Novel organocatalytic system for the oxidation of primary aliphatic alcohols to dimeric esters using oxygen

Oxidation Communications

Volumn 33, Issue 2, 2010, Pages 274-282

  Sheng, X ^a,b   Ma, H ^a   Gao, J ^a   Du, Z H ^a,b   Xu, J ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

2,4,4,6 tetrabromo 2; 5 cyclohexadienone; Dimeric ester; Organocatalytic system; Oxygen; Primary aliphatic alcohol

Indexed keywords

EID: 77954893243     PISSN: 02094541     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. 2- activated, Iron-TEMPO Catalyst System for Aerobic Alcohol Oxidation under Mild Conditions. Chem. Commun., 42, 5322 (2005).
2. B. Z. ZHAN, A. THOMPSON: Recent Developments in the Aerobic Oxidation of Alcohols. Tetrahedron, 60, 2917 (2004).
3. R. A. SHELDON, I. ARENDS: Organocatalytic Oxidations Mediated by Nitroxyl Radicals. Adv. Synth. Catal., 346, 1051 (2004).
4. K. MORI, T. HARA, T. MIZUGAKI, K. EBITANI, K. KANEDA: Hydroxyapatite-supported Palladium Nanoclusters: A Highly Active Heterogeneous Catalyst for Selective Oxidation of Alcohols by Use of Molecular Oxygen. J. Am. Chem. Soc., 126, 10657 (2004).
5. H. TOHMA, T. MAEGAWA, Y. KITA: Facile and Efficient Oxidative Transformation of Primary Alcohols to Methyl Esters in Water Using Hypervalent Iodine(III) Reagents. Synlett, 5, 72 (2003).
6. G. A. HIEGEL, C. B. GILLEY: The Oxidation of Primary Alcohols to Methyl Esters and Diols to Lactones Using Trichloroisocyanuric Acid. Synth. Commun., 33, 2003 (2003).
7. C. E. McDONALD, L. E. NICE, A. W. SHAW, N. S. NESTOR: Calcium Hypochlorite-mediated Oxidation of Primary Alcohols to Methyl-esters. Tetrahedron Lett, 34, 2741 (1993).
8. C. E. McDONALD, H. L. HOLCOMB, T. W. LEATHERS, K. E. KENNEDY: The Oxidation of Primary Alcohols to Methyl Esters and Lactones Using N-iodosuccinimide. Microchem. J., 47, 115 (1993).
9. T. SHONO, H. MASUDA, H. MURASE, M. SHIMOMURA, S. KASHIMURA: Electroorganic Chemistry. Facile Electroreduction of Methyl-esters and N,N-dimethylamides of Aliphatic Carboxylic Acids to Primary Alcohols. J. Org. Chem., 57, 1061 (1992).
10. J. N. MILOVANOVIC, M. VASOJEVIC, S. GOJKOVIC: Oxidation of Primary Alcohols to Methyl Esters Using tert-butyl Hypochlorite, Pyridine and Methyl Alcohol. J. Chem. Soc. Perkin Trans., 2, 1231 (1991).
11. W. HAIJING, D. QIWEI: Direct Synthesis of Butyl Butyrate from Butanol. Speciality Petrochemicals, 1, 20 (2002).
12. K. INUI, T. KURABAYASHI, S. SATO: Direct Synthesis of Ethyl Acetate from Ethanol Carried out under Pressure. J. Catal., 212, 207 (2002).
13. K. INUI, T. KURABAYASHI, S. SATO: Direct Synthesis of Ethyl Acetate from Ethanol over CuZn-Zr-Al-O Catalyst Appl. Catal. A, 1-2, 237 (2002).
14. K. INUI, T. KURABAYASHI, S. SATO, N. ICHIKAWA: Effective Formation of Ethyl Acetate from Ethanol over Cu-Zn-Zr-Al-O Catalyst J. Mol. Catal. A: Chem., 216, 147 (2004).
