Abstract
A simple and efficient method for the selective oxidation of alcohols to ketones using trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane at room temperature is developed. The reactions were smoothly proceeded under catalyst-free conditions to provide ketones in quantitative yields within short reaction times. Also, this method is compatible with many functional groups including aldehydes, olefins, halogens, amines and esters.
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References
R.A. Sheldon, J.K. Kochi, Metal Catalyzed Oxidations of Organic Compounds (Academic Press, London, 1981)
M. Hudlicky, Oxidation in Organic Chemistry (Am. Chem. Soc., Washington, DC, 1990)
J. Muzart, Tetrahedron 59, 5789 (2003)
S. Pääkkönen, J. Pursiainen, M. Lajunen, Tetrahedron Lett. 51, 6695 (2010)
V.B. Sharma, S.L. Jain, B. Sain, J. Mol. Cat. A: Chem. 212, 55 (2004)
V.B. Sharma, S.L. Jain, B. Sain, J. Mol. Cat. A: Chem. 227, 47 (2005)
C. Kuhakarn, K. Kittigowittana, M. Pohmakotr, V. Reutrakul, Tetrahedron 61, 8995 (2005)
S.L. Jain, V.B. Sharma, B. Sain, Tetrahedron 62, 6841 (2006)
S.V. Ley, A. Madin, in Comprehensive Organic Synthesis, 7, ed. by B.M. Trost, I. Fleming (Pergamon, Oxford, 1991), pp. 305–327
K. Kaczorowska, Z. Kolarska, K. Mitka, P. Kowalski, Tetrahedron 61, 8315 (2005). and references cited therein
M. Patek, B. Drake, M. Lebel, Tetrahedron Lett. 36, 2227 (1995)
S. Sylvian, A. Wanger, C. Mioskowosky, Tetrahedron Lett. 38, 1043 (1997)
R. Noyori, M. Aoki, K. Sato, Chem. Commun. 16, 1977 (2003)
B.S. Lane, K. Burgess, Chem. Rev. 103, 2457 (2003)
A.J. Catino, R.E. Forslund, H.R. Yao, K.M. Frank, D.A. Bennet, J. Am. Chem. Soc. 122, 1729 (2000)
B.S. Lane, K. Burgess, Chem. Rev. 103, 2456 (2003)
K. Sato, M. Hyodo, M. Aoki, X.-Q. Zheng, R. Noyori, Tetrahedron 57, 2469 (2001)
C.W. Jones, Applications of Hydrogen Peroxides and Derivatives (Royal Society of Chemistry, Cambridge, 1999)
G. Srukul, Catalytic Oxidations with Hydrogen Peroxides as Oxidant (Kluwer Academic, Dordreecht, 1992)
M. Matteucci, G. Bhalay, M. Bradley, Org. Lett. 5, 235 (2003)
O. Bortolini, D.F. Furia, G. Modena, R. Seraglia, J. Org. Chem. 50, 2688 (1985)
M.R. Berenguer, O.J. Campon, L. Coppi, Chem. Abstr. 135, 242230 (2003)
H. Hashimoto, T. Ural, EP Patent 1277752A1
H. Hashimoto, T. Ural, Chem. Abstr. 135, 357923 (2003)
B. Kagan, Chem. Rev. 102, 19805 (2002)
S. Kobayashi, Lanthanides: Chemistry and Use in Organic Synthesis (Springer, Berlin, 1999)
L.B. Young, W.S. Trahanovsky, J. Org. Chem. 32, 2349 (1967)
Ho, T.-L. Synthesis. 12, 936 (1978)
N. Al-Haq, A.C. Sullivan, J.R.H. Wilson, Tetrahedron Lett. 44, 769 (2003)
For a review, see: T. Kratz, W. Zeiss, In Peroxide Chemistry; Adam, W., Ed.; Wiley-VCH: Weinheim, (2000); pp 41–59
For leading examples, see: J. Iskara, D. Bonnet-Delpon, J. P. Begue, Tetrahedron Lett. 44, 6309 (2003)
K. Tsuchiya, Y. Hamada, A. Masuyama, M. Nojima, K.J. McCullough, H.-S. Kim, Y. Shibata, Y. Wataya, Tetrahedron Lett. 40, 4077 (1999)
J.J.P. Selvam, V. Suresh, K. Rajesh, D.C. Babu, N. Suryakiran, Y. Venkateswalu, Tetrahedron Lett. 49, 3463 (2008)
K. Zmitek, M. Zupan, S. Stavber, J. Iskra, Org. Lett. 8, 2491 (2006)
A. Rieche, C. Bischoff, Chem. Ber. 95, 77 (1962)
D. Azarifar, Z. Najminejad, K. Khosravi, Synth. Commun. (2013), In press, DOI 101080/00397911.2011.610549
D. Azarifar, K. Khosravi, Synlett. 18, 2755 (2010)
D. Azarifar, K. Khosravi, Z. Najminejad, K. Soleimani, Heterocycles 81, 2855 (2010)
D. Azarifar, K. Khosravi, F. Soleimani, Synthesis 2553 (2009)
D. Azarifar, K. Khosravi, F. Soleimanei, F. Molecules 15, 1433 (2010)
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The authors wish to thank the Buali Sina University research council for the financial support.
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Azarifar, D., Najminejad, Z. & Khosravi, K. Catalyst-free selective oxidation of alcohols to carbonyls using trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane as an efficient oxidant. J IRAN CHEM SOC 10, 979–983 (2013). https://doi.org/10.1007/s13738-013-0235-3
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DOI: https://doi.org/10.1007/s13738-013-0235-3