N-bromosuccinimide: A facile reagent for the oxidation of benzylic alcohols to aldehydes

Synthetic Communications

Volumn 37, Issue 9, 2007, Pages 1571-1577

  Adimurthy, Subbarayappa ^a   Patoliya, Paresh U ^a  

^a Central Salt and Marine Chemicals Research Institute CSIR   (India)

Author keywords

Aldehydes; Benzylic alcohols; N bromosuccinimide

Indexed keywords

ALDEHYDE; BENZYL ALCOHOL; N BROMOSUCCINIMIDE;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENVIRONMENTAL TEMPERATURE; OXIDATION; STRUCTURE ACTIVITY RELATION;

EID: 34248573444     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701239023     Document Type: Article

References (40)

1. (a) Larock, R. C. Comprensive Organic Transformations; Wiley: New York, 1999;
2. (b) Brink, G. J. T.; Andrews, I. W. C. E.; Sheldon, R. A. Green, catalytic oxidation of alcohols in water. Science 2000, 287, 1636-1639;
3. (c) Barrett, A. G. M.; Braddock, D. C.; McKinnell, R. M.; Waller, F. J. Ytterbium(III) triflate as a recyclable catalyst for the selective atom economic oxidation of benzyl alcohols to benzaldehydes. Synlett 1999, 1489-1490;
4. (d) Sato, K.; Takagi, J.; Aoki, M.; Noyori, R. Hydrogen peroxide oxidation of benzylic alcohols to benzaldehydes and benzoic acids under halide-free conditions. Tetrahedron Lett. 1998, 39, 7549-7552;
5. (e) Barhate, N. B.; Sasidharan, M.; Sudalai, A.; Wakharkar, R. D. Selective catalytic oxidation of benzylic alcohols to the corresponding carbonyl compounds with TBHP over CrS-2. Tetrahedron Lett. 1996, 37, 2067-2070.
6. Singh, R. P.; Subbarao, H. N.; Suk, D. Organic reactions in a solid matrix - V: Silica-gel supported chromic acid reagents. Tetrahedron 1979, 35, 1789-1793.
7. Ley, S. V.; Madin, A.; Trost, B. M.; Flemming, I. Comprensive Organic Synthesis; Pergamon Press: Oxford, 1991, Vol. 7, pp. 305-327.
8. Collons, J. C.; Hess, W. W.; Franck, F. J. Dipyridine-chromium(VI) oxide oxidation of alcohols in dichloromethane. Tetrahedron Lett. 1968, 9, 3363-3366.
9. Corey, E. J.; Fleet, G. W. J. Chromium trioxide-3,5-dimethylpyrazole complex as a reagent for oxidation of alcohols to carbonyl compounds. Tetrahedron Lett. 1973, 14, 4499-4501.
10. Corey, E. J.; Suggs, J. W. Pyridinium chlorochromate: An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds. Tetrahedron Lett. 1975, 16, 2647-4650.
11. Corey, E. J.; Schmith, G. Useful procedures for the oxidation of alcohols involving pyridinium dichromate in approtic media. Tetrahedron Lett. 1979, 20, 399-402.
12. Guziec, F. S.; Luzzio, F. A. The oxidation of alcohols using 2,2′-bipyridinium chlorochromate. Synthesis 1980, 691-693.
13. 3F (PFC), oxidations: Stoichiometry of oxidation of alcohols, evidence for oxygen transfer, and the identity of the reduced chromium species. Tetrahedron 1987, 43, 5389-5392.
14. Murugasan, V.; Pandurangan, A. Quinolinium fluorochromate - A new reagent for the oxidation of organic compounds. Indian J. Chem. Sec. B 1992, 31B, 377-378.
15. Srinivasan, R.; Ramesh, C. V.; Madhulatha, W.; Balasubramanian, K. Oxidation of alcohols by quinolinium chlorochromate. Indian J. Chem. Sec. B 1996, 35B, 480-481.
16. Tajbakhsh, M.; Hosseinzadeh, R.; Niaki, Y. M. Synthesis and application of 2,6-dicarboxypyridinium chlorochromate as a new oxidizing reagent for alcohols, silyl ethers, and THP ethers under mild and non-aqueous conditions. J. Chem. Res. Synop. 2002, 508-510.
17. Schultz, H. S.; Freyermuth, H. B.; Buc, S. R. New catalysts for the oxidation of sulfides to sulfones with hydrogen peroxide. J. Org. Chem. 1963, 28, 1140-1142.
18. 3- (M = Mo or W). Chem. Lett. 1994, 23, 1-4.
19. Gresley, N. M.; Griffith, W. P.; Laemmel, A. C.; Nogueira, H. I. S.; Parkin, B. C. Studies on polyoxo- and polyperoxo-metalates part 5: Peroxide-catalysed oxidations with heteropolyperoxo-tungstates and -molybdates. J. Mol. Catal. A: Chem. 1997, 117, 185-198.
20. Sato, K.; Hyodo, M.; Aoki, M.; Zheng, X. Q.; Noyori, R. Oxidation of sulfides to sulfoxides and sulfones with 30% hydrogen peroxide under organic solvent- and halogen-free conditions. Tetrahedron 2001, 57, 2469-2476.
