Recent Advance in Green Catalytic Oxidation of Alcohols to Aldehydes and Ketones with Hydrogen Peroxide as Oxidant

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Abstract:

. New developments in green catalytic oxidations of alcohols with H2O2 as oxidant in last decade are reviewed. Emphasis is placed on introducing the heterogeneous catalysts supported on different material in various of reactions, mechanism features are discussed as well.

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Periodical:

Advanced Materials Research (Volumes 1049-1050)

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158-166

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Online since:

October 2014

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[1] Fey T, Fischer H, Albert K, et al. Silica-supported TEMPO catalysts: Synthesis and application in the Anelli oxidation of alcohols. [J]. The Journal of organic chemistry, 2001 66 (24) 8154-8159.

DOI: 10.1021/jo010535q

Google Scholar

[2] Sato K, Aoki M, Takagi J. Organic solvent-and halide-free oxidation of alcohols with aqueous hydrogen peroxide[J]. Journal of the American Chemical Society, 1997 119(50) 12386-12387.

DOI: 10.1021/ja973412p

Google Scholar

[3] Islam S M, Roy A S, Mondal P, Salam N. Synthesis, catalytic oxidation and oxidative bromination reaction of a reusable polymer anchored oxovanadium (IV) complex. [J]. Journal of Molecular Catalysis A: Chemical, 2012 (358) 38-48.

DOI: 10.1016/j.molcata.2012.02.009

Google Scholar

[4] Herbert M, Montilla F, Galindo A. Synthesis and theoretical analysis of palladium complexes of polydimethylsiloxane functionalised pyridine and their catalytic activity in alcohol oxidations under low polar conditions. [J]. Polyhedron, 2010 29(18) 3287-3293.

DOI: 10.1016/j.poly.2010.09.004

Google Scholar

[5] Gligorich K M, Sigman M S. Recent advancements and challenges of palladium II-catalyzed oxidation reactions with molecular oxygen as the sole oxidant. [J]. Chemical Communications, 2009 (26) 3854-3867.

DOI: 10.1039/b902868d

Google Scholar

[6] Xiaoli Wang, Gongde Wu, Junping Li, Ning Zhao, Wei Wei, Yuhan Sun. Surface-modified improvement in catalytic performance of Cr (salen) complexes immobilized on MCM-41 in solvent-free selective oxidation of benzyl alcohol. [J]. Catalysis Letters, 2007 119 (1-2) 87-94.

DOI: 10.1007/s10562-007-9197-3

Google Scholar

[7] Mingxia Zhu, Bodong Li, Youzhu Yuan. Oxidant-dependent selective oxidation of alcohols utilizing multinuclear copper-triethanolamine complexes. [J]. Tetrahedron, 2008 64 (39) 9239-9243.

DOI: 10.1016/j.tet.2008.07.038

Google Scholar

[8] Sanderson W R. Cleaner industrial processes using hydrogen peroxide. [J]. Pure and applied chemistry, 2000 72 (7) 1289-1304.

DOI: 10.1351/pac200072071289

Google Scholar

[9] Bilis G, Christoforidis K C, Louloudia M. Hydrocarbon oxidation by homogeneous and heterogeneous non-heme iron (III) catalysts with H2O2. [J]. Catalysis Today, 2010 157 (1) 101-106.

DOI: 10.1016/j.cattod.2010.03.063

Google Scholar

[10] Noshiranzadeh N, Bikas R, Ślepokura K, Mayeli M, Tadeusz L. Synthesis, characterization and catalytic activity of new Cr (III) complex in oxidation of primary alcohols to aldehydes. [J]. Inorganica Chimica Acta, 2014 421 176-182.

DOI: 10.1016/j.ica.2014.05.026

Google Scholar

[11] Bahramian B, Mirkhani V, Amin A H. Water-soluble manganese (III) salen complex as a mild and selective catalyst for oxidation of alcohols. [J]. Applied Catalysis A: General, 2006 315 52-57.

DOI: 10.1016/j.apcata.2006.08.037

Google Scholar

[12] Sato K, Aoki M, Noyori R. Hydrogen peroxide oxidation of benzylic alcohols to benzaldehy- des and benzoic acids under halide-free conditions. [J]. Tetrahedron letters, 1998 39 (41) 7549-7552.

