Esters are known as one of the most fundamental chemical
moieties and also essentially useful components, especially for medicinal agents. Herein, using benzaldehyde and its
derivatives as starting materials, Oxone-mediated preparation of ester derivatives in the presence of a catalytic amount of indium(III) triflate is
described. Alcohols with various chain lengths, which functioned as solvents and substrates, were examined. Overall,
the oxidative esterification starting with
benzaldehyde derivatives possessing electron withdrawing groups proceeded
smoothly and gave sufficient yields, in comparison to the reactions with the
derivatives having electron donating groups.
References
[1]
Chang, Q., Chow, M.S.S. and Zuo, Z. (2009) Studies on the Influence of Esterase Inhibitor to the Pharmacokinetic Profiles of Oseltamivir and Oseltamivir Carboxylate in Rats Using an Improved LC/MS/MS Method. Biomedical Chromatography, 23, 852-857. https://doi.org/10.1002/bmc.1195
[2]
Fregnan, G.B. and Torsello, A.L. (1975) Topical Anti-Inflammatory Activity of Dexamethasone 17-Valerate and Other Corticosteroids. Current Therapeutic Researc, 17, 375-381.
[3]
Fujiwara, K., Ajioka, H. and Miyake, H. (1984) Anti-Inflammatory Effect of Dexamethasone 17,21-Dipropionate (THS-101) (2). Oyo Yakuri-Pharmacometrics, 28, 653-661.
[4]
Mineno, T. and Kansui, H. (2006) High Yielding Methyl Esterification Catalyzed by Indium(III) Chloride. Chemical & Pharmaceutical Bulletin, 54, 918-919. https://doi.org/10.1248/cpb.54.918
[5]
Mineno, T. and Miller, M.J. (2003) Stereoselective Total Synthesis of Racemic BCX-1812 (RWJ-270201) for the Development of Neuraminidase Inhibitors as Anti-Influenza Agents. The Journal of Organic Chemistry, 68, 6591-6596. https://doi.org/10.1021/jo034316b
[6]
Mineno, T., Sakai, M., Ubukata, A., Nakahara, K., Yoshimitsu, H. and Kansui, H. (2013) The Effect of Indium Triflate(III) in Oxone-Mediated Oxidative Methyl Esterification of Aldehydes. Chemical & Pharmaceutical Bulletin, 61, 870-872. https://doi.org/10.1248/cpb.c13-00072
[7]
Marcotullio, M.C., Epifano, F. and Curini, M. (2003) Recent Advances in the Use of Oxone® in Organic Synthesis. Trends in Organic Chemistry, 10, 21-34.
[8]
Hussain, H., Green, I.R. and Ahmed, I. (2013) Journey Describing Applications of Oxone in Synthetic Chemistry. Chemical Reviews, 113, 3329-3371. https://doi.org/10.1021/cr3004373
[9]
Armstrong, A., Ahmed, G., Garnett, I. and Goacolou, K. (1997) Pyrrolidine-Derived Iminium Salts as Catalysts for Alkene Epoxidation by Oxone. Synlett, No. 9, 1075-1076. https://doi.org/10.1055/s-1997-1542
[10]
Denmark, S.E., Wu, Z., Crudden, C.M. and Matsuhashi, H. (1997) Catalytic Epoxidation of Alkenes with Oxone, 2. Fluoro Ketones. The Journal of Organic Chemistry, 62, 8288-8289. https://doi.org/10.1021/jo971781y
[11]
Hashimoto, N. and Kanda, A. (2002) Practical and Environmentally Friendly Epoxidation of Olefins Using Oxone. Organic Process Research & Development, 6, 405-406. https://doi.org/10.1021/op025511f
[12]
Armstrong, A. (2004) Amine-Catalyzed Epoxidation of Alkenes: A New Mechanism for the Activation of Oxone. Angewandte Chemie International Edition, 43, 1460-1462. https://doi.org/10.1002/anie.200301716
[13]
Trost, B.M. and Curran, D.P. (1981) Chemoselective Oxidation of Sulfides to Sulfones. Tetrahedron Letters, 22, 1287-1290. https://doi.org/10.1016/S0040-4039(01)90298-9
[14]
Mahajan, N.S., Jadhav, R.L., Pimpodkar, N.V., Dias, R.J. and Manikrao, A.M. (2009) Green Solid Oxidation of Silfides to Sulfones Using Oxone and Biological Evaluation. Asian Journal of Chemistry, 21, 5415-5420.