21. (a) Kaneda, K.; Fuji, M.; Morioka, K. Highly selective oxidation of allylic alcohols to α,β-unsaturated aldehydes using Pd cluster catalysts in the presence of molecular oxygen. J. Org. Chem. 1996, 61, 4502-4505;
22. (b) Peterson, K. P.; Larock, R. C. Palladium-catalyzed oxidation of primary and secondary allylic and benzylic alcohols. J. Org. Chem. 1998, 63, 3185-3189;
23. (c) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. Heterogeneous oxidation of allylic and benzylic alcohols catalyzed by Ru-Al-Mg hydrotalcites in the presence of molecular oxygen. J. Org. Chem. 1998, 63, 1750-1751;
24. (e) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Creation of a monomeric Ru species on the surface of hydroxyapatite as an efficient heterogeneous catalyst for aerobic alcohol oxidation. J. Am. Chem. Soc. 2000, 122, 7144-7145;
25. (f) Chaudhuri, P.; Hess, M.; Muller, J.; Hildenbrand, K.; Bill, E.; Weyhermller, T. K. Aerobic oxidation of primary alcohols (including methanol) by copper(II)- and zinc(II)-phenoxyl radical catalysts. J. Am. Chem. Soc. 1999, 121, 9599-9600;
26. (g) Pagliaro, M.; Ciriminna, R. New recyclable catalysts for aerobic alcohols oxidation: Sol-gel ormosils doped with TPAP. Tetrahedron Lett. 2001, 42, 4511-4514;
27. (h) Sharma, V. B.; Jain, S. L.; Sain, B. Cobalt phthalocyanine catalyzed aerobic oxidation of secondary alcohols: An efficient and simple synthesis of ketones. Tetrahedron Lett. 2003, 44, 383-386.
28. Narasimha Moorthy, J.; Singhal, N.; Ventakrishnan, P. Studies on oxidations with IBX: Oxidation of alcohols to aldehydes under solvent-free conditions. Tetrahedron Lett. 2004, 45, 5419-5424.
29. Lee, J. C.; Lee, J. Y.; Lee, S. J. Efficient oxidation of benzylic alcohols with [hydroxy(tosyloxy)iodo]benzene under microwave irradiation. Tetrahedron Lett. 2004, 45, 4939-4941.
30. Reddy, S. R.; Das, S.; Punniyamurthy, T. Polyaniline supported vanadium catalyzed aerobic oxidation of alcohols to aldehydes and ketones. Tetrahedron Lett. 2004, 45, 3561-3564.
31. Maiti, S. K.; Abdul Malik, K. M.; Bhattacharyya, R. Oxoperxo-molybdenum and -tungsten(VI) complexes: Their synthesis structure and catalytic uses in the peroxidic oxidation of alcohols to aldehydes and ketones. Inorg. Chem. Commun. 2004, 7, 823-828.
32. Kassaee, M. Z.; Sayyed-alangi, S. Z.; Sajjadi-Ghottbabadi, H. Synthesis and reactions of N-methylbenzylammonium flurochromate(VI) on silica gel, a selective and efficient heterogeneous oxidant. Molecules 2004, 9, 825-829.
33. Mallat, T.; Baiker, A. Oxidation of alcohols with molecular oxygen on solid catalysts. Chem. Rev. 2004, 104, 3037-3058, and references therein.
34. Chhikara, B. S.; Chandra, R.; Tandon, V. Oxidation of alcohols with hydrogen peroxide catalyzed by a new imidazolium ion based phosphotungstate in ionic liquid. J. Catal. 2005, 230, 436-439.
35. Rajabi, F.; Karimi, B. Efficient aerobic oxidation of benzylic alcohols using a novel combination N-hydroxy phthalimide (NHPI) and a recyclable heterogeneous cobalt complex. J. Mol. Catal. A: Chem. 2005, 46, 95-99.
36. 6 system. Tetrahedron Lett. 2005, 46, 3323-3326.
37. Egami, H.; Shimizu, H.; Katsuki, T. Aerobic oxidation of primary alcohols in the presence of activated secondary alcohols. Tetrahedron Lett. 2005, 46, 783-786.
38. (a) Ramachandraiah, G.; Ghosh, P. K.; Mehta, A. S.; Adimurthy, S.; Jethva, A. D.; Vaghela, S. S. U.S. Patent No. 6,740,253, May 25, 2004;
39. (b) Ramachandraiah, G.; Ghosh, P. K.; Adimurthy, S.; Bedekar, A. V.; Shukla, D. B. U.S. Patent Appl. No. 10/449723 May 30, 2003; PCT Publication No. WO 2004/106227, December 9, 2004; Indian Patent No. 194811, May 30, 2003.
40. Adimurthy, S.; Ramachandraiah, G.; Bedekar, A. V.; Ghosh, S.; Ranu, B. C.; Ghosh, P. K. Eco-friendly and versatile brominating reagent prepared from liquid bromine precursor. Green Chem. 2006, 8, 916-922; 10.1039/b606586d.