Catalytic Oxidation of Alcohols: Recent Advances

Advances in Organometallic Chemistry

Volumn 63, Issue , 2015, Pages 91-174

  Kopylovich, Maximilian N ^a   Ribeiro, Ana P C ^a   Alegria, Elisabete C B A ^a,b   Martins, Nuno M R ^a   Martins, Luísa M D R S ^a,b   Pombeiro, Armando J L ^a  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^b INSTITUTO SUPERIOR DE ENGENHARIA DE LISBOA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84943147106     PISSN: 00653055     EISSN: None     Source Type: Book Series    
DOI: 10.1016/bs.adomc.2015.02.004     Document Type: Chapter

References (330)

1. Tojo G, Fernandez M. Oxidation of Alcohols to Aldehydes and Ketones. New York, USA: Springer; 2006.
2. Mallat T, Baiker A. Oxidation of alcohols with molecular oxygen on solid catalysts. Chem Rev. 2004;104:3037-3058.
3. Sarathy SM, Oßwald P, Hansen N, Kohse-Höinghaus K. Alcohol combustion chemistry, progress in energy and combustion. Science. 2014;44:40-102.
4. Bianchini C, Shen PK. Palladium-based electrocatalysts for alcohol oxidation in half cells and in direct alcohol fuel cells. Chem Rev. 2009;109:4183-4206.
5. Sheldon RA, Arends IWCE, Dijksman A. New developments in catalytic alcohol oxidations for fine chemicals synthesis. Catal Today. 2000;57:157-166.
6. Allen SE, Walvoord RR, Padilla-Salinas R, Kozlowski MC. Aerobic copper-catalyzed organic reactions. Chem Rev. 2013;113:6234-6645.
7. Sheldon RA, Arends IWCE, Ten Brink G-J, Dijksman A. Green catalytic oxidations of alcohols. Acc Chem Res. 2002;35:774-781.
8. Dobereiner GE, Crabtree RH. Dehydrogenation as a substrate-activating strategy in homogeneous transition-metal catalysis. Chem Rev. 2010;110:681-703.
9. Sigman MS, Jensen DR. Ligand-modulated palladium-catalyzed aerobic alcohol oxidations. Acc Chem Res. 2006;39:221-229.
10. Ryland BL, Stahl SS. Practical aerobic oxidations of alcohols and amines with homogeneous copper/TEMPO and related catalyst systems. Angew Chem Int Ed Engl. 2014;53:8824-8838.
11. Liang Z-X, Zhao TS. Catalysts for Alcohol-Fuelled Direct Oxidation Fuel Cells. Cambridge: RSC; 2012.
12. Trincado M, Banerjee D, Grutzmacher H. Molecular catalysts for hydrogen production from alcohols. Energy Environ Sci. 2014;7:2464-2503.
13. Backvall J-E, ed. Modern Oxidation Methods. Weinheim: Wiley; 2010.
14. Arends IWCE, Sheldon RA. Modern oxidation of alcohols using environmentally benign oxidants. In: Backvall J-E, ed. Modern Oxidation Methods. Weinheim: Wiley; 2010.
15. Ishii Y, Sakaguchi S, Obora Y. Aerobic oxidations and related reactions catalyzed by n-hydroxyphthalimide. In: Backvall J-E, ed. Modern Oxidation Methods. Weinheim: Wiley; 2010
16. Browne WR, de Boer JW, Pijper D, Brinksma J, Hage R, Feringa BL. Manganese-catalyzed oxidation with hydrogen peroxide. In: Backvall J-E, ed. Modern Oxidation Methods. Weinheim: Wiley; 2010
17. Murahashi S-I, Komiya N. Ruthenium-catalyzed oxidation for organic synthesis. In: Backvall J-E, ed. Modern Oxidation Methods. Weinheim: Wiley; 2010.
18. Mizuno N. Modern Heterogeneous Oxidation Catalysis. Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA; 2009.
19. Sheldon RA, Arends IWCE. Organocatalytic oxidations mediated by nitroxyl radicals. Adv Synth Catal. 2004;346:1051-1071.
20. Silva JAL, Silva JJRF, Pombeiro AJL. Oxovanadium complexes in catalytic oxidations. Coord Chem Rev. 2011;255:2232-2248.
21. Kumpulainen ETT, Koskinen AMP. Catalytic activity dependency on catalyst components in aerobic copper-TEMPO oxidation. Chem Eur J. 2009;15:10901-10911.
22. Hoover JM, Ryland BL, Stahl SS. Copper/TEMPO-catalyzed aerobic alcohol oxidation: mechanistic assessment of different catalyst systems. ACS Catal. 2013;3:2599-2605.
23. Parmeggiani C, Cardona F. Transition metal based catalysts in the aerobic oxidation of alcohols. Green Chem. 2012;14:547-564.
24. Wigington BN, Drummond ML, Cundari TR, Thorn DL, Hanson SK, Scott SL. A biomimetic pathway for vanadium-catalyzed aerobic oxidation of alcohols: evidence for a base-assisted dehydrogenation mechanism. Chem Eur J. 2012;18: 14981-14988.
25. Zakzeski J, Bruijnincx PCA, Jongerius AL, Weckhuysen BM. The catalytic valorization of lignin for the production of renewable chemicals. Chem Rev. 2010;10:3552-3599.
26. Roberts SM, Whittall J. Regio- and Stereo-Controlled Oxidations and Reductions. Weinheim: Wiley-VCH; 2007.
27. Griffith WP. Ruthenium Oxidation Complexes. Dordrecht: Springer; 2011.
28. Schultz MJ, Sigman MS. Recent advances in homogeneous transition metalcatalyzed aerobic alcohol oxidations. Tetrahedron. 2006;62:8227-8241
29. Zhan B-Z, Thompson A. Recent developments in the aerobic oxidation of alcohols. Tetrahedron. 2004;60:2917-2935.
30. Besson M, Gallezot P. Selective oxidation of alcohols and aldehydes on metal catalysts. Catal Today. 2000;57:127-141.
31. Figiel PJ, Kirillov AM, Guedes da Silva MFC, Lasri J, Pombeiro AJL. Self-assembled dicopper(II) diethanolaminate cores for mild aerobic and peroxidative oxidation of alcohols. Dalton Trans. 2010;39:9879-9888.
32. Figiel PJ, Kirillov AM, Karabach YY, Kopylovich MN, Pombeiro AJL. Mild aerobic oxidation of benzyl alcohols to benzaldehydes in water catalyzed by aqua-soluble multicopper(II) triethanolaminate compounds. J Mol Catal A Chem. 2009;305:178-182.
33. Zhang G, Proni G, Zhao S, et al. Chiral tetranuclear and dinuclear copper(II) complexes for TEMPO-mediated aerobic oxidation of alcohols: are four metal centres better than two? Dalton Trans. 2014;43:12313-12320.
34. Raisanen MT, Al-Hunaiti A, Atosuo E, Kemell M, Leskela M, Repo T. Mn(II) acetate: an efficient and versatile oxidation catalyst for alcohols. Catal Sci Technol. 2014;4:2564-2573.
35. John LC, Gunay A, Wood AJ, Emmert MH. Catalysts for convenient aerobic alcohol oxidations in air: systematic ligand studies in Pd/pyridine systems. Tetrahedron. 2013;69:5758-5764.
36. Bailie DS, Clendenning GMA, McNamee L, Muldoon MJ. Anionic N,O-ligated Pd(II) complexes: highly active catalysts for alcohol oxidation. Chem Commun. 2010;46:7238-7240.
37. Gowrisankar S, Neumann H, Gördes D, Thurow K, Jiao H, Beller M. A convenient and selective palladium-catalyzed aerobic oxidation of alcohols. Chem Eur J. 2013;19:15979-15984.
38. 2 intermediate in aerobic oxidation catalysis. Angew Chem Int Ed Engl. 2014;53:5648-5652.
39. Giachi G, Frediani M, Oberhauser W, Passaglia E. Aerobic alcohol oxidation catalyzed by polyester-based Pd(II) macrocomplexes. J Polym Sci A Polym Chem. 2012;50:2725-2731.
40. Mugemana C, Chen B-T, Bukhryakov KV, Rodionov V. Star block-copolymers: enzyme-inspired catalysts for oxidation of alcohols in water. Chem Commun. 2014;50:7862-7865.
41. 2 with TEMPO and a tetradentate polymer based pyridyl-imine ligand. Appl Catal A Gen. 2012;413-414:332-339.
42. Zhang G, Han X, Luan Y, Wang Y, Wen X, Ding C. l-Proline: an efficient N, O-bidentate ligand for copper-catalyzed aerobic oxidation of primary and secondary benzylic alcohols at room temperature. Chem Commun. 2013;49:7908-7910.
43. Kirillov AM, Kirillova MV, Shul'pina LS, et al. Mild oxidative functionalization of alkanes and alcohols catalyzed by new mono- and dicopper(II) aminopolyalcoholates. J Mol Catal A Chem. 2011;350:26-34.
