4-N,N-dimethylaminopyridine promoted selective oxidation of methyl aromatics with molecular oxygen

Molecules

Volumn 17, Issue 4, 2012, Pages 3957-3968

  Zhang, Zhan ^a,b   Gao, Jin ^a   Wang, Feng ^a   Xu, Jie ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

4 N; Methyl aromatics; Molecular oxygen; N dimethylaminopyridine; Organocatalysis; Selective oxidation

Indexed keywords

4 AMINOPYRIDINE; 4 DIMETHYLAMINOPYRIDINE; 4-DIMETHYLAMINOPYRIDINE; BENZYL BROMIDE; BENZYL DERIVATIVE; DRUG DERIVATIVE; OXYGEN; PYRIDINE; PYRIDINE DERIVATIVE; SOLVENT;

ARTICLE; CATALYSIS; CHEMISTRY; DRUG EFFECT; NUCLEAR MAGNETIC RESONANCE; OXIDATION REDUCTION REACTION; TEMPERATURE;

4-AMINOPYRIDINE; BENZYL COMPOUNDS; CATALYSIS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXIDATION-REDUCTION; OXYGEN; PYRIDINES; SOLVENTS; TEMPERATURE;

EID: 84860253175     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17043957     Document Type: Article

References (33)

1. Sheldon, R.A.; Arends, I.W.C.E. Organocatalytic oxidations mediated by nitroxyl radicals. Adv. Synth. Catal. 2004, 346, 1051-1071.
2. Punniyamurthy, T.; Velusamy, S.; Iqbal, J. Recent advances in transition metal catalyzed oxidation of organic substrates with molecular oxygen. Chem. Rev. 2005, 105, 2329-2363.
3. Suresh, A.K.; Sharma, M.M.; Sridhar, T. Engineering aspects of industrial liquid-phase air oxidation of hydrocarbons. Ind. Eng. Chem. Res. 2000, 39, 3958-3997.
4. Piera, J.; Backvall, J.E. Catalytic oxidation of organic substrates by molecular oxygen and hydrogen peroxide by multistep electron transfer-a biomimetic approach. Angew. Chem. Int. Ed. Engl. 2008, 47, 3506-3523.
5. Matienko, L.I.; Mosolova, L.A.; Zaikov, G.E. Selective catalytic oxidation of hydrocarbons. New prospects. Russ. Chem. Rev. 2009, 78, 211-230.
6. Kesavan, L.; Tiruvalam, R.; Ab Rahim, M.H.; bin Saiman, M.I.; Enache, D.I.; Jenkins, R.L.; Dimitratos, N.; Lopez-Sanchez, J.A.; Taylor, S.H.; Knight, D.W.; et al. Solvent-free oxidation of primary carbon-hydrogen bonds in toluene using Au-Pd alloy nanoparticles. Science 2011, 331, 195-199.
7. Besson, M.; Gallezot, P. Deactivation of metal catalysts in liquid phase organic reactions. Catal. Today 2003, 81, 547-559.
8. Partenheimer, W. Methodology and scope of metal bromide autoxidation of hydrocarbons. Catal. Today 1995, 23, 69-158.
9. Jarup, L. Hazards of heavy metal contamination. Brit. Med. Bull. 2003, 68, 167-182.
10. Fokin, A.A.; Schreiner, P.R. Metal-free, selective alkane functionalizations. Adv. Synth. Catal. 2003, 345, 1035-1052.
11. Ohkubo, K.; Mizushima, K.; Iwata, R.; Souma, K.; Suzuki, N.; Fukuzumi, S. Simultaneous production of p-tolualdehyde and hydrogen peroxide in photocatalytic oxygenation of p-xylene and reduction of oxygen with 9-mesityl-10-methylacridinium ion derivatives. Chem. Commun. 2010, 46, 601-603.
12. Ohkubo, K.; Fukuzumi, S. 100% selective oxygenation of p-xylene to p-tolualdehyde via photoinduced electron transfer. Org. Lett. 2000, 2, 3647-3650.
13. Tada, N.; Hattori, K.; Nobuta, T.; Miura, T.; Itoh, A. Facile aerobic photooxidation of methyl group in the aromatic nucleus in the presence of an organocatalyst under vis irradiation. Green Chem. 2011, 13, 1669-1671.
14. Yang, G.Y.; Ma, Y.F.; Xu, J. Biomimetic catalytic system driven by electron transfer for selective oxygenation of hydrocarbon. J. Am. Chem. Soc. 2004, 126, 10542-10543.
15. Yang, X.M.; Wang, Y.; Zhou, L.P.; Chen, C.; Zhang, W.; Xu, J. Efficient aerobic oxidation of hydrocarbons with O2 catalyzed by DDQ/NHPI. J. Chem. Technol. Biotechnol. 2010, 85, 564-568.
