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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 9
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Original Articles

Oxidation of Alcohols and Pyridines by a Water-Soluble Polyoxometalate with Hydrogen Peroxide

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Pages 1211-1218 | Received 16 Aug 2011, Published online: 21 Feb 2013

REFERENCES

  • (a) Sheldon , R. A. ; Kochi , J. K. Metal-Catalyzed Oxidation of Organic Compounds ; Academic Press : New York , 1981 ; (b) Pybus , D. H. ; Sell , C. S. (Eds.) , The Chemistry of Fragrances ; RSC Paperbacks : Cambridge , 1999 ; (c) Fey , T. ; Fischer , H. ; Bachmann , S. ; Albert , K. ; Bolm , C. Silica-supported TEMPO catalysts: Synthesis and application in the Anelli oxidation of alcohols. J. Org. Chem. 2001, 66, 8154-8159; (d) Singh , R. P. ; Subbarao , H. N. ; Sukh , Dev. Organic reactions in a solid matrix–V: Silica-gel supported chromic acid reagents. Tetrahedron 1979, 35, 1789–1793 .
  • (a) Albini , A. Synthetic utility of amine N-oxides. Synthesis 1993 , 263 – 277 ; (b) Malkov , A. V. ; Bell , M. ; Castelluzzo , F. ; Kočovský , P. METHOX: A new pyridine N-oxide organocatalyst for the asymmetric allylation of aldehydes with allyltrichlorosilanes . Org. Lett. 2005 , 7 , 3219 – 3222 ; (c) Campeau , L.-C. ; Rousseaux , S. ; Fagnou , K. A solution to the 2-pyridyl organometallic cross-coupling problem: Regioselective catalytic direct arylation of pyridine N-oxides . J. Am. Chem. Soc. 2005 , 127 , 332 , 18020 – 18021 ; (d) Sarma , R. ; Karmakar , A. ; Baruah , J. B. Synthesis and characterization of pyridine N-oxide complexes of manganese, copper, and zinc . Inorg. Chim. Acta 2008 , 361 , 2081 – 2086 .
  • (a) Anastas , P. T. ; Bartlett , L. B. ; Kirchhoff , M. M. ; Williamson , T. C. The role of catalysis in the design, development, and implementation of green chemistry . Catal. Today. 2000 , 55 , 11 – 22 ; (b) Clark , J. H. Green chemistry: Challenges and opportunities . Green Chem. 1999 , 1 , 1 – 8 ; (c) van Vliet , M. C. A. ; Mandelli , D. ; Arends , I. W. C. E. ; Schuchardt , U. ; Sheldon , R. A. Alumina: A cheap, active, and selective catalyst for epoxidations with (aqueous) hydrogen peroxide . Green Chem. 2001 , 3 , 243 – 246 .
  • (a) Zhang , Z. ; Zhao , W. ; Ma , B. ; Ding , Y. The epoxidation of olefins catalyzed by a new heterogeneous polyoxometalate-based catalyst with hydrogen peroxide . Catal. Commun. 2010 , 12 , 318 – 322 ; (b) Zhang , Z. ; Zhang , F. ; Zhu , Q. ; Zhao , W. ; Ma , B. ; Ding , Y. Magnetically separable polyoxometalate catalyst for the oxidation of dibenzothiophene with H2O2 . J. Colloid Interf. Sci. 2011 , 360 , 189 – 194 .
  • Sloboda-Rozner , D. ; Alsters , P. L. ; Neumann , R. A water-soluble and “self-assembled” polyoxometalate as a recyclable catalyst for oxidation of alcohols in water with hydrogen peroxide . J. Am. Chem. Soc. 2003 , 125 , 5280 – 5281 .
  • Wang , J. ; Yan , L. ; Li , G. ; Wang , X. ; Ding , Y. ; Suo , J. Mono-substituted Keggin-polyoxometalate complexes as effective and recyclable catalyst for the oxidation of alcohols with hydrogen peroxide in biphasic system . Tetrahedron Lett. 2005 , 46 , 7023 – 7027 .
  • Zhao , W. ; Zhang , Y. ; Ma , B. ; Ding , Y. ; Qiu , W. Oxidation of alcohols with hydrogen peroxide in water catalyzed by recyclable Keggin-type tungstoborate catalyst . Catal. Commun. 2010 , 11 , 527 – 531 .
  • Ma , B. ; Zhang , Y. ; Ding , Y. ; Zhao , W. A water-soluble dilacunary silicotungstate as an effective catalyst for oxidation alcohols in water with hydrogen peroxide. Catal. Commun. 2010, 11, 853–857.
  • Ding , Y. ; Zhao , W. ; Song , W. ; Zhang , Z. ; Ma , B. Mild and recyclable catalytic oxidation of pyridines to N-oxides with H2O2 in water mediated by a vanadium-substituted polyoxometalate . Green Chem. 2011 , 13 , 1486 – 1489 .
  • (a) Kamata , K. ; Kotani , M. ; Yamaguchi , K. ; Hikichi , S. ; Mizuno , N. Olefin epoxidation with hydrogen peroxide catalyzed by lacunary polyoxometalate [γ-SiW10O34(H2O)2]4−. Chem. Eur. J. 2007 , 13 , 639 – 648 ; (b) Téazéa , A. ; Hervéa , G. ; Finke , R. G. ; Lyon , D. K. α -, β-, and γ-dodecatungstosilicic acids: Isomers and related lacunary compounds. Inorg. Synth. 1990 , 27 , 85 – 96 .
  • Gao , J. ; Chen , Y. ; Xi , Z. ; Cao , G. ; Gao , S. Epoxidation of propylene by using [π-C5H5NC16H33]3[PW4O16] as catalyst and with hydrogen peroxide generated by 2-ethylanthrahydroquinone and molecular oxygen . Appl. Catal. A: Gen. 2003 , 250 , 239 – 245 .
  • (a) Duncan , D. C. ; Chambers , R. C. ; Hecht , E. ; Hill , C. L. Mechanism and dynamics in the H3[PW12O40]-catalyzed selective epoxidation of terminal olefins by H2O2: Formation, reactivity, and stability of {PO4[WO(O2)2]4}3−. J. Am. Chem. Soc. 1995 , 117 , 681 – 691 ; (b) Grecley , N. M. ; Griffith , W. P. ; Laemmel , A. C. ; Nogueira , H. S. ; Parkin , B. C. Studies on polyoxo- and polyperoxo-metalates, part 5: Peroxide-catalysed oxidations with heteropolyperoxo-tungstates and -molybdates . J. Mol. Catal. A: Chem. 1997 , 117 , 185 – 198 ; (c) Gao , J. ; Chen , Y. ; Han , B. ; Feng , Z. ; Li , C. ; Zhou , N. ; Gao , S. ; Xi , Z. A spectroscopic study on the reaction-controlled phase transfer catalyst in the epoxidation of cyclohexene. J. Mol. Catal. A: Chem. 2004 , 210 , 197 – 204 ; (d) Ding , Y. ; Zhao , W. ; Hua , H. ; Ma , B. [π-C5H5N(CH2)15CH3]3[PW4O32]/H2O2/ethyl acetate/alkenes: A recyclable and environmentally benign alkenes epoxidation catalytic system . Green Chem. 2008 , 10 , 910 – 913 ; (e) Zhao , W. ; Ma , B. H. ; H. ; Zhang , Y. ; Ding , Y. Environmentally friendly and highly efficient alkenes epoxidation system consisting of [π-C5H5N(CH2)11CH3]3PW4O32/H2O2/ethyl acetate/olefin. Catal. Commun. 2008 , 9 , 2455 – 2459 .

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