44. Mahmudov KT, Kopylovich MN, Silva MFCG, Figiel PJ, Karabach YY, Pombeiro AJL. New copper(II) dimer with 3-(2-hydroxy-4-nitrophenylhydrazo)- pentane-2,4-dione and its catalytic activity in cyclohexane and benzyl alcohol oxidations. J Mol Catal A Chem. 2010;318:44-50.
45. Kopylovich MN, Mahmudov KT, Silva MFCG, et al. Ortho-hydroxyphenylhydrazo-ß-diketones: tautomery, coordination ability, and catalytic activity of their copper(II) complexes toward oxidation of cyclohexane and benzylic alcohols. Inorg Chem. 2011;50:918-931.
46. Kopylovich MN, Karabach YY, Mahmudov KT, et al. Heterometallic copper(II)-potassium 3D coordination polymers driven by multifunctionalized azo derivatives of ß-diketones. Cryst Growth Des. 2011;11:4247-4252.
47. Kopylovich MN, Gajewska MJ, Mahmudov KT, et al. Copper(II) complexes with a new carboxylic-functionalized arylhydrazone of ß-diketone as effective catalysts for acid-free oxidations. New J Chem. 2012;36:1646-1654.
48. Kopylovich MN, Mizar A, Silva MFCG, MacLeod TCO, Mahmudov KT, Pombeiro AJL. Template syntheses of copper(II) complexes from arylhydrazones of malononitrile and their catalytic activity towards alcohol oxidations and the nitroaldol reaction: hydrogen bondassisted ligand liberation and E/Z isomerisation. Chem Eur J. 2013;19:588-600
49. Mahmudov KT, Kopylovich MN, Sabbatini A, et al. Cooperative metal-ligand assisted E/Z isomerization and cyano activation at Cu(II) and Co(II) complexes of arylhydrazones of active methylene nitriles. Inorg Chem. 2014;53:9946-9958.
50. Borthakur R, Asthana M, Saha M, Kumar A, Pal AK. An efficient oxidation of alcohols using a new trinuclear copper complex as a reusable catalyst under solvent free conditions. RSC Adv. 2014;4:21638-21643.
51. Nasani R, Saha M, Mobin SM, et al. Copper-organic frameworks assembled from in situ generated 5-(4-pyridyl)tetrazole building blocks: synthesis, structural features, topological analysis and catalytic oxidation of alcohols. Dalton Trans. 2014;43: 9944-9954.
52. Fei H, Shin J, Meng YS, et al. Reusable oxidation catalysis using metalmonocatecholato species in a robust metal-organic framework. J Am Chem Soc. 2014;136:4965-4973.
53. Fernandes RR, Lasri J, da Silva MFCG, da Silva JAL, da Silva JJR F, Pombeiro AJL. Bis- and tris-pyridyl amino and imino thioether Cu and Fe complexes. Thermal and microwave-assisted peroxidative oxidations of 1-phenylethanol and cyclohexane in the presence of various N-based additives. J Mol Catal A Chem. 2011;351: 100-111.
54. Fernandes RR, Lasri J, da Silva MFCG, da Silva JAL, Fraústo da Silva JJR, Pombeiro AJL. Mild alkane C-H and O-H oxidations catalysed by mixed-N, S copper, iron and vanadium systems. Appl Catal A Gen. 2011;402:110-120.
55. 2 as the oxidant. Chem Commun. 2013;49:5889-5891.
56. Al-Hunaiti A, Niemi T, Sibaouih A, Pihko P, Leskela M, Repo T. Solvent free oxidation of primary alcohols and diols using thymine iron(III) catalyst. Chem Commun. 2010;46:9250-9252.
57. Join B, Möller K, Ziebart C, et al. Selective ironcatalyzed oxidation of benzylic and allylic alcohols. Adv Synth Catal. 2011;353: 3023-3030.
58. Hanson SK, Wu R, Silks LAP. Mild and selective vanadium-catalyzed oxidation of benzylic, allylic, and propargylic alcohols using air. Org Lett. 2011;13:1908-1911.
59. 2-the cinnamic acid/ metavanadate system. Chem Eur J. 2010;16:6892-6899.
60. Sedai B, Díaz-Urrutia C, Baker RT,WuR, Silks LAP, Hanson SK. Comparison of copper and vanadium homogeneous catalysts for aerobic oxidation of lignin models. ACS Catal. 2011;1:794-804.
61. Son S, Toste FD. Non-oxidative vanadium-catalyzed C-O bond cleavage: application to degradation of lignin model compounds. Angew Chem Int Ed Engl. 2010;122:3879-3882.
62. Zhang G, Scott BL,WuR, Silks LAP, Hanson SK. Aerobic oxidation reactions catalyzed by vanadium complexes of bis(phenolate) ligands. Inorg Chem. 2012;51:7354-7361.
63. Dönges M, Amberg M, Stapf G, Kelm H, Bergsträßer U, Hartung J. cis-2,6- Bis-(methanolate)-piperidine oxovanadium(V) complexes as catalysts for oxidative alkenol cyclization by tert-butyl hydroperoxide. Inorg Chim Acta. 2014;420:120-134.
64. Han L, Xing P, Jiang B. Selective aerobic oxidation of alcohols to aldehydes, carboxylic acids, and imines catalyzed by a Ag-NHC complex. Org Lett. 2014;16:3428-3431.
65. Liu L, Yu M, Wayland BB, Fu X. Aerobic oxidation of alcohols catalyzed by rhodium(III) porphyrin complexes in water: reactivity and mechanistic studies. Chem Commun. 2010;46:6353-6355.
66. Taketoshi A, Beh XN, Kuwabara J, Koizumi T, Kanbara T. Aerobic oxidative dehydrogenation of benzyl alcohols to benzaldehydes by using a cyclometalated ruthenium catalyst. Tetrahedron Lett. 2012;53:3573-3576.
67. Wang S-S, Zhang J, Zhou C-L, Vo-Thanh G, Liu Y. An ionic compound containing Ru(III)-complex cation and phosphotungstate anion as the efficient and recyclable catalyst for clean aerobic oxidation of alcohols. Catal Commun. 2012;28:152-154.
68. Borthakur R, Asthana M, Kumar A, Koch A, Lal RA. Solvent free selective oxidation of alcohols catalyzed by a trinuclear complex with a dicopper(II)-monozinc(II) centre using hydrogen peroxide as an oxidant. RSC Adv. 2013;3:22957-22962.
69. Sanmartin-Matalobos J, Garcia-Deibe AM, Briones-Miguens L, Gonzalez-Bello C, Portela-Garcia C, Fondo M. Dual role of 2-tosylaminomethylaniline as a ligand and a nucleophile in the copper-mediated oxidation of methanol. Dalton Trans. 2014;43:722-728.
70. Cao Q, Dornan LM, Rogan L, Hughes NL, Muldoon MJ. Aerobic oxidation catalysis with stable radicals. Chem Commun. 2014;50:4524-4543.
71. Tong X, Sun Y, Yan Y, Luo X, Liu J, Wu Z. Transition metal-free catalytic oxidation of aromatic alcohols with molecular oxygen in the presence of a catalytic amount of N-bromosuccinimide. J Mol Catal A Chem. 2014;391:1-6.
72. Prebil R, Stavber G, Stavber S. Aerobic oxidation of alcohols by using a completely metal-free catalytic system. Eur J Org Chem. 2014;395-402.
73. Ma X, Li Z, Liu F, Cao S, Rao H. Tetra-n-butylammonium bromide: a simple but efficient organocatalyst for alcohol oxidation under mild conditions. Adv Synth Catal. 2014;356:1741-1746.
74. Guo S, Yu J-T, Dai Q, Yang H, Cheng J. The Bu4NI-catalyzed alfa-acyloxylation of ketones with benzylic alcohols. Chem Commun. 2014;50:6240-6242.
75. Al-Hunaiti A, Räisänen M, Pihko P, Leskelä M, Repo T. Organocatalytic oxidation of secondary alcohols using 1,2-di(1-naphthyl)-1,2-ethanediamine (NEDA). Eur J Org Chem. 2014;6141-6144.
76. Rong Z-Q, Pan H-J, Yan H-L, Zhao Y. Enantioselective oxidation of 1,2-diols with quinine-derived urea organocatalyst. Org Lett. 2013;16:208-211.
77. Ciriminna R, Pagliaro M. Industrial oxidations with organocatalyst TEMPO and its derivatives. Org Process Res Dev. 2009;14:245-251.
78. Anelli PL, Biffi C, Montanari F, Quici S. Fast and selective oxidation of primary alcohols to aldehydes or to carboxylic acids and of secondary alcohols to ketones mediated by oxoammonium salts under two-phase conditions. J Org Chem. 1987;52:2559-2562.
79. Sabbatini A, Martins LMDRS, Mahmudov KT. Microwave-assisted and solventfree peroxidative oxidation of 1-phenylethanol to acetophenone with a CuII-TEMPO catalytic system. Catal Commun. 2014;48:69-72.
