. J.; Song, H.; Park, K. H. Eur. J. Inorg. Chem. 2009, 4219-4223.
http://dx.doi.org/10.1002/ejic.200900730

[43]. Larsson, P. F.; Correa, A.; Carril, M.; Norrby, P. O.; Bolm, C. Angew. Chem. Int. Ed. 2009, 48, 5691-5693.
http://dx.doi.org/10.1002/anie.200902236
PMid:19554589

[44]. Liu, Z.; Larock, R. C. J. Org. Chem. 2006, 71, 3198-3209.
http://dx.doi.org/10.1021/jo0602221
PMid:16599619 PMCid:2627407

[45]. Paul, S.; Gupta, M. Tetrahedron Lett. 2004, 45, 8825-8829.
http://dx.doi.org/10.1016/j.tetlet.2004.10.009

[46]. Xu, L. W.; Xia, C. G.; Li, J. W.; Hu, X. X. Synlett. 2003, 2071-2073.

[47]. Mao, J.; Xie, G.; Wu, M.; Guo, J.; Ji, S. Adv. Synth. Catal. 2008, 350, 2477-2482.
http://dx.doi.org/10.1002/adsc.200800517

[48]. Bistri, O.; Correa, A.; Bolm, C. Angew. Chem. Int. Ed. 2008, 47, 586-588.
http://dx.doi.org/10.1002/anie.200704018
PMid:18058877

[49]. Ouali, A.; Spindler, J. F.; Cristau, H. J.; Taillefer, M. Adv. Synth. Catal. 2006, 348, 499-505.
http://dx.doi.org/10.1002/adsc.200505385

[50]. Naidu, A. B.; Raghunath, O. R.; Prasad, D. J. C.; Sekar, G. Tetrahedron Lett. 2008, 49, 1057-1061.
http://dx.doi.org/10.1016/j.tetlet.2007.11.203

[51]. Naidu, A. B.; Jaseer, E. A.; Sekar, G. J. Org. Chem. 2009, 74, 3675-3679.
http://dx.doi.org/10.1021/jo900438e
PMid:19361190

[52]. Lipshutz, B. H.; Unger, J. B.; Taft, B. R. Org. Lett. 2007, 9, 1089-1092.
http://dx.doi.org/10.1021/ol0700409
PMid:17305352

[53]. Swapna, K.; Murthy, S. N.; Nageswar, Y. V. D. Eur. J. Org. Chem. 2011, 1940-1946.
http://dx.doi.org/10.1002/ejoc.201001639

[54]. Knight, W. D.; Clemenger, K.; de Heer, W. A.; Saunders, W. A. M.; Chou, Y.; Cohen, M. L. Phys. Rev. Lett. 1984, 52, 2141-2143.
http://dx.doi.org/10.1103/PhysRevLett.52.2141

[55]. Pacchioni, G. Surf. Rev. Lett. 2000, 7, 277-306.

[56]. Kidwai, M.; Mishra, N. K.; Bansal, V.; Kumar, A.; Mozumdar, S. Tetrahedron Lett. 2007, 48, 8883-8887.
http://dx.doi.org/10.1016/j.tetlet.2007.10.050

[57]. Jammi, S.; Sakthivel, S.; Rout, L.; Mukherjee, T.; Mandal, S.; Mitra, R.; Saha, P.; Punniamurthy, T. J. Org. Chem. 2009, 74, 1971-1976.
http://dx.doi.org/10.1021/jo8024253
PMid:19173559

[58]. Sreedhar, B.; Arundhathi, R.; Reddy, P. L.; Kantam, M. L. J. Org. Chem. 2009, 74, 7951-7954.
http://dx.doi.org/10.1021/jo901462g
PMid:19772325

[59]. Tasca, J. E.; Ponzinibbio, A.; Diaz, G.; Bravo, R. D.; Lavat, A.; Gonzalez, M. G. Top Catal. 2010, 53, 1087-1090.
http://dx.doi.org/10.1007/s11244-010-9538-0

[60]. Bhadra, S.; Sreedhar, B.; Ranu, B. C. Adv. Synth. Catal. 2009, 351, 2369-2378.
http://dx.doi.org/10.1002/adsc.200900358

[61]. Maity, D.; Kale, S. N.; Ghanekar, R. K.; Xue, J. M.; Ding, J. J. Magn. Magn. Mater. 2009, 321, 3093-3098.
http://dx.doi.org/10.1016/j.jmmm.2009.05.020

[62]. Kantam, M. L.; Arundhathi, R.; Likhar, P. R.; Damodara, D. Adv. Synth. Catal. 2009, 351, 2633-2637.
http://dx.doi.org/10.1002/adsc.200900405

[63]. Hunter, D. H.; Cram, D. J. J. Am. Chem. Soc. 1966, 88, 5765-5776.
http://dx.doi.org/10.1021/ja00976a018

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