Bis(trimethylsilyl)chromate catalyzed oxidations of alcohols to aldehydes and ketones with periodic acid

Molecules

Volumn 12, Issue 5, 2007, Pages 958-964

  Asadolah, Karim ^a   Heravi, Majid M ^a   Hekmatshoar, Rahim ^a   Majedi, Soma ^a  

^a ALZAHRA UNIVERSITY   (Iran)

Author keywords

BTSC; Carbonyl compounds; Oxidation; Periodic acid

Indexed keywords

ALDEHYDE; BIS(TRIMETHYLSILYL)CHROMATE; KETONE; ORGANOMETALLIC COMPOUND; PERIODIC ACID; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION;

ALDEHYDES; CATALYSIS; KETONES; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PERIODIC ACID; TRIMETHYLSILYL COMPOUNDS;

EID: 34249903385     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/12050958     Document Type: Article

References (34)

1. Hudlicky, M.; Oxidation in Organic Chemistry; American Chemical Society: Washington, DC 1990.
2. Varma, R. S.; Saini, R. K. Wet alumina supported chromium (VI) oxide: Selective oxidation of alcohols in solventless system. Tetrahedron Lett. 1998, 39, 1481-1482.
3. (a) Velusamy, S.; Srenvasan, A.; Punniyamurthy, T. Copper (II) catalyzed selective oxidation of primary alcohols to aldehydes with atmospheric oxygen. Tetrahedron Lett. 2006, 47, 923-926;
4. (b) Herrerias, C. I.; Zhang, T. Y.; Li, Ch. Catalytic oxidations of alcohols to carbonyl compounds by oxygen under solvent-free and transition-metal-free conditions. Tetrahedron Lett. 2006, 47, 13-17;
5. (c) Mardani, H. R.; Golchobian, H. Effective oxidation of benzylic and aliphatic alcohols with hydrogen peroxide catalyzed by a manganese(III) Schiff-base complex under solvent-free conditions. Tetrahedron Lett. 2006, 47, 2349-2352;
6. 2 atmosphere. Tetrahedron Lett. 2005, 46, 8483-8486;
7. (e) Hunsen, M. Pyridinium chlorochromate catalyzed oxidation of alcohols to aldehydes and ketones with periodic acid. Tetrahedron Lett. 2005, 46, 1651-1653.
8. 110]: A heteropoly acid catalyzed acetylation of alcohols and phenols in acetic anhydride. J. Mol Catal. A. Chem. 2006, 253, 16-19;
9. (b) Heravi, M. M.; Bakhtiari, Kh.; Bamoharram, F. F. An efficient and chemoselective synthesis of acylals from aromatic aldehydes and their regeneration, catalyzed by 12-molybdo-phosphoric acid. Catal. Commun. 2006, 7, 499-501;
10. (c) Heravi, M. M.; Bakhtiari, Kh.; Bamoharram, F. F. 12-Molybdophosphoric acid: A recyclable catalyst for the synthesis of Biginelli-type 3,4-dihydropyrimidine-2(1H)-ones. Catal. Commun. 2006, 7, 373-376;
11. (14-), as a green and reusable catalyst. J. Mol. Catal. A. Chem. 2006, 252, 90-95;
12. 40. J. Mol. Catal. A. 2006, 249, 1-3;
13. (14-): A green, efficient and reusable catalyst for esterification of salicylic acid with aliphatic and benzylic alcohols. Applied Cat. A. 2006,302,42-47;
14. 110] as an efficient catalyst for the one-pot synthesis of alpha-amino nitriles. Synlett, 2006, 11, 1768-1770;
15. (h) Heravi, M. M.; Derikvand, F.; Haghigi, M. "On water": Rapid Knoevenagel condensation using sodium pyruvate. Lett. Org. Chem. 2006, 3, 297-299;
16. (i) Heravi, M. M.; Derikvand, F.; Oskooie, H. A.; Hekmatshoar, R. Zeofen: a user friendly agent for oxidation of the Hantzsch 1,4-dihydro-pyridines. J. Chem. Res. 2006, 3, 168-169;
17. (j) Fotouhi, L.; Nematolahi, D.; Heravi, M. M.; Tamari, E. An efficient electrochemical method for a unique synthesis of new derivatives of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one. Tetrahedron Lett, 2006, 47, 1713-1716.