80. Sutradhar M, Martins LMDRS, Guedes da Silva MFC, Alegria ECBA, Liu C-M, Pombeiro AJL. Dinuclear Mn(II, II) complexes: magnetic properties and microwave assisted oxidation of alcohols. Dalton Trans. 2014;43:3966-3977
81. Alexandru M, Cazacu M, Arvinte A. μ-Chlorido-bridged dimanganese(II) complexes of the Schiff base derived from [2 +2] condensation of 2,6-diformyl-4-methylphenol and 1,3-bis(3-aminopropyl) tetramethyldisiloxane: structure, magnetism, electrochemical behaviour, and catalytic oxidation of secondary alcohols. Eur J Inorg Chem. 2014;120-131. 65. Hayashi M, Sasano Y, Nagasawa S, Shibuya M, Iwabuchi Y. 9-Azanoradamantane N-oxyl (Nor-AZADO): a highly active organocatalyst for alcohol oxidation. Chem Pharm Bull. 2011;59:1570-1573.
82. Hayashi M, Sasano Y, Nagasawa S, Shibuya M, Iwabuchi Y. 9-Azanoradamantane N-oxyl (Nor-AZADO): a highly active organocatalyst for alcohol oxidation. Chem Pharm Bull. 2011;59:1570-1573.
83. Sheldon RA, Arends IWCE. Catalytic oxidations mediated by metal ions and nitroxyl radicals. J Mol Catal A Chem. 2006;251:200-214
84. Tebben L, Studer A. Nitroxides: applications in synthesis and in polymer chemistry. Angew Chem Int Ed Engl. 2011;50:5034-5068
85. Wertz S, Studer A. Nitroxide-catalyzed transitionmetal- free aerobic oxidation processes. Green Chem. 2013;15:3116-3134
86. Ishii Y, Sakaguchi S, Iwahama T. Innovation of hydrocarbon oxidation with molecular oxygen and related reactions. Adv Synth Catal. 2001;343:393-427
87. Recupero F, Punta C. Free radical functionalization of organic compounds catalyzed by N-hydroxyphthalimide. Chem Rev. 2007;107:3800-3842
88. Coseri S. Phthalimide- N-oxyl (PINO) radical, a powerful catalytic agent: its generation and versatility towards various organic substrates. Catal Rev. 2009;51:218-292.
89. Gartshore CJ, Lupton DW. Readily accessible oxazolidine nitroxyl radicals: bifunctional cocatalysts for simplified copper based aerobic oxidation. Adv Synth Catal. 2010;352:3321-3328
90. Cheng L, Wang J, Wang M, Wu Z. Mechanistic insight into alcohol oxidation mediated by an efficient green CuII-bipy catalyst with and without TEMPO by density functional methods. Dalton Trans. 2010;39:5377-5387
91. Lu Z, Ladrak T, Roubeau O. Selective, catalytic aerobic oxidation of alcohols using CuBr2 and bifunctional triazine-based ligands containing both a bipyridine and a TEMPO group. Dalton Trans. 2009;3559-3570
92. Gamez P, Arends IWCE, Sheldon RA, Reedijk J. Room temperature aerobic copper-catalysed selective oxidation of primary alcohols to aldehydes. Adv Synth Catal. 2004;346:805-811
93. Figiel PJ, Leskelä M, Repo T. TEMPO-copper(II) diimine-catalysed oxidation of benzylic alcohols in aqueous media. Adv Synth Catal. 2007;349:1173-1179
94. Figiel PJ, Sibaouih A, Ahmad JU. Aerobic oxidation of benzylic alcohols in water by 2,2,6,6- tetramethylpiperidine-1-oxyl(TEMPO)/copper(II) 2-N-arylpyrrolecarbaldimino complexes. Adv Synth Catal. 2009;351:2625-2632
95. Salinas Uber J, Vogels Y, van den Helder D. Pyrazole-based ligands for the [copper-TEMPO]-mediated oxidation of benzyl alcohol to benzaldehyde and structures of the Cu coordination compounds. Eur J Inorg Chem. 2007;4197-4206
96. Jiang N, Ragauskas AJ. Copper(II)-catalyzed aerobic oxidation of primary alcohols to aldehydes in ionic liquid [bmpy]PF6. Org Lett. 2005;7:3689-3692
97. Striegler S. Aerobic oxidation of primary alcohols under mild aqueous conditions promoted by a dinuclear copper(II) complex. Tetrahedron. 2006;62:9109-9114
98. Mannam S, Alamsetti SK, Sekar G. Aerobic, chemoselective oxidation of alcohols to carbonyl compounds catalyzed by a DABCO-copper complex under mild conditions. Adv Synth Catal. 2007;349:2253-2258
99. Yang G, Ma J, Wang W. Heterogeneous Cu-Mn oxides mediate efficiently TEMPO-catalyzed aerobic oxidation of alcohols. Catal Lett. 2006;112:83-87
100. Yang G, Zhu W, Zhang P. Recyclable carbon supported copper-manganese oxide for selective aerobic oxidation of alcohols in combination with 2,2,6,6-tetramethylpiperidyl-1-oxyl under neutral condition. Adv Synth Catal. 2008;350:542-546
101. II complexes of arylhydrazones of active methylene nitriles. Inorg Chem. 2014;53:9946-9958.
102. Steves JE, Stahl SS. Copper(I)/ABNO-catalyzed aerobic alcohol oxidation: alleviating steric and electronic constraints of Cu/TEMPO catalyst systems. J Am Chem Soc. 2013;135:15742-15745.
103. Sasano Y, Nagasawa S, Yamazaki M, Shibuya M, Park J, Iwabuchi Y. Highly chemoselective aerobic oxidation of amino alcohols into amino carbonyl compounds. Angew Chem Int Ed Engl. 2014;53:3236-3240.
104. Wang N, Liu R, Chen J, Liang X. NaNO2-activated, iron-TEMPO catalyst system for aerobic alcohol oxidation under mild conditions. Chem Commun. 2005;42:5322-5324
105. 3/4-OH-TEMPO under mild conditions. Chin J Catal. 2008;29:935-939
106. Yin W, Chu C, Lu Q, Tao J, Liang X, Liu R. Iron chloride/ 4-acetamido-TEMPO/sodium nitrite-catalyzed aerobic oxidation of primary alcohols to the aldehydes. Adv Synth Catal. 2010;352:113-118
107. Miao C-X, Wang J-Q, Yu B. Synthesis of bimagnetic ionic liquid and application for selective aerobic oxidation of aromatic alcohols under mild conditions. Chem Commun. 2011;47:2697-2699
108. Ma S, Liu J, Li S. Development of a general and practical iron nitrate/TEMPO-catalyzed aerobic oxidation of alcohols to aldehydes/ketones: catalysis with table salt. Adv Synth Catal. 2011;353:1005-1017.
109. Cecchetto A, Fontana F, Minisci F, Recupero F. Efficient Mn-Cu and Mn-Co- TEMPO-catalysed oxidation of alcohols into aldehydes and ketones by oxygen under mild conditions. Tetrahedron Lett. 2001;42:6651-6653
110. Minisci F, Recupero F, Rodino` M, Sala M, Schneider A. A convenient nitroxyl radical catalyst for the selective oxidation of primary and secondary alcohols to aldehydes and ketones by O2 and H2O2 under mild conditions. Org Process Res Dev. 2003;7:794-798
111. Minisci F, Recupero F, Cecchetto A. Mechanisms of the aerobic oxidation of alcohols to aldehydes and ketones, catalysed under mild conditions by persistent and non-persistent nitroxyl radicals and transition metal salts-polar, enthalpic, and captodative effects. Eur J Org Chem. 2004;109-119
112. Gilhespy M, Lok M, Baucherel X. Polymersupported nitroxyl radical catalyst for selective aerobic oxidation of primary alcohols to aldehydes. Chem Commun. 2005;1085-1086
113. Gilhespy M, Lok M, Baucherel X. Polymer-supported nitroxyl radical catalysts for the hypochlorite and aerobic oxidation of alcohols. Catal Today. 2006;117:114-119.
114. Ben-Daniel R, Alsters P, Neumann R. Selective aerobic oxidation of alcohols with a combination of a polyoxometalate and nitroxyl radical as catalysts. J Org Chem. 2001;66:8650-8653.
115. Du Z, Ma J, Ma H, Wang M, Huang Y, Xu J. Vanadyl sulfate: a simple catalyst for oxidation of alcohols with molecular oxygen in combination with 2,2,6,6-tetramethylpiperidyl- 1-oxyl. Catal Commun. 2010;11:732-735.
116. Shibuya M, Osada Y, Sasano Y, Tomizawa M, Iwabuchi Y. Highly efficient, organocatalytic aerobic alcohol oxidation. J Am Chem Soc. 2011;133:6497-6500
117. Bogart JA, Lee HB, Boreen MA, Jun M, Schelter EJ. Fine-tuning the oxidative ability of persistent radicals: electrochemical and computational studies of substituted 2-pyridylhydroxylamines. J Org Chem. 2013;78:6344-6349
118. Hamada S, Furuta T, Wada Y, Kawabata T. Chemoselective oxidation by electronically tuned nitroxyl radical catalysts. Angew Chem Int Ed Engl. 2013;52:8093-8097.
