2,6-Dicarboxypyridinium fluorochromate-promoted oxidation of alkyl-arenes into carbonyl compounds under nonaqueous and aprotic conditions

Synthetic Communications

Volumn 42, Issue 5, 2012, Pages 678-685

  Sarrafi, Yaghoub ^a   Tajbakhsh, Mahmood ^a   Hosseinzadeh, Rahman ^a   Sadatshahabi, Marzieh ^a   Alimohammadi, Kamal ^a  

^a UNIVERSITY OF MAZANDARAN   (Iran)

Author keywords

2,6 dicarboxypyridinium fluorochromate; Alkyl arenes; Carbonyl compounds; Oxidation

Indexed keywords

CARBONYL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDINIUM DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; OXIDATION;

EID: 80755188177     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.529228     Document Type: Article

References (30)

1. Warren, S. Organic Synthesis: The Disconnection Approach; John Wiley and Sons: Singapore, 2004; p. 57, 201, and 330
2. Ghosh, S.; Banik, B. K.; Ghatak, U. R. An expeditious synthesis of 1,2,3,4-tetrahydro-1,1-dimethylphenanthrenes. J. Chem. Soc., Perkin Trans. 1. 1991, 3195-3197.
3. Compere, D.; Marazano, C.; Das, B. C. An enantioselective access to lobelia alkaloids. J. Org. Chem. 1999, 64, 4528-4532.
4. Larock, R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations; VCH: New York, 1989; p. 591
5. Khan, A. T.; Parvin, T.; Choudhury, L. H.; Ghosh, S. A simple synthetic protocol for oxidation of alkyl arenes into ketones using a combination of HBr-H2O2. Tetrahedron Lett. 2007, 48, 2271-2274
6. Yamazaki, S. Chromium(VI) oxide-catalyzed benzylic oxidation with periodic acid. Org. Lett. 1999, 1, 2129-2132
7. Choudary, B. M.; Prasad, A. D.; Bhuma, V.; Swapna, V. Chromium-pillared clay as a catalyst for benzylic oxidation and oxidative deprotection of benzyl ethers and benzylamines: A simple and convenient procedure. J. Org. Chem. 1992, 57, 5841-5844
8. Chidambaram, N.; Chandrasekaran, S. tert-Butyl hydroperoxide-pyridinium dichromate: A convenient reagent system for allylic and benzylic oxidations. J. Org. Chem. 1987, 52, 5048-5051.
9. Hosseinzadeh, R.; Tajbakhsh, M.; Vahedi, H. Selective oxidation of methylarenes with pyridinium chlorochromate. Synlett 2005, 2769-2770. (Pubitemid 41654290)
10. Kim, S. S.; Sar, S.; Tamrakar, P. Gif chemistry for oxidation of activated methylenes to ketones. Bull. Korean Chem. Soc. 2002, 23, 937-938.
11. Murahashi, S. I.; Komiya, N.; Oda, Y.; Kuwabara, T.; Naota, T. Ruthenium-catalyzed oxidation of alkanes with tert-butyl hydroperoxide and peracetic acid. J. Org. Chem. 2000, 65, 9186-9193. (Pubitemid 32015179)
12. Catino, A. J.; Nichols, J. M.; Choi, H.; Gottipamula, S.; Doyle, M. P. Benzylic oxidation catalyzed by dirhodium(II, III) caprolactamate. Org. Lett. 2005, 23, 5167-5170. (Pubitemid 41713228)
13. Mohapatra, S. K.; Selvam, P. A highly selective, heterogeneous route to enones from allylic and benzylic compounds over mesoporous CrMCM-41 molecular sieves. J. Catal. 2007, 249, 394-396. (Pubitemid 47016495)
14. Badri, R.; Soleymani, M. 3,6-Bis(triphenylphosphonium) cyclohexene peroxodisulfate as an efficient and mild oxidizing agent for conversion of alkylbenzenes to corresponding carbonyl compounds. Synth. Commun. 2002, 32, 2385-2389. (Pubitemid 34848026)
15. Bonvin, Y.; Callens, E.; Larrosa, I.; Henderson, D. A.; Oldham, J.; Burton, A. J.; Barrett, A. G. M. Bismuth-catalyzed benzylic oxidations with tert-butyl hydroperoxide. Org. Lett. 2005, 21, 4549-4552. (Pubitemid 41507039)
16. Patel, S.; Mishra, B. K. Chromium(VI) oxidants having quaternary ammonium ions: Studies on synthetic applications and oxidation kinetics. Tetrahedron 2007, 63, 4367-4406 (Pubitemid 46604749)