[15]
Hirano, M., Oose, M. and Morimoto, T. (1991) A Novel Synthesis of Lactones by the Oxidation of Alicyclic Ketones with Oxone in Aprotic Solvent in the Pressure of Wet-Alumina. Chemistry Letters, 331-332. https://doi.org/10.1246/cl.1991.331
[16]
Chrobok, A. (2010) The Baeyer-Villiger Oxidation of Ketones with Oxone® in the Presence of Ionic Liquids as Solvents. Tetrahedron, 66, 6212-6216. https://doi.org/10.1016/j.tet.2010.05.091
[17]
Mineno, T., Yoshino, S. and Ubukata, A. (2014) Oxone-Mediated Oxidative Esterification of Heterocyclic Aldehydes Using Indium(III) Triflate. Green and Sustainable Chemistry, 4, 20-23. https://doi.org/10.4236/gsc.2014.41004
[18]
Travis, B.R., Silvakumar, M., Hollist, G.O. and Borhan, B. (2003) Facile Oxidation of Aldehydes to Acids and Esters with Oxone. Organic Letters, 5, 1031-1034. https://doi.org/10.1021/ol0340078
[19]
Abraham, R.J., Bardsley, B., Mobli, M. and Smith, R.J. (2005) 1H Chemical Shifts in NMR. Part 21+—Prediction of the 1H Chemical Shifts of Molecules Containing the Ester Group: A Modelling and ab Initio Investigation. Magnetic Resonance in Chemistry, 43, 3-15. https://doi.org/10.1002/mrc.1491
[20]
Sequin, U. (1981) Carbon-13 NMR Spectral Differences between Corresponding Methyl Esters, Phenyl Esters and 2-Substituted Chromones. Helvetica Chimica Acta, 64, 2654-2664. https://doi.org/10.1002/hlca.19810640824
[21]
Schmidt, A., Habeck, T., Snovydovych, B. and Eisfeld, W. (2007) Addition Reactions and Redox Esterifications of Carbonyl Compounds by N-Heterocyclic Carbenes of Indazole. Organic Letters, 9, 3515-3518. https://doi.org/10.1021/ol0713739
[22]
Gowrisankar, S., Neumann, H. and Beller, M. (2011) General and Selective Palladium-Catalyzed Oxidative Esterification of Alcohols. Angewandte Chemie International Edition, 50, 5139-5143. https://doi.org/10.1002/anie.201008035
[23]
Liu, Q., Li, G., He, J., Liu, J., Li, P. and Lei, A. (2010) Palladium-Catalyzed Aerobic Oxidative Carbonylation of Arylboronate Esters under Mild Conditions. Angewandte Chemie International Edition, 49, 3371-3374. https://doi.org/10.1002/anie.201000460
[24]
Hu, Y., Liu, J., Lu, Z., Luo, X., Zhang, H., Lan, Y. and Lei, A. (2010) Base-Induced Mechanistic Variation in Palladium-Catalyzed Carbonylation of Aryl Iodides. Journal of the American Chemical Society, 132, 3153-3158. https://doi.org/10.1021/ja909962f
[25]
Mercadante, M.A. and Leadbeater, N.E. (2011) Continuous-Flow, Palladium-Catalysed Alkoxycarbonylation Reactions Using a Prototype Reactor in Which It Is Possible to Load Gas and Heat Simultaneously. Organic and Biomolecular Chemistry, 9, 6575-6578. https://doi.org/10.1039/c1ob05808h
[26]
Yamamoto, Y. (2010) The First General and selective Palladium(II)-Catalyzed Alkoxycarbonylation of Arylboronates: Interplay among Benzoquinone-Ligated Palladium(0) Complex, Organoboron, and Alcohol Solvent. Advanced Synthesis & Catalysis, 352, 478-492. https://doi.org/10.1002/adsc.200900836
[27]
Shang, R., Fu, Y., Li, J.-B., Zhang, S.-L., Guo, Q.-X. and Liu, L. (2009) Synthesis of Aromatic Esters via Pd-Catalyzed Decarboxylative Coupling of Potassium Oxalate Monoesters with Aryl Bromides and Chlorides. Journal of the American Chemical Society, 131, 5738-5739. https://doi.org/10.1021/ja900984x
[28]
Kiran, Y.B., Ikeda, R., Sakai, N. and Konakahara, T. (2010) Single-Step Conversion of Electron-Deficient Aldehydes into the Corresponding Esters in Aqueous Alcohols in the Presence of Iodine and Sodium Nitrite. Synthesis, No. 2, 276-282. https://doi.org/10.1055/s-0029-1217121
[29]
Hashmi, A.S.K., Lothschuetz, C., Ackermann, M., Doepp, R., Anantharaman, S., Marchetti, B., Bertagnolli, H. and Rominger, F. (2010) Gold Catalysis: In Situ EXAFS Study of Homogeneous Oxidative Esterification. Chemistry: A European Journal, 16, 8012-8019. https://doi.org/10.1002/chem.200903450