119. Zhu J, Wang P, Lu M. Synthesis of novel magnetic silica supported hybrid ionic liquid combining TEMPO and polyoxometalate and its application for selective oxidation of alcohols. RSC Adv. 2012;2:8265-8268.
120. Beejapur HA, Campisciano V, Franchi P, Lucarini M, Giacalone F, Gruttadauria M. Fullerene as a platform for recyclable TEMPO organocatalysts for the oxidation of alcohols. ChemCatChem. 2014;6:2419-2424.
121. Wang L, Li J, Lv Y, Zhao G, Gao S. Selective aerobic oxidation of alcohols catalyzed by iron chloride hexahydrate/TEMPO in the presence of silica gel. Appl Organomet Chem. 2012;26:37-43.
122. Wang L, Li J, Zhao X, Lv Y, Zhang H, Gao S. An efficient and scalable room temperature aerobic alcohol oxidation catalyzed by iron chloride hexahydrate/mesoporous silica supported TEMPO. Tetrahedron. 2013;69:6041-6045.
123. Karimi B, Badreh E. SBA-15-functionalized TEMPO confined ionic liquid: an efficient catalyst system for transition-metal-free aerobic oxidation of alcohols with improved selectivity. Org Biomol Chem. 2011;9:4194-4198.
124. Obermayer D, Balu AM, Romero AA, Goessler W, Luque R, Kappe CO. Nanocatalysis in continuous flow: supported iron oxide nanoparticles for the heterogeneous aerobic oxidation of benzyl alcohol. Green Chem. 2013;15:1530-1537.
125. Ishida T, Watanabe H, Takei T, Hamasaki A, Tokunaga M, Haruta M. Metal oxidecatalyzed ammoxidation of alcohols to nitriles and promotion effect of gold nanoparticles for one-pot amide synthesis. Appl Catal A Gen. 2012;425-426:85-90.
126. 2O/TEMPO/NaCl as catalysts. Org Biomol Chem. 2013;11:4186-4193.
127. Sedai B, Díaz-Urrutia C, Baker RT, Wu R, Silks LAP, Hanson SK. Aerobic oxidation of ß-1 lignin model compounds with copper and oxovanadium catalysts. ACS Catal. 2013;3:3111-3122.
128. Painter RM, Pearson DM, Waymouth RM. Selective catalytic oxidation of glycerol to dihydroxyacetone. Angew Chem Int Ed Engl. 2010;49:9456-9459.
129. Spatareanu A, Bercea M, Budtova T, Harabagiu V, Sacarescu L, Coseri S. Synthesis, characterization and solution behaviour of oxidized pullulan. Carbohydr Polym. 2014;111:63-71.
130. Amberg M, Dönges M, Stapf G, Hartung J. Formation of 3-acyloxy-γ- butyrolactones from 4-pentenols in vanadium-catalyzed oxidations. Tetrahedron. 2014;70:5321-5331.
131. Liu J, Ma S. Iron-catalyzed aerobic oxidation of allylic alcohols: the issue of C]C bond isomerization. Org Lett. 2013;15:5150-5153.
132. 2O/TEMPO/NaCl-catalyzed aerobic oxidation of homopropargylic alcohols. Tetrahedron. 2013;69:10161-10167.
133. Ouyang X-H, Song R-J, Li J-H. Iron-catalyzed oxidative 1,2-carboacylation of activated alkenes with alcohols: a tandem route to 3-(2-oxoethyl)indolin-2-ones. Eur J Org Chem. 2014;2014:3395-3401.
134. Ben-David H, Iron MA, Neumann R. Platinum complexes of cationic ligands for the aerobic oxidation of "inert" perfluoro-substituted alcohols. Chem Commun. 2013;49:1720-1722.
135. Bowman RK, Brown AD, Cobb JH. Synthesis of HCV replicase inhibitors: basecatalyzed synthesis of protected α-hydrazino esters and selective aerobic oxidation with catalytic Pt/Bi/C for synthesis of imidazole-4,5-dicarbaldehyde. J Org Chem. 2013;78:11680-11690.
136. Duschek A, Kirsch SF. 2-Iodoxybenzoic acid-a simple oxidant with a dazzling array of potential applications. Angew Chem Int Ed Engl. 2011;50:1524-1552.
137. Satam V, Harad A, Rajule R, Pati H. 2-Iodoxybenzoic acid (IBX): an efficient hypervalent iodine reagent. Tetrahedron. 2010;66:7659-7706.
138. Uyanik M, Ishihara K. Hypervalent iodine-mediated oxidation of alcohols. Chem Commun. 2009;2086-2099.
139. Zhdankin VV. Organoiodine(V) reagents in organic synthesis. J Org Chem. 2011;76:1185-1197.
140. Thottumkara AP, Bowsher MS, Vinod TK. In situ generation of o-iodoxybenzoic acid (IBX) and the catalytic use of it in oxidation reactions in the presence of oxone as a co-oxidant. Org Lett. 2005;7:2933-2936.
141. Xu S, Itto K, Satoh M, Arimoto H. Unexpected dehomologation of primary alcohols to one-carbon shorter carboxylic acids using o-iodoxybenzoic acid (IBX). Chem Commun. 2014;50:2758-2761.
142. Li X-H, Meng X-G, Liu Y, Peng X. Direct oxidation of secondary alcohol to ester by performic acid. Green Chem. 2013;15:3332-3336.
143. Miura T, Nakashima K, Tada N, Itoh A. An effective and catalytic oxidation using recyclable fluorous IBX. Chem Commun. 2011;47:1875-1877.
144. 4: a new and mild oxidizing agent for selective oxidation of alcohols to carbonyl compounds. Tetrahedron Lett. 2012;53:4433-4435.
145. Bartlett SL, Beaudry CM. High-yielding oxidation of ß-hydroxyketones to ß-diketones using o-iodoxybenzoic acid. J Org Chem. 2011;76:9852-9855.
146. Berini C, Brayton DF, Mocka C, Navarro O. Homogeneous, anaerobic (NHeterocyclic Carbene)-Pd or -Ni catalyzed oxidation of secondary alcohols at mild temperatures. Org Lett. 2009;11:4244-4247.
147. Hamasaki A, Kuwada H, Tokunaga M. tert-Butylnitrite as a convenient and easyremovable oxidant for the conversion of benzylic alcohols to ketones and aldehydes. Tetrahedron Lett. 2012;53:811-814.
148. · Redox Pair. Org Lett. 2013;16:58-61.
149. 6-mediated selective oxidation of benzylic, allylic and propargylic alcohols. RSC Adv. 2014;4: 40561-40568.
150. Hayashi M, Shibuya M, Iwabuchi Y. Oxidation of alcohols to carbonyl compounds with diisopropyl azodicarboxylate catalyzed by nitroxyl radicals. J Org Chem. 2012;77:3005-3009.
151. Zhu Y, Zhao B, Shi Y. Highly efficient Cu(I)-catalyzed oxidation of alcohols to ketones and aldehydes with diaziridinone. Org Lett. 2013;15:992-995.
152. William JM, Kuriyama M, Onomura O. Electrochemical oxidation of 1,2-diols to α-hydroxyketones in water. Electrochemistry. 2013;81:374-376.
153. William JM, Kuriyama M, Onomura O. Boronic acid-catalyzed selective oxidation of 1,2-diols to α-hydroxy ketones in water. Adv Synth Catal. 2014;356: 934-940.
154. Nielsen M, Kammer A, Cozzula D, Junge H, Gladiali S, Beller M. Efficient hydrogen production from alcohols under mild reaction conditions. Angew Chem Int Ed Engl. 2011;50:9593-9597.
155. Baratta W, Bossi G, Putignano E, Rigo P. Pincer and diamine Ru and Os diphosphane complexes as efficient catalysts for the dehydrogenation of alcohols to ketones. Chem Eur J. 2011;17:3474-3481.
156. Prades A, Peris E, Albrecht M. Oxidations and oxidative couplings catalyzed by triazolylidene ruthenium complexes. Organometallics. 2011;30:1162-1167
157. Zhang J, Balaraman E, Leitus G, Milstein D. Electron-rich PNP- and PNN-type ruthenium(II) hydrido borohydride pincer complexes. Synthesis, structure, and catalytic dehydrogenation of alcohols and hydrogenation of esters. Organometallics. 2011;30:5716-5724
158. Shahane S, Fischmeister C, Bruneau C. Acceptorless ruthenium catalyzed dehydrogenation of alcohols to ketones and esters. Catal Sci Technol. 2012;2:1425-1428
159. Schley ND, Dobereiner GE, Crabtree RH. Oxidative synthesis of amides and pyrroles via dehydrogenative alcohol oxidation by ruthenium diphosphine diamine complexes. Organometallics. 2011;30:4174-4179.
