Quinaldinium Chlorochromate(VI), (QnCC) Catalyzed Oxidation of Alcohols with Periodic Acid Under Solvent-Free Conditions and Microwave Irradition

Year 2018, , 679 - 690, 01.01.2018

Melek Canbulat Özdemir

https://doi.org/10.18596/jotcsa.357452

Cited By: 2

Abstract

The economic synthesis of quinaldinium
chlorochromate(VI), C₁₀H₉NH[CrO₃Cl], (QnCC)
was performed by using a 1:1:1 stoichiometric amounts of CrO₃, HCl
(aq) and quinaldine. QnCC was isolated in 99% yield as an orange crystalline
solid and characterized with FT-IR, ¹H-NMR, and ¹³C-NMR. An
efficient, selective, and environmentally friendly oxidation of alcohols with
1.1 equiv. periodic acid (H₅IO₆) catalyzed by QnCC (2 mol%)
is described. The primary and secondary alcohols were oxidized to their
corresponding aldehydes and ketones under solvent-free conditions at room
temperature and MW irradiation in high to excellent yields.

Keywords

alcohols, quinaldinium chlorochromate, periodic acid, solvent-free, microwave irradiation

References

• 1. Larock RC. Comprehensive organic transformations: A guide to functional group preparations. Wiley-VCH; 1999.
• 2. Li G, Enache DI, Edwards J, Carley AF, Knight DW, Hutchings GJ. Solvent-free oxidation of benzyl alcohol with oxygen using zeolite-supported Au and Au – Pd catalysts. Catal Letters. 2006;110(1–2):7–13.
• 3. Ren P, Fu X, Zhang Y. Carbon quantum dots-TiO2 nanocomposites with enhanced catalytic activities for selective liquid phase oxidation of alcohols. Catal Letters. 2017;147(7):1679–85.
• 4. Fardjahromi M, Moghadam M, Tangestaninejad S, Mirkhani V, Mohammadpoor-Baltork I. Manganese ( III ) salophen supported on nanosilica triazine dendrimer as a selective heterogeneous catalyst for oxidation of alcohols with sodium periodate. J Iran Chem Soc. 2017;14(6):1317–23.
• 5. Corey EJ, Suggs JW. Pyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds. Tetrahedron Lett. 1975;16(31):2647–50.
• 6. Bhattacharjee MN, Chaudhuri MK, Dasgupta HS, Roy N, Khathing DT. Pyridinium fluorochromate; A new and efficient oxidant for organic substrates. Synthesis (Stuttg). 1982;1982(7):588–90.
• 7. Corey EJ, Schmidt G. Useful procedures for the oxidation of alcohols involving pyridinium dichromate in aprotic media. Tetrahedron Lett. 1979;20(5):399–402.
• 8. Şendil K, Özgün B. Dipyrazinium tri(fluorotrioxochromate ): An efficient oxidant for organic substrates. Monatshefte für Chemie. 2006;137(12):1529–33.
• 9. Hajipour AR, Bagheri HR, Ruoho AE. Oxidation of alcohols with 1-decyl-4-aza-1-azonia-bicyclo[2.2.2]-octane chlorochromate under conventional and solvent-free conditions. Russ J Org Chem. 2006;42(6):844–8.
• 10. Bora U, Chaudhuri MK, Dey D, Kalita D, Kharmawphlang W, Mandal GC. 3,5-Dimethylpyrazolium fluorochromate(VI), C5H8N2H[CrO3F], (DmpzHFC): A convenient new reagent for oxidation of organic substrates. Tetrahedron. 2001;57(12):2445–8.
• 11. Mansoor SS, Shafi SS. Oxidation of aliphatic alcohols by triethylammonium chlorochromate in non-aqueous medium - A kinetic and mechanistic study. Arab J Chem. 2014;7(3):312–8.
• 12. Bai C, Li A, Yao X, Liu H, Li Y. Efficient and selective aerobic oxidation of alcohols catalysed by MOF-derived Co catalysts. Green Chem. 2016;18(4):1061–9.
• 13. Aryanejad S, Bagherzade G, Farrokhi A. A nanoscale Cu-metal organic framework with Schiff base ligand : Synthesis , characterization and investigation catalytic activity in the oxidation of alcohols. Inorg Chem Commun. 2017;81:37–42.