17. Tajbakhsh, M.; Mohammadpoor-Baltork, I.; Alimohammadi, K. An efficient and selective solid state oxidation of thiols to disulfides with quinolinium fluorochromate on silica gel. Monatsh Chem. 2003, 134, 1571-1575 (Pubitemid 38005157)
18. Tajbakhsh, M.; Alimohammadi, K.; Ramzanian Lehmali, F.; Barghamadi, M.; Shakeri, A. Quinolinium fluorochromate: An efficient and convenient reagent for oxidative cleavage of thioacetals to their parent carbonyl compounds. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 2587-2591. (Pubitemid 43175218)
19. Tajbakhsh, M.; Hosseinzadeh, R.; Yazdani-Niaki, 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
20. Tajbakhsh, M.; Hosseinzadeh, R.; Yazdani-Niaki, M. 2,6- Dicarboxypyridinium chlorochromate: A mild, efficient, and selective reagent for oxidative deprotection of oximes to carbonyl compounds. Tetrahedron Lett. 2002, 43, 9413-9415
21. Tajbakhsh, M.; Hosseinzadeh, R.; Ramzanian Lehmali, F.; Sadatshahabi, M. 2,6-Dicarboxyopyridinium fluorochromate: A mild and efficient reagent for oxidative deprotection of oximes, phenylhydrazones to their corresponding carbonyl compounds under solvent-free conditions. J. Chin. Chem. Soc. 2005, 52, 1005-1009. (Pubitemid 41703209)
22. Hosseinzadeh, R.; Tajbakhsh, M.; Shakoori, A. R.; Yazdani-Niaki, M. 2,6-Dicarboxypyridinium chlorochromate: An efficient and selective reagent for the mild deprotection of acetals, thioacetals, and 1,1-diacetates to carbonyl compounds. Monatsh Chem. 2004, 135, 1243-1249. (Pubitemid 39422130)
23. Tajbakhsh, M.; Hosseinzadeh, R.; Shakoori, A. R. 2,6-Dicarboxypyridinium chlorochromate: An efficient and selective reagent for the oxidation of thiols to disulfides and sulfides to sulfoxides. Tetrahedron Lett. 2004, 45,1889-1893 (Pubitemid 38220800)
24. Tajbakhsh, M.; Mohammadpoor Baltork, I.; Ramzanian Lehmali, F. Quinulinium fluorochromate C9H7NHCrO3F: An efficient and convenient reagent for the oxidative deprotection of trimethylsilyl ethers in nonaqueous conditions. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 2617-2620 (Pubitemid 38142590)
25. Tajbakhsh, M.; Khazaei, A.; Shabani Mahalli, M.; Ghorbani Vaghi, R. N,N-Dibromobenzenesulfonamide as a reagent for oxidative cleavage of oximes to their parent carbonyl compounds under non-aqueous and aprotic conditions. J. Chem. Res., Synop. 2004, 141-142
26. Tajbakhsh, M.; Lakouraj, M. M.; Fadavi, A. Allyltriphenylphosphonium peroxodisulfate (CH2=CHCH2PPh3)2S2O8: An efficient and convenient reagent for the oxidation of alcohols, silyl, and THP ethers under nonaqueous conditions. Synth. Commun. 2004, 34, 1173-1181. (Pubitemid 38452244)
27. Tajbakhsh, M.; Hosseinzadeh, R.; Sadatshahabi, M. 2,6-Dicarboxypyridinium fluorochromate: A mild and efficient reagent for oxidative deprotection of trimethylsilyl ethers to their corresponding carbonyl compounds. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 2279-2283. (Pubitemid 41491343)
28. Tajbakhsh, M.; Hosseinzadeh, R.; Sadatshahabi, M. Synthesis and application of 2,6-dicarboxypyridinium fluorochromate as a new solid phase oxidant. Synth. Commun. 2005, 35, 1547-1554. (Pubitemid 40867317)
29. Furniss, B. S.; Manaford, A. J.; Rogers, V.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 4th Ed.; 1978; p. 1192, 1196
30. Shriner, R. L.; Hermann, C. K. F.; Morrill, T. C.; Curtin, D. Y.; Fuson, R. C. The Systematic Identification of Organic Compounds; Wiley: New York, 2004; p. 652.