DOI: 10.1016/s0040-4039(98)01642-6

Google Scholar

[13] Jacobson S E, Muccigrosso D A, Mares F. Oxidation of alcohols by molybdenum and tungsten peroxo complexes. [J]. The Journal of Organic Chemistry, 1979 44(6) 921-924.

DOI: 10.1021/jo01320a006

Google Scholar

[14] Sheldon R A, Arends I, Dijksman A. New developments in catalytic alcohol oxidations for fine chemicals synthesis. [J]. Catalysis Today, 2000 57 (1) 157-166.

DOI: 10.1016/s0920-5861(99)00317-x

Google Scholar

[15] Alexander M. Kirillov , Georgiy B. Shul'pinb. Pyrazinecarboxylic acid and analogs: Highly efficient co-catalysts in the metal-complex-catalyzed oxidation of organic compounds Coordination Chemistry Reviews 2013 (257) 732-754.

DOI: 10.1016/j.ccr.2012.09.012

Google Scholar

[16] Kon Y, Usui Y, Sato K. Oxidation of allylic alcohols to α, β-unsaturated carbonyl compounds with aqueous hydrogen peroxide under organic solvent-free conditions[J]. Chemical Communications, 2007 (42) 4399-4400.

DOI: 10.1039/b708612a

Google Scholar

[17] Stolle A, Ondruschka B, Morgenthal I, Andersen, O. Metallic short fibers for liquid-phase oxidation reactions[J]. Journal of Molecular Catalysis A: Chemical, 2011 335(1) 228-235.

DOI: 10.1016/j.molcata.2010.11.038

Google Scholar

[18] Noshiranzadeh N, Mayeli M, Bikas R. Selective catalytic oxidation of benzyl alcohol to benzaldehyde by a mononuclear oxovanadium (V) complex of a bis (phenolate) ligand containing bulky tert-butyl substituents[J]. Transition Metal Chemistry, 2014 39(1) 33-39.

DOI: 10.1007/s11243-013-9769-6

Google Scholar

[19] Noshiranzadeh N, Emami M, Ślepokura K, Lis T. Synthesis, characterization and catalytic reactivity of Mn (III) complexes with a scorpion-like bis (phenolate) ligand: Selective oxidation of primary alcohols to aldehydes[J]. Polyhedron, 2014 72 56-65.

DOI: 10.1016/j.poly.2014.01.020

Google Scholar

[20] Yan Leng, Pingping Zhao, Mingjue Zhang, Jun Wang. Mino functionalized bipyridine-hetero- polyacid ionic hybrid: A recyclable catalyst for solvent-free oxidation of benzyl alcohol with H2O2. [J]. Journal of Molecular Catalysis A: Chemical, 2012 358 67-72.

DOI: 10.1016/j.molcata.2012.02.012

Google Scholar

[21] Han H, Zhang S, Hou H. Fe (Cu)‐Containing Coordination Polymers: Syntheses, Crystal Structures, and Applications as Benzyl Alcohol Oxidation Catalysts[J]. European journal of inorganic chemistry, 2006(8): 1594-1600.

DOI: 10.1002/ejic.200500808

Google Scholar

[22] Kato C N, Hasegawa M, Sato T, Yoshizawa A. Microporous dinuclear copper (II) trans-1, 4-cyclohexanedicarboxylate: heterogeneous oxidation catalysis with hydrogen peroxide and X-ray powder structure of peroxo copper (II) intermediate. [J]. Journal of Catalysis, 2005 230 (1) 226-236.

DOI: 10.1016/j.jcat.2004.11.032

Google Scholar

[23] Polshettiwar V, Len C, Fihri A. Silica-supported palladium: Sustainable catalysts for cross-coupling reactions[J]. Coordination Chemistry Reviews, 2009, 253(21): 2599-2626.

DOI: 10.1016/j.ccr.2009.06.001

Google Scholar

[24] Sahu D, Sarmah C, Das P. A highly efficient and recyclable silica-supported palladium catalyst for alcohol oxidation reaction. [J]. Tetrahedron Letters, 2014 55(23) 3422-3425.