160. Royer AM, Rauchfuss TB, Gray DL. Organoiridium pyridonates and their role in the dehydrogenation of alcohols. Organometallics. 2010;29:6763-6768
161. Musa S, Shaposhnikov I, Cohen S, Gelman D. Ligand-metal cooperation in PCP pincer complexes: rational design and catalytic activity in acceptorless dehydrogenation of alcohols. Angew Chem Int Ed Engl. 2011;50:3533-3537
162. *Ir complex having a functional C,N-chelate ligand. Org Lett. 2011;13:2278-2281
163. *Ir catalysts bearing a functional bipyridine ligand. J Am Chem Soc. 2012;134:3643-3646
164. Kawahara R, Fujita K, Yamaguchi R. Cooperative catalysis by iridiumcomplexes with a bipyridonate ligand: versatile dehydrogenative oxidation of alcohols and reversible dehydrogenation-hydrogenation between 2-propanol and acetone. Angew Chem Int Ed Engl. 2012;51:12790-12794
165. Polukeev AV, Petrovskii PV, Peregudov AS, Ezernitskaya MG, Koridze AA. Dehydrogenation of alcohols by bis(phosphinite) benzene based and bis(phosphine) ruthenocene based iridium pincer complexes. Organometallics. 2013;32(4):1000-1015.
166. *Ir complex in aqueous solution. New J Chem. 2014; 38:3862-3873.
167. Zeng G, Sakaki S, Fujita K, Sano H, Yamaguchi R. Efficient catalyst for acceptorless alcohol dehydrogenation: interplay of theoretical and experimental studies. ACS Catal. 2014;4(3):1010-1020.
168. Aliende C, Pérez-Manrique M, Jalón FA, Manzano BR, Rodríguez AM, Espino G. Arene ruthenium complexes as versatile catalysts in water in both transfer hydrogenation of ketones and oxidation of alcohols. Selective deuterium labeling of rac-1- phenylethanol. Organometallics. 2012;31:6106-6123.
169. Musa S, Ackermann L, Gelman D. Dehydrogenative cross-coupling of primary and secondary alcohols. Adv Synth Catal. 2013;355:3077-3080.
170. Yang J, Liu X, Meng D-L. Efficient iron-catalyzed direct ß-alkylation of secondary alcohols with primary alcohols. Adv Synth Catal. 2012;354:328-334.
171. Xu C, Goh LY, Pullarkat SA. Efficient iridium-thioether-dithiolate catalyst for ß-alkylation of alcohols and selective imine formation via N-alkylation reactions. Organometallics. 2011;30:6499-6502.
172. Miura T, Kose O, Li F, Kai S, Saito S. CuI/H2/NaOHcatalyzed cross-coupling of two different alcohols for carbon-carbon bond formation: "borrowing hydrogen"? Chem Eur J. 2011;17:11146-11151.
173. Kose O, Saito S. Cross-coupling reaction of alcohols for carbon-carbon bond formation using pincer-type NHC/palladium catalysts. Org Biomol Chem. 2010;8:896-900.
174. Gnanamgari D, Sauer ELO, Schley ND, Butler C, Incarvito CD, Crabtree RH. Iridium and ruthenium complexes with chelating N-heterocyclic carbenes: efficient catalysts for transfer hydrogenation, ß-alkylation of alcohols, and N-alkylation of amines. Organometallics. 2008;28:321-325.
175. Shimizu K, Sato R, Satsuma A. Direct C-C cross-coupling of secondary and primary alcohols catalyzed by a γ-alumina-supported silver subnanocluster. Angew Chem Int Ed Engl. 2009;121:4042-4046.
176. Shimizu K, Sato R, Satsuma A. Direct C-C cross-coupling of secondary and primary alcohols catalyzed by a γ-alumina-supported silver subnanocluster. Angew Chem Int Ed Engl. 2009;48:3982-3986.
177. Zhang G, Hanson SK. Cobalt-catalyzed acceptorless alcohol dehydrogenation: synthesis of imines from alcohols and amines. Org Lett. 2013;15:650-653.
178. Zhang G, Vasudevan KV, Scott BL, Hanson SK. Understanding the mechanisms of cobalt-catalyzed hydrogenation and dehydrogenation reactions. J Am Chem Soc. 2013;135:8668-8681.
179. Kamitani M, Ito M, Itazaki M, Nakazawa H. Effective dehydrogenation of 2-pyridylmethanol derivatives catalyzed by an iron complex. Chem Commun. 2014;50:7941-7944.
180. Kirillov AM, Shul'pin GB. Pyrazinecarboxylic acid and analogs: highly efficient co-catalysts in the metal-complex-catalyzed oxidation of organic compounds. Coord Chem Rev. 2013;257:732-754.
181. Song H, Kang B, Hong SH. Fe-catalyzed acceptorless dehydrogenation of secondary benzylic alcohols. ACS Catal. 2014;4:2889-2895.
182. Mitsudome T, Mikami Y, Funai H, Mizugaki T, Jitsukawa K, Kaneda K. Oxidantfree alcohol dehydrogenation using a reusable hydrotalcite-supported silver nanoparticle catalyst. Angew Chem Int Ed Engl. 2008;47:138-141.
183. Fang W, Zhang Q, Chen J, Deng W, Wang Y. Gold nanoparticles on hydrotalcites as efficient catalysts for oxidantfree dehydrogenation of alcohols. Chem Commun. 2010;46:1547-1549.
184. Zhang Q, Deng W, Wang Y. Effect of size of catalytically active phases in the dehydrogenation of alcohols and the challenging selective oxidation of hydrocarbons. Chem Commun. 2011;47:9275-9292.
185. Fang W, Chen J, Zhang Q, Deng W, Wang Y. Hydrotalcitesupported gold catalyst for the oxidant-free dehydrogenation of benzyl alcohol: studies on support and gold size effects. Chem Eur J. 2011;17:1247-1256.
186. Chen J, Fang W, Zhang Q, Deng W, Wang Y. A comparative study of size effects in the Au-catalyzed oxidative and non-oxidative dehydrogenation of benzyl alcohol. Chem Asian J. 2014;9:2187-2196.
187. Yi J, Miller JT, Zemlyanov DY. A reusable unsupported rhenium nanocrystalline catalyst for acceptorless dehydrogenation of alcohols through γ-C-H activation. Angew Chem Int Ed Engl. 2014;53:833-836.
188. Sawama Y, Morita K, Yamada T. Rhodium-on-carbon catalyzed hydrogen scavengerand oxidant-free dehydrogenation of alcohols in aqueous media. Green Chem. 2014;16:3439-3443.
189. Kon K, Hakim Siddiki SMA, Shimizu K. Size- and support-dependent Pt nanocluster catalysis for oxidant-free dehydrogenation of alcohols. J Catal. 2013;304:63-71.
190. Shimizu K, Kon K, Shimura K, Hakim SSMA. Acceptor-free dehydrogenation of secondary alcohols by heterogeneous cooperative catalysis between Ni nanoparticles and acid-base sites of alumina supports. J Catal. 2013;300:242-250.
191. Damodara D, Arundhathi R, Likhar PR. Copper nanoparticles from copper aluminum hydrotalcite: an efficient catalyst for acceptor- and oxidant-free dehydrogenation of amines and alcohols. Adv Synth Catal. 2014;356:189-198.
192. Shimizu K, Kon K, Seto M, Shimura K, Yamazaki H, Kondo JN. Heterogeneous cobalt catalysts for the acceptorless dehydrogenation of alcohols. Green Chem. 2013;15:418-424.
193. Li F, Sun C, Wang N. Catalytic acceptorless dehydrogenative coupling of arylhydrazines and alcohols for the synthesis of arylhydrazones. J Org Chem. 2014;79:8031-8039.
194. Fujita K, Ito W, Yamaguchi R. Dehydrogenative lactonization of diols in aqueous media catalyzed by a water-soluble iridium complex bearing a functional bipyridine ligand. ChemCatChem. 2014;6:109-112.
195. Balaraman E, Khaskin E, Leitus G, Milstein D. Catalytic transformation of alcohols to carboxylic acid salts and H2 using water as the oxygen atom source. Nat Chem. 2013;5:122-125.
196. Gnanaprakasam B, Milstein D. Synthesis of amides from esters and amines with liberation of H2 under neutral conditions. J Am Chem Soc. 2011;133:1682-1685
197. Gnanaprakasam B, Ben-David Y, Milstein D. Ruthenium pincer-catalyzed acylation of alcohols using esters with liberation of hydrogen under neutral conditions. Adv Synth Catal. 2010;352:3169-3173.
198. Balaraman E, Gnanaprakasam B, Shimon LJW, Milstein D. Direct hydrogenation of amides to alcohols and amines under mild conditions. J Am Chem Soc. 2010;132:16756-16758
199. Gunanathan C, Ben-David Y, Milstein D. Direct synthesis of amides from alcohols and amines with liberation of H2. Science. 2007;317:790-792
200. Zhang J, Leitus G, Ben-David Y, Milstein D. Facile conversion of alcohols into esters and dihydrogen catalyzed by new ruthenium complexes. J Am Chem Soc. 2005;127:10840-10841.
201. Gunanathan C, Milstein D. Metal-ligand cooperation by aromatization-dearomatization: a new paradigm in bond activation and "Green" catalysis. Acc Chem Res. 2011;44:588-602.