• 14. Hatefi-Ardakani M, Saeednia S, Pakdin-Parizi Z, Rafeezadeh M. Efficient and selective oxidation of alcohols with tert - BuOOH catalyzed by a dioxomolybdenum ( VI ) Schiff base complex under organic solvent-free conditions. Res Chem Intermed. 2016;42(10):7223–30.
• 15. Hajian R, Alghour Z. Selective oxidation of alcohols with H2O2 catalyzed by zinc polyoxometalate immobilized on multi-wall carbon nanotubes modified with ionic liquid. Chinese Chem Lett. 2017;28(5):971–5.
• 16. Dijksman A, Marino-Gonzalez A, Payeras AM, Arends IWCE, Sheldon RA. Efficient and Selective Aerobic Oxidation of Alcohols into Aldehydes and Ketones Using Ruthenium / TEMPO as the Catalytic System. J Am Chem Soc. 2001;123(28):6826–33.
• 17. Elhamifar D, Yari O, Karimi B. Highly ordered mesoporous organosilica–titania with ionic liquid framework as very efficient nanocatalyst for green oxidation of alcohols. J Colloid Interface Sci. 2017;500:212–9.
• 18. Matsumoto T, Ueno M, Wang N, Kobayashi S. Recent advances in immobilized metal catalysts for environmentally benign oxidation of alcohols. Chem an Asian J. 2008;3(2):196–214.
• 19. Zhao M, Li J, Song Z, Desmond R, Tschaen DM, Grabowski EJJ, et al. A novel chromium trioxide catalyzed oxidation of primary alcohols to the carboxylic acids. Tetrahedron Lett. 1998;39(30):5323–6.
• 20. Hunsen M. Pyridinium chlorochromate catalyzed oxidation of alcohols to aldehydes and ketones with periodic acid. Tetrahedron Lett. 2005;46(10):1651–3.
• 21. Hunsen M. Carboxylic acids from primary alcohols and aldehydes by a pyridinium chlorochromate catalyzed oxidation. Synthesis (Stuttg). 2005;15:2487–90.
• 22. Hunsen M. Fluorochromate-catalyzed periodic acid oxidation of alcohols and aldehydes. J Fluor Chem. 2005;126(9–10):1356–60.
• 23. Martins NMR, Martins LMDRS, Amorim CO, Amaral VS, Pombeiro AJL. Solvent-free microwave-induced oxidation of alcohols catalyzed by ferrite magnetic nanoparticles. Catalyst. 2017;7(7):1–18.
• 24. Şendil K, Özgün H, Üstün E. Two new 1,1,3,3-tetramethylguanidinium halochromates (C5H14N3CrO3X)(X: Cl, F): efficient reagents for oxidation of organic substrates under solvent-free conditions and microwave irradiation. J Chem. 2016;2016:1–8.
• 25. Ghorbani-Vaghei R, Veisi H, Amiri M. Microwave-assisted oxidation of alcohols with N,N,N,N-Tetrabromobenzene-1,3-disulfonamide and poly(N-bromobenzene-1,3-disulfonamide) under solvent-free conditions. J Chinese Chem. 2007;54(5):1257–60.
• 26. Özdemir MC, Özgun HB. Economic synthesis of quinaldinium fluorochromate(VI), (QnFC), and solvent-free periodic acid oxidation of alcohols catalyzed by QnFC. Turkish J Chem. 2014;38(1):63–9.
• 27. Stammreich H, Sala O, Kawai K. Vibrational spectrum and force constants of the monochlorochromate ion. Spectrochim Acta. 1961;17(2):226–32.
• 28. Değirmenbaşı N, Özgün B. Quinaldinium chlorochromate supported on alumina : A new and efficient reagent for the oxidation of alcohols. Monatshefte für Chemie. 2003;134(12):1565–9.
• 29. Furniss BS, Hannaford AJ, Smith PWG, Tatchell AR. Vogel’s textbook of practical organic chemistry. John Wiley & Sons, Inc.; 1989.
• 30. Okumura A, Kitani M, Murata M. Kinetic studies of the catalytic oxygen exchange of chromate ions with water by periodate ions. Bull Chem Soc Jpn. 1994;67(6):1522–30.
• 31. Xu L, Trudell ML. A mild and efficient oxidation of alcohols to aldehydes and ketones with periodic acid catalyzed by chromium ( III ) acetylacetonate. Tetrahedron Lett. 2003;44(12):2553–5.