DOI: 10.1016/j.tetlet.2014.04.071

Google Scholar

[25] Rahman A, Pullabhotla V S R, Jonnalagadda S B. Selective oxidation of p-nitrobenzyl alcohol to p-nitrobenzaldehyde with 10% Ni silica with 30% H2O2 in acetonitrile solvent. [J]. Catalysis Communications, 2008 9(14) 2417-2421.

DOI: 10.1016/j.catcom.2008.06.004

Google Scholar

[26] Sousa J L C, Santos I C M S, Simões M M Q, Iron (III)-substituted polyoxotungstates immobilized on silica nanoparticles: Novel oxidative heterogeneous catalysts[J]. Catalysis Communications, 2011 12(6) 459-463.

DOI: 10.1016/j.catcom.2010.11.005

Google Scholar

[27] Estrada A C, Simões M M Q, Santos I C M S, et al. Iron-substituted polyoxotungstates as catalysts in the oxidation of indane and tetralin with hydrogen peroxide[J]. Applied Catalysis A: General, 2009 366(2) 275-281.

DOI: 10.1016/j.apcata.2009.07.022

Google Scholar

[28] Farsani M R, Yadollahi B. Synthesis, characterization and catalytic performance of a Fe polyoxometalate/silica composite in the oxidation of alcohols with hydrogen peroxide. [J]. Journal of Molecular Catalysis A: Chemical, 2014 392 8-15.

DOI: 10.1016/j.molcata.2014.05.001

Google Scholar

[29] Mahdavi V, Mardani M, Malekhosseini M. Oxidation of alcohols with tert-butylhydroperoxide catalyzed by Mn (II) complexes immobilized in the pore channels of mesoporous hexagonal molecular sieves. [J]. Catalysis Communications, 2008 9(13) 2201-2204.

DOI: 10.1016/j.catcom.2008.05.008

Google Scholar

[30] Karthikeyan G, Pandurangan A. Heteropolyacid (H3PW12O40) supported MCM-41: An efficient solid acid catalyst for the green synthesis of xanthenedione derivatives[J]. Journal of Molecular Catalysis A: Chemical, 2009 311(1) 36-45.

DOI: 10.1016/j.molcata.2009.06.020

Google Scholar

[31] Rong Tan , Cheng Liu , Ningdong Feng , Weiguo Zheng. Phosphotungstic acid loaded on hydrophilic ionic liquid modified SBA-15 for selective oxidation of alcohols with aqueous H2O2. [J]. Microporous and Mesoporous Materials, 2012 158 77-87.

DOI: 10.1016/j.micromeso.2012.03.023

Google Scholar

[32] Xinbo Dong , Danjun Wang, Kebin Li, Yanzhong Zhen, Ganglin Xue. Vanadium-substituted heteropolyacids immobilized on amine-functionalized mesoporous MCM-41: A recyclable catalyst for selective oxidation of alcohols with H2O2. [J]. Materials Research Bulletin, 2014 57 210-220.

DOI: 10.1016/j.materresbull.2014.05.041

Google Scholar

[33] Karimi B, Rostami F B, Khorasani M. Selective oxidation of alcohols with hydrogen peroxide catalyzed by tungstate ions (WO4=) supported on periodic mesoporous organosilica with imidazolium frameworks (PMO-IL). [J]. Tetrahedron, 2014 1-6.

DOI: 10.1016/j.tet.2014.04.030

Google Scholar

[34] Lin Qi, Jing Wang, Liwei Zheng. A synergistic effect in the combination of H2O2, FeAPO-5 and NaBr for selective oxidation of benzyl alcohols[J]. Catalysis Communications, 2011 16 (1) 225-228.

DOI: 10.1016/j.catcom.2011.09.035

Google Scholar

[35] Aizhong Jia, Lan-Lan Lou, Cui Zhang, Shuangxi Liu. Selective oxidation of benzyl alcohol to benzaldehyde with hydrogen peroxide over alkali-treated ZSM-5 zeolite catalysts. [J] Journal of Molecular Catalysis A: Chemical, 2009 (306) 123-129.

