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RETRACTED: Water-Soluble Copper Complex Catalyzed Solvent-Free Green Oxidation of Alkylarenes with tert-Butyl Hydroperoxide

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DOI: 10.4236/mrc.2013.22A006    3,729 Downloads   7,271 Views   Citations

ABSTRACT

The paper is withdrawn from "Modern Research in Catalysis" due to personal reasons from the corresponding author of this paper.

This article has been retracted to straighten the academic record. In making this decision the Editorial Board follows COPE's Retraction Guidelines. The aim is to promote the circulation of scientific research by offering an ideal research publication platform with due consideration of internationally accepted standards on publication ethics. The Editorial Board would like to extend its sincere apologies for any inconvenience this retraction may have caused.

Editor guiding this retraction: Anita LIU (Editorial Assistant of MRC)

The full retraction notice in PDF is preceding the original paper, which is marked "RETRACTED".

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The authors declare no conflicts of interest.

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References

[1] S. Nahm and S. M. Weinreb, “N-Methoxy-N-Methylamides as Effective Acylating Agents,” Tetrahedron Letters, Vol. 22, No. 39, 1981, pp. 3815-3818. doi:10.1016/S0040-4039(01)91316-4
[2] N. Kornblum and H. E. DeLaMare, “The Base Catalyzed Decomposition of a Dialkyl Peroxide,” Journal of The American Chemical Society, Vol. 73, No. 2, 1951, pp. 880-881. doi:10.1021/ja01146a542
[3] C. F. de Graauw, J. A. Peters, H. van Bekkum and J. Huskens, “Meerwein-Ponndorf-Verley Reductions and Oppenauer Oxidations: An Integrated Approach,” Synthesis, Vol. 1994, No. 10, 1994, pp. 1007-1017.
[4] R. A. Sheldon and J. K. Kochi, “Metal-Catalyzed Oxidations of Organic Compounds,” Academic Press, New York, 1981.
[5] M. Hudlicky, “Oxidations in Organic Chemistry,” American Chemical Society, Washington DC, 1990.
[6] G. Cainelli and G. Cardillo, “Chromium Oxidations in Organic Chemistry,” Springer, Berlin, 1984.
[7] J. Muzart, “Chromium-Catalyzed Oxidations in Organic Synthesis,” Chemical Reviews, Vol. 92, No. 1, 1992, pp. 113-140. doi:10.1021/cr00009a005
[8] J. Muzart, “Homogeneous CrVI-Catalyzed Benzylic, Allylic and Propargylic Oxidations by tert-Butyl Hydroperoxide,” Mini-Reviews in Organic Chemistry, Vol. 6, No. 1, 2009, pp. 9-20. doi:10.2174/157019309787316120
[9] B. M. Choudary, A. D. Prasad, V. Bhuma and V. Swapna, “Chromium-Pillared Clay as a Catalyst for Benzylic Oxidation and Oxidative Deprotection of Benzyl Ethers and Benzylamines: a Simple and Convenient Procedure,” The Journal of Organic Chemistry, Vol. 57, No. 22, 1992, pp. 5841-5844. doi:10.1021/jo00048a013
[10] J. Muzart and A. N’Ait Ajjou, “Chromium-Promoted Benzylic Oxidations by tert-Butyl Hydroperoxide: A New Catalyst and a Comparison of the Different Procedures,” Synthetic Communications, Vol. 23, No. 15, 1993, pp. 2113-2118. doi:10.1080/00397919308018604
[11] S. Boitsov, A. Riahi and J. Muzart, “Chromium(VI) Oxide-Catalysed Oxidations by tert-Butyl Hydroperoxide Using Benzotrifluoride as Solvent,” Comptes Rendus de l’Académie des Sciences-Series IIC-Chemistry, Vol. 3, No. 9, 2000, pp. 747-750. doi:10.1016/S1387-1609(00)01156-7
[12] J. Muzart, “Practical ChromiumVI Oxide-Catalyzed Benzylic Oxidations Using 70% tert-Butyl Hydroperoxide,” Tetrahedron Letters, Vol. 28, No. 19, 1987, pp. 2131- 2132. doi:10.1016/S0040-4039(00)96061-1