15. S. MURAHASHI, T. NAOTA, K. ITO, Y. MAEDA, H. TAKI: Ruthenium-catalyzed Oxidative Transformation of Alcohols and Aldehydes to Esters and Lactones. J. Org. Chem., 52, 4319 (1987).
16. N. A. OWSTON, A. J. PARKER, J. M. J. WILLIAMS: Oxidation of Primary Alcohols to Methyl Esters by Hydrogen Transfer. Chem. Commun., 5, 624 (2008).
17. I. S. NIELSEN, E. TAARNING, K. EGEBLAD, R. MADSEN, C. H. CHRISTENSEN: Direct Aerobic Oxidation of Primary Alcohols to Methyl Esters Catalyzed by a Heterogeneous Gold Catalyst. Catal. Lett., 116, 35 (2007).
18. A. IZUMI, Y. OBORA, S. SAKAGUCHI, Y. ISHII: Oxidative Dimerization of Primary Alcohols to Esters Catalyzed by Iridium Complexes. Tetrahedron Lett., 47, 9199 (2006).
19. T. SUZUKI, T. MATSUO, K. WATANABE, T. KATOH: Iridium-catalyzed Oxidative Dimerization of Primary Alcohols to Esters Using 2-butanone as an Oxidant. Synlett., 9, 1453 (2005).
20. 2 Molecules, 13, 3236 (2008).
21. J. PIERA, J. E. BACKVALL: Catalytic Oxidation of Organic Substrates by Molecular Oxygen and Hydrogen Peroxide by Multistep Electron Transfer - A Biomimetic Approach. Angew. Chem. Int. Ed., 47, 3506 (2008).
22. R. H. LIU, X. M. LIANG, C. Y. DONG, X. Q. HU: Transition-metal-free: A Highly Efficient Catalytic Aerobic Alcohol Oxidation Process. J. Am. Chem. Soc., 126, 4112 (2004).
23. R. H. MU, Z. Q. LIU, Z. J. YANG, Z. G. LIU, L. M. WU, Z. L. LIU: An Efficient Catalytic Aerobic Oxidation of Alcohols in Water Using Hypervalent Iodine(V). Adv. Synth. Catal., 347, 1333 (2005).
24. D. LENOIR: Selective Oxidation of Organic Compounds - Sustainable Catalytic Reactions with Oxygen and without Transition Metals? Angew. Chem. Int. Ed., 45, 3206 (2006).
25. Y. XIE, W. M. MO, D. XU, Z. L. SHEN, N. SUN, B. X. HU: Efficient NO Equivalent for Activation of Molecular Oxygen and Its Applications in Transition-metal-free Catalytic Aerobic Alcohol Oxidation. J. Org. Chem., 72, 4288 (2007).
26. 2 Catalyst: A Transition-metalfree Approach to Efficient Aerobic Oxidation of Alcohols to Aldehydes and Ketones under Mild Conditions. Chem. Eur. J., 14, 2679 (2008).
27. C. DOGO-ISONAGIE, T. BEKELE, S. FRANCE, J. WOLFER, A. WEATHERWAX, A. E. TAGGI: Scalable Methodology for the Catalytic, Asymmetric a-bromination of Acid Chlorides. J. Org. Chem., 71, 8946 (2006).
28. N. C. MARZIANO, L. RONCHIN, C. TORTATO, S. RONCHIN, A. VAVASORI: Selective Oxidations by Nitrosating Agents. Part 2: Oxidations of Alcohols and Ketones over Solid Acid Catalysts. J. Mol. Catal. A: Chem., 235, 26 (2005).
29. L. KRIM, N. LACOME: The NO Dimer, N-14 and N-15 Isotopomers Isolated in Argon Matrix: A Near-, Mid-, and Far-infrared Study. J. Phys. Chem. A, 102, 2289 (1998).
30. G. A. HIEGEL, C. D. BAYNE, Y. DONDE, G. S. TAMASHIRO, L. A. HILBERATH: The Oxidation of Aldehydes to Methyl Esters Using Trichloroisocyanuric Acid. Synth. Commun., 26, 2633 (1996).