202. Li H, Hall MB. Mechanism of the formation of carboxylate from alcohols and water catalyzed by a bipyridine-based ruthenium complex: a computational study. J Am Chem Soc. 2013;136:383-395.
203. Bartoszewicz A, Ahlsten N, Martín-Matute B. Enantioselective synthesis of alcohols and amines by iridium-catalyzed hydrogenation, transfer hydrogenation, and related processes. Chem Eur J. 2013;19:7274-7302.
204. Arita S, Koike T, Kayaki Y, Ikariya T. Aerobic oxidative kinetic resolution of racemic secondary alcohols with chiral bifunctional amido complexes. Angew Chem Int Ed Engl. 2008;47:2447-2449.
205. 2. RSC Adv. 2013;3:19247-19250.
206. Bettucci L, Bianchini C, Filippi J, Lavacchi A, Oberhauser W. Chemoselective aerobic diol oxidation by palladium(II)-pyridine catalysis. Eur J Inorg Chem. 2011;1797-1805.
207. Bettucci L, Bianchini C, Oberhauser W, Hsiao T-H, Lee HM. Chemoselective aerobic oxidation of unprotected diols catalyzed by Pd-(NHC) (NHC1/4N-heterocyclic carbene) complexes. J Mol Catal A Chem. 2010;322:63-72.
208. De Crisci AG, Chung K, Oliver AG, Solis-Ibarra D, Waymouth RM. Chemoselective oxidation of polyols with chiral palladium catalysts. Organometallics. 2013;32:2257-2266.
209. Chung K, Banik SM, De Crisci AG. Chemoselective Pd-catalyzed oxidation of polyols: synthetic scope and mechanistic studies. J Am Chem Soc. 2013;135:7593-7602.
210. Ebner DC, Bagdanoff JT, Ferreira EM. The palladium-catalyzed aerobic kinetic resolution of secondary alcohols: reaction development, scope, and applications. Chem Eur J. 2009;15:12978-12992.
211. Suzuki T, Morita K, Matsuo Y, Hiroi K. Catalytic asymmetric oxidative lactonizations of meso-diols using a chiral iridium complex. Tetrahedron Lett. 2003;44: 2003-2006.
212. Moritani J, Hasegawa Y, Kayaki Y, Ikariya T. Aerobic oxidative desymmetrization of meso-diols with bifunctional amidoiridium catalysts bearing chiral N-sulfonyldiamine ligands. Tetrahedron Lett. 2014;55:1188-1191.
213. Manzini S, Urbina-Blanco CA, Nolan SP. Chemoselective oxidation of secondary alcohols using a ruthenium phenylindenyl complex. Organometallics. 2013;32:660-664.
214. Mizoguchi H, Uchida T, Katsuki T. Ruthenium-catalyzed oxidative kinetic resolution of unactivated and activated secondary alcohols with air as the hydrogen acceptor at room temperature. Angew Chem Int Ed Engl. 2014;53:3178-3182.
215. Onomura O, Arimoto H, Matsumura Y, Demizu Y. Asymmetric oxidation of 1,2- diols using N-bromosuccinimide in the presence of chiral copper catalyst. Tetrahedron Lett. 2007;48:8668-8672.
216. 0 systems. Chem Eur J. 2010;16:6857-6860.
217. Zhang Y, Zhou Q, Ma W, Zhao J. Enantioselective oxidation of racemic secondary alcohols catalyzed by chiral Mn(III)-salen complex with sodium hypochlorite as oxidant. Catal Commun. 2014;45:114-117.
218. Bera PK, Maity NC, Abdi SHR, Khan N-uH, Kureshy RI, Bajaj HC. Macrocyclic Mn(III) salen complexes as recyclable catalyst for oxidative kinetic resolution of secondary alcohols. Appl Catal A Gen. 2013;467:542-551.
219. Willemsen JS, van Hest JCM, Rutjes FPJT. Potassium formate as a small molecule switch: controlling oxidation-reduction behaviour in a two-step sequence. Chem Commun. 2013;49:3143-3145.
220. Hamid MHSA, Slatford PA, Williams JMJ. Borrowing hydrogen in the activation of alcohols. Adv Synth Catal. 2007;349:1555-1575.
221. Liu Q, Wu L, Gülak S, Rockstroh N, Jackstell R, Beller M. Towards a sustainable synthesis of formate salts: combined catalytic methanol dehydrogenation and bicarbonate hydrogenation. Angew Chem Int Ed Engl. 2014;53:7085-7088.
222. Moromi SK, Siddiki HSMA, Ali MA, Kon K, Shimizu K. Acceptorless dehydrogenative coupling of primary alcohols to esters by heterogeneous Pt catalysts. Catal Sci Technol. 2014;4:3631-3635.
223. Azizi K, Karimi M, Nikbakht F, Heydari A. Direct oxidative amidation of benzyl alcohols using EDTA@Cu(II) functionalized superparamagnetic nanoparticles. Appl Catal A Gen. 2014;482:336-343.
224. Fries P, Halter D, Kleinschek A, Hartung J. Functionalized tetrahydrofurans from alkenols and olefins/alkynes via aerobic oxidation-radical addition cascades. J Am Chem Soc. 2011;133:3906-3912.
225. 4 photocatalyst under visible light irradiation. Appl Catal B Environ. 2014;158-159:382-390.
226. Saito T, Isogai A. TEMPO-mediated oxidation of native cellulose. The effect of oxidation conditions on chemical and crystal structures of the water-insoluble fractions. Biomacromolecules. 2004;5:1983-1989.
227. Wolfel R, Taccardi N, Bosmann A, Wasserscheid P. Selective catalytic conversion of biobased carbohydrates to formic acid using molecular oxygen. Green Chem. 2011;13:2759-2763.
228. Zhang J, Sun M, Liu X, Han Y. Catalytic oxidative conversion of cellulosic biomass to formic acid and acetic acid with exceptionally high yields. Catal Today. 2014; 233:77-82.
229. Fellay C, Dyson PJ, Laurenczy G. A viable hydrogen-storage system based on selective formic acid decomposition with a ruthenium catalyst. Angew Chem Int Ed Engl. 2008;47:3966-3968.
230. Boddien A, Loges B, Gartner F, et al. Iron-catalyzed hydrogen production from formic acid. J Am Chem Soc. 2010;132:8924-8934.
231. Weingarten R, Conner WC, Huber GW. Production of levulinic acid from cellulose by hydrothermal decomposition combined with aqueous phase dehydration with a solid acid catalyst. Energy Environ Sci. 2012;5:7559-7574.
232. Van de Vyver S, Thomas J, Geboers J, et al. Catalytic production of levulinic acid from cellulose and other biomass-derived carbohydrates with sulfonated hyperbranched poly(arylene oxindole)s. Energy Environ Sci. 2011;4:3601-3610.
233. Fukuoka A, Dhepe PL. Catalytic conversion of cellulose into sugar alcohols. Angew Chem Int Ed Engl. 2006;45:5161-5163.
234. Ji N, Zhang T, Zheng MY, et al. Direct catalytic conversion of cellulose into ethylene glycol using nickel-promoted tungsten carbide catalysts. Angew Chem Int Ed Engl. 2008;47:8510-8513.
235. Holm MS, Saravanamurugan S, Taarning E. Conversion of sugars to lactic acid derivatives using heterogeneous zeotype catalysts. Science. 2010;328:602-605.
236. Zhang JZ, Liu X, Sun M, Ma XH, Han Y. Direct conversion of cellulose to glycolic acid with a phosphomolybdic acid catalyst in a water medium. ACS Catal. 2012;2:1698-1702.
237. 40 nanocomposite catalyst. ChemCatChem. 2011;3:1294-1298.
238. Carrettin S, McMorn P, Johnston P, Griffin K, Hutchings GJ. Selective oxidation of glycerol to glyceric acid using a gold catalyst in aqueous sodium hydroxide. Chem Commun. 2002;696-697.
239. Brett L, He Q, Hammond C, et al. Selective oxidation of glycerol by highly active bimetallic catalysts at ambient temperature under base-free conditions. Angew Chem Int Ed Engl. 2011;50:10136-10139.
240. Zhang Y, Zhao G, Zhang Y, Huang X. Highly efficient visible-light-driven photoelectro-catalytic selective aerobic oxidation of biomass alcohols to aldehydes. Green Chem. 2014;16:3860-3869.
241. Beauchamp J, Gross PG, Vieille C. Characterization of Thermotoga Maritima glycerol dehydrogenase for the enzymatic production of dihydroxyacetone. Appl Microbiol Biotechnol. 2014;98:7039-7050.
242. Ojeda M, Balu AM, Romero AA, et al. MAGBONS: novel magnetically separable carbonaceous nanohybrids from porous polysaccharides. ChemCatChem. 2014;6:2847-2853.
243. Davis SE, Houk LR, Tamargo EC, Datye AK, Davis RJ. Oxidation of 5-hydroxymethylfurfural over supported Pt, Pd and Au catalysts. Catal Today. 2011;160:55-60.