18. (a) Heravi, M. M.; Derikvand, F.; Ghassemzadeh, M. Tetrameric DABCO-bromine complex: A novel reagent for regeneration of carbonyl compounds from aldoximes and ketoximes. Synth Commun. 2006, 36,581-585;
19. (b) Heravi, M. M.; Derikvand, F.; Ghassemzadeh, M.; Neumuller, B. Synthesis, characterization and structure of a tetrameric DABCO-bromine complex: a novel oxidizing agent for oxidation of alcohols to carbonyl compounds. Tetrahedron Lett. 2005, 46, 6243-6245;
20. (c) Heravi, M. M.; Mirza Aghajan, Z. Microwave-assisted oxidation of alcohols using wet alumina supported ammonium chlorochromate in solventless system. Naturforsch. 1999, 54, 815-817;
21. (d) Heravi, M. M.; Ajami, D.; Tabar hydra, K.; Ghassemzadeh, M. Remarkable fast microwave-assisted zeolite HZSM-5 catalyzed oxidation of alcohols with chromium trioxide under solvent-free conditions. J. Chem. Res. 1999, 5, 334-335;
22. (e) Heravi, M. M. Ajami, D.; Aghapoor, K.; Ghassemzadeh, M. 'Zeofen', a user-friendly oxidizing reagent Chem. Commun. 1999, 89, 833-834;
23. (f) Heravi, M. M.; Ajami, D.; Ghassemzadeh, M. Wet alumina supported chromium (VI) oxide: A mild, efficient and inexpensive reagent for oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers in a solventless system. Synthesis, 1999, 3, 393-394.
24. (a) Heravi, M. M.; Derikvand, F.; Oskooei, H. A.; Hekmatshoar, R. Silica gel-supported bis(trimethylsilyl) chromate: Oxidation of 1,4-dihydropyridines to pyridines. Synth. Commun. 2006, 36, 77-82;
25. (b) Heravi, M. M.; Ajami, D. Oxidative deprotection of tetrahydropyranyl ethers to carbonyl compounds with montmorillonite K-10 supported bis(trimethylsilyl) chromate under non-aqueou conditions. J. Chem. Res. 1998, 718-719;
26. (c) Heravi, M. M.; Ajami, D.; Tabar-Heydar, K.; Mojtahedi, M. M. Direct oxidative deprotection using montmorillonite supported bis-(trimethylsilyl) chromate. J. Chem. Res. 1998, 9, 620-621;
27. (d) Heravi, M. M.; Ajami, D.; Tajbakhsh, M.; Ghassemzadeh, M. Clay supported bis-(trimethylsilyl)-chromate: An efficient reagent for oxidative deoximation. Monatsh. Chem. 2000, 131, 1109-1113;
28. (e) Heravi, M. M.; Ajami, D. Clay supported bis(trimethylsilyl)chromate: Oxidative deprotection of tetrahydropyranyl ethers under solvent-free conditions using microwaves. Monatsch. Chem. 1999, 130, 709-712;
29. (f) Khaleghi, Sh.; Heravi, M. M.; Derikvand, F. Bis(trimethylsilyl) chromate: An efficient reagent for cleavage of phenylhydrazones. Phosphorus Sulfur Silicon 2006, 181, 227-231.
30. Zhao, M.; Li, J.; Song, Z.; Desmond, R.; Taschaen, D. M.; Grabowski, E. J. J.; Reider, P. A novel chromium trioxide catalyzed oxidation of primary alcohols to the carboxylic acids. Tetrahedron Lett. 1998, 39, 5323-5326.
31. (a) Heravi, M. M.; Beheshtiha,Y. S.; Ghasemzadeh, M.; Hekmat Shoar, R.; Sarmadi, N. Solid state deoximation with clay supported ammonium chlorochromate: Regeneration of carbonyl compounds using microwaves in a solventless system. Monatsh. Chem. 2000, 31, 187-190;
32. (b) Heravi M. M.; Rajabzadeh, G.; Bamoharram, F. F.; Seifi, N. An eco-friendly catalytic route for synthesis of 4-amino-pyrazolo[3,4-d]pyrimidine derivatives by Keggin heteropolyacids under classical heating and microwave irradiation. J. Mol. Catal. A: Chem. 2006, 256, 238-241.
33. 3. Synthesis 2002, 17, 2484-2486.
34. Kim, S. S.; Nehru, K. A Mild and Efficient Oxidation of Alcohols to Carbonyl Compounds by Periodic Acid Catalyzed by 2,2,6,6-Tetramethylpiperidinyl- 1-oxyl. Synlett 2002, 4, 616-617.