DOI: 10.1016/j.molcata.2009.02.035

Google Scholar

[36] Bansal, V. K., Thankachan, P. P., Prasad, R. Oxidation of benzyl alcohol and styrene using H2O2 catalyzed by tetraazamacrocycle complexes of Cu(II) and Ni(II) encapsulated in zeolite-Y. Applied Catalysis A: General, 2010 (381) 8-17.

DOI: 10.1016/j.apcata.2010.03.027

Google Scholar

[37] Ezabadi A, Najafi G R, Hashemi M M. A green and efficient oxidation of benzylic alcohols using H2O2 catalyzed by montmorillonite K-10 supported CoCl2. [J]. Chinese Chemical Letters, 2008 19 (11) 1277-1280.

DOI: 10.1016/j.cclet.2008.09.010

Google Scholar

[38] Najafi G R. A green and efficient oxidation of benzylic alcohols using H2O2 catalyzed by Montmorillonite-K10 supported MnCl2. [J]. Chinese Chemical Letters, 2010 21(10) 1162-1164.

DOI: 10.1016/j.cclet.2010.05.031

Google Scholar

[39] Peyrovi M H, Mahdavi V, Salehi M A, Mahmoodian R. Oxidation of alcohols with tert-butylhydroperoxide catalyzed by Co (II) complexes immobilized between silicate layers of bentonite[J]. Catalysis Communications 2005 6(7) 476-479.

DOI: 10.1016/j.catcom.2005.04.010

Google Scholar

[40] Gongde Wu , Xiaoli Wang, Junping Li, Ning Zhao, Wei Wei, Yuhan Sun. A new route to synthesis of sulphonato-salen-chromium(III) hydrotalcites: Highly selective catalysts for oxidationof benzyl alcohol to benzaldehyde [J]Catalysis Today 2008 (131) 402-407.

DOI: 10.1016/j.cattod.2007.10.085

Google Scholar

[41] Nunes C A, Guerreiro M C. Chemometric approaches on glycerol oxidation with H2 O2 over supported gold nanoparticles. [J]. Journal of Molecular Catalysis A: Chemical, 2013 370 145-151.

DOI: 10.1016/j.molcata.2013.01.006

Google Scholar

[42] M. Sankar, N. Dimitratos, D.W. Knight, A.F. Carley, R. Tiruvalam, C.J. Kiely, D. Thomas, G.J. Hutchings, Oxidation of Glycerol to Glycolate by using Supported Gold and Palladium NanoparticlesChemSusChem, 2009 (2) 1145-1151.

DOI: 10.1002/cssc.200900133

Google Scholar

[43] Shokrolahi A, Zali A, Keshavarz M H. Oxidation of organic compounds by sulfonated porous carbon and hydrogen peroxide. [J]. Chinese Journal of Catalysis, 2010 31(11) 1427-1432.

DOI: 10.1016/s1872-2067(10)60127-1

Google Scholar

[44] Manyar H G, Kumar A. Supported polyperoxometallates: Highly selective catalyst for oxidation of alcohols to aldehydes[J]. Journal of Molecular Catalysis A: Chemical, 2006 243(2) 244-252.

DOI: 10.1016/j.molcata.2005.09.036

Google Scholar

[45] Mahdavi V, Soleimani S. Novel synthesis of manganese and vanadium mixed oxide (V2O5/OMS-2) as an efficient and selective catalyst for the oxidation of alcohols in liquid phase. [J]. Materials Research Bulletin, 2014 51 153-160.

DOI: 10.1016/j.materresbull.2013.11.042

Google Scholar

[46] Hamamoto H, Suzuki Y, Yamada Y, et al. A Recyclable Catalytic System Based on a Temperature‐Responsive Catalyst[J]. Angewandte Chemie, 2005 117(29) 4612-4614.

DOI: 10.1002/ange.200500574

Google Scholar

[47] Bianchini G, Crucianelli M, Angelis F D. Highly efficient C–H insertion reactions of hydrogen peroxide catalyzed by homogeneous and heterogeneous methyltrioxorhenium systems in ionic liquids[J]. Tetrahedron letters, 2005 46(14) 2427-2432.

DOI: 10.1016/j.tetlet.2005.02.056

Google Scholar