244. Villa A, Schiavoni M, Campisi S, Veith GM, Prati L. Pd-modified Au on carbon as an effective and durable catalyst for the direct oxidation of HMF to 2,5-furandicarboxylic acid. ChemSusChem. 2013;6:609-612.
245. Ni M, Leung DYC, Leung MKH. A review on reforming bio-ethanol for hydrogen production. Int J Hydrog Energy. 2007;32:3238-3247.
246. Nielsen M, Alberico E, Baumann W, et al. Low-temperature aqueous-phase methanol dehydrogenation to hydrogen and carbon dioxide. Nature. 2013;495:85-89.
247. 3 catalyst for hydrogen production by crude bioethanol steam reforming. Int J Hydrog Energy. 2011;36:311-318.
248. Duprez D. Selective steam reforming of aromatic compounds on metal-catalysts. Appl Catal A Gen. 1992;82:111-157.
249. 3. Int J Hydrog Energy. 2012;37:4955-4966.
250. Qu YC, Wei XL, Zuo Y, et al. A novel catalyst-free process for producing hydrogen and carboxylate from biomass-derived alcohols. Int J Hydrog Energy. 2014;39:13136-13140.
251. Herrero MA, Kremsner JM, Kappe CO. Nonthermal microwave effects revisited: on the importance of internal temperature monitoring and agitation in microwave chemistry. J Org Chem. 2007;73:36-47.
252. Obermayer D, Kappe CO. On the importance of simultaneous infrared/fiber-optic temperature monitoring in the microwave-assisted synthesis of ionic liquids. Org Biomol Chem. 2010;8:114-121
253. Kappe CO. Controlled microwave heating in modern organic synthesis. Angew Chem Int Ed Engl. 2004;43:6250-6284
254. Hoz A, Diaz-Ortiz A, Moreno A. Microwaves in organic synthesis. Thermal and non-thermalmicrowave effects. Chem Soc Rev. 2005;34:164-178.
255. Farra`s P, Maji S, Benet-Buchholz J, Llobet A. Synthesis, characterization, and reactivity of dyad ruthenium-based molecules for light-driven oxidation catalysis. Chem Eur J. 2013;19:7162-7172
256. Ohzu S, Ishizuka T, Hirai Y, Fukuzumi S, Kojima T. Photocatalytic oxidation of organic compounds in water by using ruthenium(ii)- pyridylamine complexes as catalysts with high efficiency and selectivity. Chem Eur J. 2013;19:1563-1567
257. Guillo P, Hamelin O, Batat P, Jonusauskas G, McClenaghan ND, Menage S. Photocatalyzed sulfide oxygenation with water as the unique oxygen atom source. Inorg Chem. 2012;51:2222-2230.
258. Bellardita M, Loddo V, Palmisano G, Pibiri I, Palmisano L, Augugliaro V. Photocatalytic green synthesis of piperonal in aqueous TiO2 suspension. Appl Catal B Environ. 2014;144:607-613.
259. Palmisano G, García-López E, Marcí G, et al. Advances in selective conversions by heterogeneous photocatalysis. Chem Commun. 2010;46:7074-7089
260. Augugliaro V, Palmisano L. Green oxidation of alcohols to carbonyl compounds by heterogeneous photocatalysis. ChemSusChem. 2010;3:1135-1138
261. Yurdakal S, Palmisano G, Loddo V, Alagoz O, Augugliaro V, Palmisano L. Selective photocatalytic oxidation of 4-substituted aromatic alcohols in water with rutile TiO2 prepared at room temperature. Green Chem. 2009;11:510-516.
262. 2 supported on titanium anodes. Appl Catal B Environ. 2013;132-133:535-542.
263. 2 photocatalysts supported on phosphors for the selective photocatalytic oxidation of ethanol to acetaldehyde. Catal Today. 2013;205:159-167.
264. 2. Molecules. 2014;19:17279-17304.
265. Spasiano D, Marotta R, Di Somma I, Andreozzi R, Caprio V. Fe(III)-photocatalytic partial oxidation of benzyl alcohol to benzaldehyde under UV-solar simulated radiation. Photochem Photobiol Sci. 2013;12:1991-2000.
266. 2-mediated zirconium metal-organic framework as an efficient visible-light-driven photocatalyst for selective oxidation of alcohols and reduction of aqueous Cr(VI). Dalton Trans. 2013; 42:13649-13657.
267. Gassama A, Hoffmann N. Selective light supported oxidation of hexoses using air as oxidant-synthesis of tetrahydroxyazepanes. Adv Synth Catal. 2008; 350:35-39.
268. Hallett-Tapley GL, Silvero MJ, Gonzílez-Béjar M, Grenier M, Netto-Ferreira JC, Scaiano JC. Plasmon-mediated catalytic oxidation of sec-phenethyl and benzyl alcohols. J Phys Chem C. 2011;115:10784-10790.
269. Wannberg J, Wallinder C, Ünlüsoy M, Sköld C, Larhed MJ. One-pot, two-step, microwave-assisted palladium-catalyzed conversion of aryl alcohols to aryl fluorides via aryl nonaflates. Org Chem. 2013;78:4184-4189.
270. Takahashi M, Oshima K, Matsubara S. Hydrogen transfer type oxidation of alcohols by rhodium and ruthenium catalyst under microwave irradiation. Tetrahedron Lett. 2003;44:9201-9203.
271. Figiel PJ, Kopylovich MN, Lasri J, da Silva MFC G, da Silva JJR F, Pombeiro AJL. Solvent-free microwave-assisted peroxidative oxidation of secondary alcohols to the corresponding ketones catalyzed by copper(II) 2,4-alkoxy-1,3,5-triazapentadienato complexes. Chem Commun. 2010;46:2766-2768
272. Kopylovich MN, YaYu Karabach, da Silva MFC Guedes, Figiel PJ, Lasri J, Pombeiro AJL. Alkoxy-1,3,5-triazapentadien (e/ato) copper(II) complexes: template formation and applications for the preparation of pyrimidines and as catalysts for oxidation of alcohols to carbonyl products. Chem Eur J. 2012;18:899-914.
273. Montagut-Romans A, Boulven M, Lemaire M, Popowycz F. Efficient C-3 reductive alkylation of 4-hydroxycoumarin by dehydrogenative oxidation of benzylic alcohols through ruthenium catalysis. New J Chem. 2014;38:1794-1801.
274. Bekhradnia AR, Arshadi S. Efficient selective oxidation of organic substrates using pyridinum sulfonate halochromate under solvent-free conditions and microwave irradiation: experimental and theoretical study. Synth React Inorg Met-Org Nano-Met Chem. 2012;42:705-710.
275. 3(cat.)/TBHP under MWI. Chin Chem Lett. 2011;22:268-271.
276. Galica M, Kasprzyk W, Bednarz S, Bogda D. Microwave-assisted oxidation of alcohols by hydrogen peroxide catalysed by tetrabutylammonium decatungstate. Chem Pap. 2013;67:1240-1244.
277. Landers B, Berini C, Wang C, Navarro O. (N-heterocyclic carbene)-Pd-catalyzed anaerobic oxidation of secondary alcohols and domino oxidation-arylation reactions. J Org Chem. 2011;76:1390-1397.
278. Winkelmann OH, Navarro O. Microwave-assisted synthesis of N-heterocyclic carbene-palladium(II) complexes. Adv Synth Catal. 2010;352:212-214.
279. Landers B, Navarro O. Microwave-assisted synthesis of (N-heterocyclic carbene) Ni(Cp)Cl complexes. Inorg Chim Acta. 2012;380:350-353.
280. 2 by synergic effect of ionic liquid and microwave: chemoselective oxidation of benzylic alcohols to carbonyls and unexpected formation of anthraquinone in aqueous conditions. Mol Divers. 2011;15:687-695.
281. Rajabi F, Balu AM, Toreinia F, Luque R. A versatile supported cobalt(II) complex for heterogeneously catalysed processes: conventional vs. microwave irradiation protocols. Catal Sci Technol. 2011;1:1051-1059.
282. 4 nanoferrite as a novel catalyst for selective oxidation of benzyl alcohol to benzaldehyde. Main Group Chem. 2013;12:177-184.
283. Suslick KS, Price GJ. Applications of ultrasound to materials chemistry. Annu Rev Mater Sci. 1999;29:295-326.
284. Chakraborty V, Bordoloi M. Microwave-assisted oxidation of alcohols by pyridinium chlorochromate. J Chem Res. 1999;2:118-119.
285. Chatel G, Monnier C, Kardos N, Voiro C, Andrioletti B, Draye M. Green, selective and swift oxidation of cyclic alcohols to corresponding ketones. Appl Catal A Gen. 2014;478:157-164.
286. Matuszek K, Zawadzk P, Czardybon W, Chrobok A. New strategies for the synthesis of lactones using peroxymonosulphate salts, ionic liquids and microwave or ultrasound irradiation. New J Chem. 2014;38:237-241.
287. Beier MJ, Hansen TW, Grunwaldt JD. Selective liquid-phase oxidation of alcohols catalyzed by a silver-based catalyst promoted by the presence of ceria. J Catal. 2009;266:320-330.