[13] Z. Lounis, A. Riahi, F. Djafri and J. Muzart, “Chromium-Exchanged Zeolite (CrE-ZSM-5) as Catalyst for Alcohol Oxidation and Benzylic Oxidation with t-BuOOH,” Applied Catalysis A: General, Vol. 309, No. 2, 2006, pp. 270-272. doi:10.1016/j.apcata.2006.05.015
[14] M. Selvaraj and C. S. Ha, “Highly Selective Synthesis of Enones from Benzylic Compounds over CrSBA-15,” Catalysis Today, Vol. 175, No. 1, 2011, pp. 546-551. doi:10.1016/j.cattod.2011.04.011
[15] M. Selvaraj, D. W. Park, S. Kawi and I. Kim, “Selective Synthesis of Benzophenone over Two-Dimentional Mesostructured CrSBA-15,” Applied Catalysis A: General, Vol. 415-416, 2012, pp. 17-21. doi:10.1016/j.apcata.2011.11.031
[16] A. J. Catino, J. M. Nichols, H. Choi, S. Gottipamula and M. P. Doyle, “Benzylic Oxidation Catalyzed by Dirhodium(II,III) Caprolactamate,” Organic Letters, Vol. 7, No. 23, 2005, pp. 5167-5170. doi:10.1021/ol0520020
[17] S.-I. Murahashi, N. Komiya, Y. Oda, T. Kuwabara and T. Naota, “Ruthenium-Catalyzed Oxidation of Alkanes with tert-Butyl Hydroperoxide and Peracetic Acid,” The Journal of Organic Chemistry, Vol. 65, No. 26, 2000, pp. 9186-9193. doi:10.1021/jo001348f
[18] Y. Bonvin, et al., “Bismuth-Catalyzed Benzylic Oxidations with tert-Butyl Hydroperoxide,” Organic Letters, Vol. 7, No. 21, 2005, pp. 4549-4552. doi:10.1021/ol051765k
[19] M. Nakanishi and C. Bolm, “Iron-Catalyzed Benzylic Oxidation with Aqueous tert-Butyl Hydroperoxide,” Advanced Synthesis & Catalysis, Vol. 349, No. 6, 2007, pp. 861-864. doi:10.1002/adsc.200600553
[20] A. Dhakshinamoorthy, M. Alvaro and H. Garcia, “Metal Organic Frameworks as Efficient Heterogeneous Catalysts for the Oxidation of Benzylic Compounds with t-Butylhydroperoxide,” Journal of Catalysis, Vol. 267, No. 1, 2009, pp. 1-4. doi:10.1016/j.jcat.2009.08.001
[21] H. Li, Z. Li and Z. Shi, “Gold-Catalyzed Benzylic Oxidation to Carbonyl Compounds,” Tetrahedron, Vol. 65, No. 9, 2009, pp. 1856-1858. doi:10.1016/j.tet.2008.12.055
[22] A. S. Burange, S. R. Kale and R. V. Jayaram, “Oxidation of Alkyl Aromatics to Ketones by tert-Butyl Hydroperoxide on Manganese Dioxide Catalyst,” Tetrahedron Letters, Vol. 53, No. 24, 2012, pp. 2989-2992. doi:10.1016/j.tetlet.2012.03.091
[23] M. Rogovin and R. Neumann, “Silicate Xerogels Containing Cobalt as Heterogeneous Catalysts for the Side-Chain Oxidation of Alkyl Aromatic Compounds with tert-Butyl Hydroperoxide,” Journal of Molecular Catalysis A: Chemical, Vol. 138, No. 2-3, 1999, pp. 315-318. doi:10.1016/S1381-1169(98)00207-6
[24] M. Jurado-Gonzalez, A. C. Sullivan and J. R. H. Wilson, “Allylic and Benzylic Oxidation Using Cobalt(II) Alkyl Phosphonate Modified Silica,” Tetrahedron Letters, Vol. 44, No. 22, 2003, pp. 4283-4286. doi:10.1016/S0040-4039(03)00833-5
[25] C. Wang, Y. Zhang, B. Yuan and J. Zhao, “Synthesis, Single Crystal Structures and Efficient Catalysis for Tetralin Oxidation of Two Novel Complexes of Cu(II) with 2-Aminomethyl Pyridine,” Journal of Molecular Catalysis A: Chemical, Vol. 333, No. 1-2, 2010, pp. 173-179. doi:10.1016/j.molcata.2010.10.014
[26] S. J. Singh and R. V. Jayaram, “Oxidation of Alkylaromatics to Benzylic Ketones Using TBHP as an Oxidant over LaMO3 (M = Cr, Co, Fe, Mn, Ni) Perovskites,” Catalysis Communications, Vol. 10, No. 15, 2009, pp. 2004-2007. doi:10.1016/j.catcom.2009.07.018
[27] M. Ghiaci, F. Molaie, M. E. Sedaghat and N. Dorostkar, “Metalloporphyrin Covalently Bound to Silica. Preparation, Characterization and Catalytic Activity in Oxidation of Ethyl Benzene,” Catalysis Communications, Vol. 11, No. 8, 2010, pp. 694-699. doi:10.1016/j.catcom.2010.01.023
[28] G. Rothenberg, L. Feldberg, H. Wiener and Y. Sasson, “Copper-Catalyzed Homolytic and Heterolytic Benzylic and Allylic Oxidation Using tert-Butyl Hydroperoxide,” Journal of the Chemical Society, Perkin Transactions, Vol. 2, No. 11, 1998, pp. 2429-2434.