16. Zhang, Q.H.; Chen, C.; Ma, H.; Miao, H.; Zhang, W.; Sun, Z.Q.; Xu, J. Efficient metal-free aerobic oxidation of aromatic hydrocarbons utilizing aryl-tetra halogenated n-hydroxyphthalimides and 1, 4-diamino-2, 3-dichloroanthraquinone. J. Chem. Technol. Biotechnol. 2008, 83, 1364-1369.
17. Einhorn, C.; Einhorn, J.; Marcadal, C.; Pierre, J.L. Oxidation of organic substrates by molecular oxygen mediated by n-hydroxyphthalimide (NHPI) and acetaldehyde. Chem. Commun. 1997, 447-448.
18. Matsunaka, K.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. A remarkable effect of quaternary ammonium bromide for the n-hydroxyphthalimide-catalyzed aerobic oxidation of hydrocarbons. Tetrahedron Lett. 1999, 40, 2165-2168.
19. Melone, L.; Gambarotti, C.; Prosperini, S.; Pastori, N.; Recupero, F.; Punta, C. Hydroperoxidation of tertiary alkylaromatics catalyzed by n-hydroxyphthalimide and aldehydes under mild conditions. Adv. Synth. Catal. 2011, 353, 147-154.
20. Raghavendrachar, P.; Ramachandran, S. Liquid-phase catalytic-oxidation of para-xylene. Ind. Eng. Chem. Res. 1992, 31, 453-462.
21. Hirashima, S.; Nobuta, T.; Tada, N.; Miura, T.; Itoh, A. Direct aerobic photo-oxidative synthesis of aromatic methyl esters from methyl aromatics via dimethyl acetals. Org. Lett. 2010, 12, 3645-3647.
22. Sugai, T.; Itoh, A. Aerobic photo-oxidation in the presence of catalytic allylbromide. Tetrahedron Lett. 2007, 48, 2931-2934.
23. Tong, X.L.; Xu, J.; Miao, H. Highly efficient and metal-free aerobic hydrocarbons oxidation process by an o-phenanthroline-mediated organocatalytic system. Adv. Synth. Catal. 2005, 347, 1953-1957.
24. Tong, X.L.; Xu, J.; Miao, H.; Gao, J. New efficient organocatalytic oxidation of Benzylic Compounds by Molecular Oxygen under Mild Conditions. Tetrahedron Lett. 2006, 47, 1763-1766.
25. Tong, X.L.; Xu, J.; Miao, H.; Gao, J.; Sun, Z.Q.; Zhang, W. Highly efficient and organic nitrogen-containing cation-promoted aerobic oxidation of alkylaromatics in the presence of N-hydroxyphthalimide. J. Chem. Technol. Biotechnol. 2009, 84, 1762-1766.
26. Dugmore, G.M.; Powels, G.J.; Zeelie, B. Mechanistic aspects of benzylic bromide formation and oxidation during the cobalt acetate bromide catalyzed oxidation of alkylbenzenes in carboxylic-acids. J. Mol. Catal. A Chem. 1995, 99, 1-12.
27. Metelski, P.D.; Adamian, V.A.; Espenson, J.H. Mechanistic role of benzylic bromides in the catalytic autoxidation of methylarenes. Inorg. Chem. 2000, 39, 2434-2439.
28. Prades, A.; Corberan, R.; Poyatos, M.; Peris, E. A simple catalyst for the efficient benzylation of arenes by using alcohols, ethers, styrenes, aldehydes, or ketones. Chem.-Eur. J. 2009, 15, 4610-4613.
29. Kaneko, M.; Hayashi, R.; Cook, G.R. Intermolecular friedel-crafts reaction catalyzed by InCl3. Tetrahedron Lett. 2007, 48, 7085-7087.
30. Partenheimer, W. Chemistry of the oxidation of acetic acid during the homogeneous metal-catalyzed aerobic oxidation of alkylaromatic compounds. Appl. Catal. A Gen. 2011, 409, 48-54.
31. Csanyi, L.J.; Jaky, K. Characteristics of cationic phase-transfer catalysts in the oxidation of hydrocarbons by O2. Phys. Chem. Chem. Phys. 2001, 3, 2018-2024.
32. Csanyi, L.J.; Jaky, K.; Palinko, I.; Rockenbauer, A.; Korecz, L. The role of onium salts in the oxidation of hydrocarbons by O2 catalysed by cationic phase-transfer reagents. Phys. Chem. Chem. Phys. 2000, 2, 3801-3805.
33. Plooster, M.N.; Garvin, D. The hydrogen-bromine reaction at elevated temperatures. J. Am. Chem. Soc. 1956, 78, 6003-6008.