288. Zhu J, Faria JL, Figueiredo JL, Thomas A. Reaction mechanism of aerobic oxidation of alcohols conducted on activated-carbon-supported cobalt oxide catalysts. Chem Eur J. 2011;17:7112-7117.
289. Sankar M, Nowicka E, Tiruvalam R, et al. Controlling the duality of the mechanism in liquid-phase oxidation of benzyl alcohol catalysed by supported Au-Pd nanoparticles. Chem Eur J. 2011;17:6524-6532.
290. Villa A, Wang D, Su DS, Prati L. New challenges in gold catalysis: bimetallic systems. Catal Sci Technol. 2015;5:55-68.
291. Farsani MR, Yadollahi B. Synthesis, characterization and catalytic performance of a Fe polyoxometalate/silica composite in the oxidation of alcohols with hydrogen peroxide. J Mol Catal A Chem. 2014;392:8-15.
292. Chorghade R, Battilocchio C, Hawkins JM, Ley SV. Sustainable flow Oppenauer oxidation of secondary benzylic alcohols with a heterogeneous zirconia catalyst. Org Lett. 2013;15:5698-5701.
293. 2 catalysts for eco-friendly oxidation of benzyl alcohol. J Ind Eng Chem. 2014;20:3115-3121.
294. Corberán VC, Gómez-Avilésa A, Martínez-Gonzáleza S, Ivanovab S, Domínguez MI, González-Péreza ME. Heterogeneous selective oxidation of fatty alcohols: oxidation of 1-tetradecanol as a model substrate. Catal Today. 2014;238:49-53.
295. Tongsakul D, Nishimura S, Ebitani K. Platinum/gold alloy nanoparticles-supported hydrotalcite catalyst for selective aerobic oxidation of polyols in base-free aqueous solution at room temperature. ACS Catal. 2013;3:2199-2207.
296. Mahdavi V, Hasheminasab HR. Vanadium phosphorus oxide catalyst promoted by cobalt doping for mild oxidation of benzyl alcohol to benzaldehyde in the liquid phase. Appl Catal A Gen. 2014;482:189-197.
297. Ozawa M, Fukutome A, Sannami Y, Kamitakahara H, Takano T. Preparation and evaluation of the oxidation ability of hematin-appended 6-amino-6-deoxycellulose. J Wood Chem Technol. 2014;34:262-272.
298. 2. Mater Res Bull. 2014;57:210-220.
299. Patel A, Singh S. Undecatungstophosphate anchored to MCM-41: an ecofriendly and efficient bifunctional solid catalyst for non-solvent liquid-phase oxidation as well as esterification of benzyl alcohol. Microporous Mesoporous Mater. 2014;195:240-249.
300. Kim YH, Hwang SK, Kim JW, Lee YS. Zirconia-supported ruthenium catalyst for efficient aerobic oxidation of alcohols to aldehydes. Ind Eng Chem Res. 2014; 53:12548-12552.
301. Parlett CMA, Keshwalla P, Wainwright SG, et al. Hierarchically ordered nanoporous Pd/SBA-15 catalyst for the aerobic selective oxidation of sterically challenging allylic alcohols. ACS Catal. 2013;3:2122-2129.
302. Parlett CMA, Bruce DW, Hondow NS, Newton MA, Lee AF, Wilson K. Mesoporous silicas as versatile supports to tune the palladium-catalyzed selective aerobic oxidation of allylic alcohols. ChemCatChem. 2013;5:939-950.
303. Mahyari M, Laeini MS, Shaabani A. Aqueous aerobic oxidation of alkyl arenes and alcohols catalyzed by copper(II) phthalocyanine supported on three-dimensional nitrogen-doped graphene at room temperature. Chem Commun. 2014;50:7855-7857.
304. 2. Catal Lett. 2014;144:1450-1459.
305. Rezaei B, Havakeshian E, Ensafi AA. Fabrication of a porous Pd film on nanoporous stainless steel using galvanic replacement as a novel electrocatalyst/electrode design for glycerol oxidation. Electrochim Acta. 2014;136:89-96.
306. Qiao ZA, Zhang P, Chai SH, et al. Lab-in-a-shell: encapsulating metal clusters for size sieving catalysis. J Am Chem Soc. 2014;136:11260-11263.
307. Yan Y, Chen Y, Jia X, Yang Y. Palladium nanoparticles supported on organosilanefunctionalized carbon nanotube for solvent-free aerobic oxidation of benzyl alcohol. Appl Catal B Environ. 2014;156-157:385-397.
308. Ishida T, Onumab Y, Kinjo K, et al. Preparation of microporous polymer-encapsulated Pd nanoparticles and their catalytic performance for hydrogenation and oxidation. Tetrahedron. 2014;70:6150-6155.
309. Gil S, Jiménez-Borja C, Martin-Campo J, Romero A, Valverde JL, Sánchez-Silva L. Stabilizer effects on the synthesis of gold-containing microparticles. Application to the liquid phase oxidation of glycerol. J Colloid Interface Sci. 2014;431:105-111.
310. Mahyari M, Shaabani A, Behbahani M, Bagheri A. Thiol-functionalized fructosederived nanoporous carbon as a support for gold nanoparticles and its application for aerobic oxidation of alcohols in water. Appl Organomet Chem. 2014;28:576-583.
311. Parvulescu VI, Hardacre C. Catalysis in ionic liquids. Chem Rev. 2007;107:2615-2665.
312. Han X, Poliakoff M. Continuous reactions in supercritical carbon dioxide: problems, solutions and possible ways forward. Chem Soc Rev. 2012;41:1428-1436.
313. Fall A, Sene M, Gaye M, Gomez G, Fall Y. Ionic liquid-supported TEMPO as catalyst in the oxidation of alcohols to aldehydes and ketones. Tetrahedron Lett. 2010; 51:4501-4504.
314. 2. ChemCatChem. 2011;3:1208-1213.
315. Zhang Y, Lu F, Cao X, Zhao J. Deep eutectic solvent supported TEMPO for oxidation of alcohols. RSC Adv. 2014;4:40161-40169.
316. 2]): an efficient and reusable catalytic system for solvent-free aerobic oxidation of alcohols. New J Chem. 2014;38:4149-4154.
317. Movahed SK, Lehi NF, Dabiri M. Gold nanoparticle supported on ionic liquid modified graphene oxide as an efficient and recyclable catalyst for one-pot oxidative A3-coupling reaction of benzyl alcohols. RSC Adv. 2014;4:42155-42158.
318. 3] with humic acid under microwave irradiation and its application as a nanocatalyst. Asian J Chem. 2013;25:9949-9995.
319. Li Z, Gong H, Mu T, Luan Y. Ionic liquid-assisted synthesis of unusual Pd particles with enhanced electrocatalytic performance for ethanol and methanol oxidation. CrystEngComm. 2014;16:4038-4044.
320. Dileep R, Bhat BR, Kumara THS. Palladium complex in a room temperature ionic liquid: a convenient recyclable reagent for catalytic oxidation. Green Chem Lett Rev. 2014;7:32-36.
321. Chepaikin EG, Bezruchko AP, Menchikova GN, Moiseeva NI, Gekhman AE. Direct catalytic oxidation of lower alkanes in ionic liquid media. Pet Chem. 2014; 545:374-381.
322. Chen L, Zhou T, Chen L, et al. Selective oxidation of cyclohexanol to cyclohexanone in the ionic liquid 1-octyl-3-methylimidazolium chloride. Chem Commun. 2011; 47:9354-9356.
323. Saluja P, Magoo D, Khurana JM. Lanthanum triflate-catalyzed rapid oxidation of secondary alcohols using hydrogen peroxide urea adduct (UHP) in ionic liquid. Synth Commun. 2014;44:800-806.
324. Paul CE, Lavandera I, Gotor-Fernandez V, Gotor V. Imidazolium-based ionic liquids as non-conventional media for alcohol dehydrogenase-catalysed reactions. Top Catal. 2014;57:332-338.
325. Fan H, Yang Y, Song J, et al. One-pot sequential oxidation and aldol condensation reactions of veratryl alcohol catalyzed by the Ru@ZIF-8+CuO/basic ionic liquid system. Green Chem. 2014;16:600-604.
326. Schneider MS, Baiker A. Aerogels in catalysis. Catal Rev Sci Eng. 1995;37:515-556.
327. 2: a beneficial medium for heterogeneously catalyzed oxidation reactions. Appl Catal A Gen. 2006; 50:298-303.
328. 4 nanoparticles as an efficient catalyst for the oxidation of alcohols to carbonyl compounds in the presence of oxone as an oxidant. Bull Kor Chem Soc. 2014;35:2029-2032.
329. Ito Y, Ohta H, Yamada YMA, Enoki T, Uozumi Y. Bimetallic Co-Pd alloy nanoparticles as magnetically recoverable catalysts for the aerobic oxidation of alcohols in water. Tetrahedron. 2014;70:6146-6149.
330. Vinod CP, Wilson K, Lee AF. Recent advances in the heterogeneously catalysed aerobic selective oxidation of alcohols. J Chem Technol Biotechnol. 2011;86:161-171.