[29] T. Punniyamurthy and L. Rout, “Recent Advances in Copper-Catalyzed Oxidation of Organic Compounds,” Coordination Chemistry Reviews, Vol. 252, No. 1-2, 2008, pp. 134-154. doi:10.1016/j.ccr.2007.04.003
[30] B. Cornils, “Industrial Aqueous Biphasic Catalysis: Status and Directions,” Organic Process Research & Development, Vol. 2, No. 2, 1998, 121-127. doi:10.1021/op970057e
[31] B. Cornils and W. A. Herrmann, “Applied Homogeneous Catalysis with Organometallic Compounds,” 2nd Edition, Wiley-VCH, Weinheim, 2002.
[32] F. Joó and á. Kathó, “Recent Developments in Aqueous Organometallic Chemistry and Catalysis,” Journal of Molecular Catalysis A: Chemical, Vol. 116, No. 1-2, 1997, pp. 3-26. doi:10.1016/S1381-1169(96)00075-1
[33] A. Nait Ajjou and H. Alper, “A New, Efficient, and in Some Cases Highly Regioselective Water-Soluble Polymer Rhodium Catalyst for Olefin Hydroformylation,” Journal of the American Chemical Society, Vol. 120, No. 7, 1998, 1466-1468. doi:10.1021/ja973048u
[34] M. C. K.-B. Djoman and A. Nait Ajjou, “The Hydration of Nitriles Catalyzed by Water-Soluble Rhodium Complexes,” Tetrahedron Letters, Vol. 41, No. 25, 2000, pp. 4845-4849. doi:10.1016/S0040-4039(00)00743-7
[35] A. Nait Ajjou and J.-L. Pinet, “The Biphasic Transfer Hydrogenation of Aldehydes and Ketones with Isopropanol Catalyzed by Water-Soluble Rhodium Complexes,” Journal of Molecular Catalysis A: Chemical, Vol. 214, No. 2, 2004, pp. 203-206. doi:10.1016/j.molcata.2004.01.004
[36] A. Nait Ajjou, “First Example of Water-Soluble Transition-Metal Catalysts for Oppenauer-Type Oxidation of Secondary Alcohols,” Tetrahedron Letters, Vol. 42, No. 1, 2001, pp. 13-15. doi:10.1016/S0040-4039(00)01882-7
[37] A. Nait Ajjou and J.-L. Pinet, “Oppenauer-Type Oxidation of Secondary Alcohols Catalyzed by Homogeneous Water-Soluble Complexes,” Canadian Journal of Chemistry, Vol. 83, No. 6-7, 2005, pp. 702-710. doi:10.1139/v05-037
[38] A. Robichaud and A. Nait Ajjou, “First Example of Direct Reductive Amination of Aldehydes with Primary and Secondary Amines Catalyzed by Water-Soluble Transition Metal Catalysts,” Tetrahedron Letters, Vol. 47, No. 22, 2006, pp. 3633-3636. doi:10.1016/j.tetlet.2006.03.153
[39] G. Ferguson and A. Nait Ajjou, “Solvent-Free Oxidation of Alcohols by t-Butyl Hydroperoxide Catalyzed by Water-Soluble Copper Complex,” Tetrahedron Letters, Vol. 44, No. 51, 2003, pp. 9139-9142. doi:10.1016/j.tetlet.2003.10.052
[40] J. Boudreau, M. Doucette and A. Nait Ajjou, “A New and Highly Efficient Water-Soluble Copper Complex for the Oxidation of Secondary 1-Heteroaryl Alcohols by tert-Butyl Hydroperoxide,” Tetrahedron Letters, Vol. 47, No. 11, 2006, pp. 1695-1698. doi:10.1016/j.tetlet.2006.01.061
[41] A. Nait Ajjou and G. Ferguson, “An Unprecedented Highly Efficient Solvent-Free Oxidation of Alkynes to α,β-Acetylenic Ketones with tert-Butyl Hydroperoxide Catalyzed by Water-Soluble Copper Complex,” Tetrahedron Letters, Vol. 47, No. 22, 2006, pp. 3719-3722. doi:10.1016/j.tetlet.2006.03.140
[42] J. Muzart and A. N’Ait Ajjou, “Chromium-Catalyzed Homolytic Scission of Organic Peroxides with t-Butyl Hydroperoxide and its Relation to Benzylic Oxidation,” Journal of Molecular Catalysis, Vol. 92, No. 2, 1994, pp. 141-147. doi:10.1016/0304-5102(94)00068-9
[43] J. Muzart and A. N’Ait Ajjou, “Highly Efficient Oxygen Transfer from tert-Butyl Hydroperoxide to Benzylic Carbons Catalyzed by Chromium(VI) Oxide under High Substrate/ Hydroperoxide Ratios,” Journal of Molecular Catalysis, Vol. 92, No. 3, 1994, pp. 277-283. doi:10.1016/0304-5102(94)00082-4

  
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