Oxidation of allylic alcohols, amines, and sulfides mediated by assembled triphase catalyst of phosphotungstate and non-cross-linked amphiphilic copolymer

Tetrahedron

Volumn 60, Issue 18, 2004, Pages 4087-4096

  Yamada, Yoichi M A ^a   Tabata, Hidetsugu ^a   Ichinohe, Masato ^a   Takahashi, Hideyo ^a   Ikegami, Shiro ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

Catalysis; Oxidation; Polymer support; Self assembly; Tungsten and compounds

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL ALCOHOL; ALLYL COMPOUND; AMINE; AMMONIA; COPOLYMER; IMINE; PHOSPHOTUNGSTIC ACID; POLY(N ISOPROPYLACRYLAMIDE); SULFIDE;

AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CROSS LINKING; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SUPRAMOLECULAR CHEMISTRY;

EID: 1842713118     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.02.072     Document Type: Article

References (67)

1. Anastas P.T., Warner J.C. Green chemistry: theory and practice. 1998;Oxford University Press, Oxford.
2. Anastas P.T., Heine L.G., Williamson T.C. Green chemical syntheses and processes: recent advances in chemical processing. 2001;American Chemical Society, Ohio.
3. Tundo P., Anastas P., Black D.S., Breen J., Collins T., Memoli S., Miyamoto J., Polyakoff M., Tumas W. Pure Appl. Chem. 72:2000;1207-1228.
4. Noyori R., Aoki M., Sato K. Chem. Commun. 2003;1977.
5. Regen S.L. Angew. Chem. Int. Ed. 18:1979;421-429.
6. Centi G., Cavani F., Trifiro F. Selective oxidation by heterogeneous catalysis (fundamental and applied catalysis). 2000;Kluwer Academic, Norwell, MA.
7. Hodnett K. Heterogeneous catalytic oxidation. 2000;Wiley, New York.
8. Bunin B.A. The combinatorial index. 1998;Academic, San Diego.
9. Moore J.A. Reactions on polymers. 1973;Redel, Boston.
10. Blossey E.C., Neckers D.C. Solid phase synthesis. 1975;Dowden, Hutchinson and Ross, Pennsylvania.
11. Corma A., García H. Chem. Rev. 102:2002;3837-3892.
12. Yamada Y.M.A., Ichinohe M., Takahashi H., Ikegami S. Org. Lett. 3:2001;1837-1841.
13. Yamada Y.M.A., Ichinohe M., Takahashi H., Ikegami S. Tetrahedron Lett. 43:2002;3431-3434.
14. Yamada Y.M.A., Takeda K., Takahashi H., Ikegami S. Org. Lett. 4:2002;3371-3374.
15. Yamada Y.M.A., Takeda K., Takahashi H., Ikegami S. J. Org. Chem. 68:2003;7733-7741.
16. Yamada Y.M.A., Takeda K., Takahashi H., Ikegami S. Tetrahedron. 60:2004;. proceeding article. See doi: 10.1016/j.tet.2004.02.068.
17. Yamada Y.M.A., Tabata H., Takahashi H., Ikegami S. Synlett. 2002;2031-2034.
18. Partial results were reported as communications, see Refs. 4a and 4d.
19. Jacobs and co-workers reported the Amberlite IRA-900-supported Venturello catalyst converted into NO3- was effective for the enhancement of selectivity of epoxidation, see: Villa A.L., Sels B.F., de Vos D.E., Jacobs P.A. J. Org. Chem. 64:1999;7267-7270.
20. Ishii Y., Yamawaki K., Ura T., Yamada H., Yoshida T., Ogawa M. J. Org. Chem. 53:1988;3587-3593.
21. Addition of 1 to poly(N-isopropylacrylamide) afforded no precipitates. This result indicated that the existence of the ammonium salt units in 2 was essential for cross-linking the polymers through phosphotungstates.
22. Massart R., Contant R., Fruchart J.-M., Ciabrini J.-P., Fournier M. Inorg. Chem. 16:1977;2916-2921.
23. Ishii Y., Tanaka H., Nishiyama Y. Chem. Lett. 1994;1-4.
24. Keggin J.F., Proc R. Proc. R. Soc. London, Ser. A. 144:1934;75-100.
25. Brown G.M., Noe-Spirlet M.-R., Busing W.R., Levy H.A. Acta Crystallogr. B. 33:1977;1038-1046.
26. For examples of the epoxidation by homogeneous tungsten catalysts, see: Ogata Y., Sawaki Y. Mijs W.J., De Jonge C.R.H.I. Organic syntheses by oxidation with metal compounds. 1986;839-876 Plenum Press, New York.
27. Sato K., Aoki M., Noyori R. Science. 281:1998;1646-1647.
28. Venturello C., Gambaro M. J. Org. Chem. 56:1991;5924-5931.
29. Venturello C., Gambaro M. Synthesis. 1989;295-297.
30. Bortolini O., Conte V., Di Furia F., Modena G. Di Furia. J. Org. Chem. 51:1986;2661-2663.
31. Recent attempts to improve the drawbacks on polymer-supported tungsten catalysts for the epoxidation, see: Villa A.L., Sels B.F., De Vos D.E., Jacobs P.A. J. Org. Chem. 64:1999;7267-7270.
32. Hoegaerts D., Sels B.F., de Vos D.E., Verpoort F., Jacobs P.A. Catal. Today. 60:2000;209-218.
33. Gelbard G., Breton F., Quenard M., Sherrington D.C. J. Mol. Catal. A: Chem. 153:2000;7-18.
34. Sakamoto T., Pac C. Tetrahedron Lett. 41:2000;10009-10012.
35. Briot E., Piquemal J.-Y., Vennat M., Brégeault J.-M., Chottard G., Manoli J.-M. J. Mater. Chem. 10:2000;953-958.
36. Ichihara J. Tetrahedron Lett. 42:2001;695-697.
37. De Bos D.E., Wahlen J., Sels B.F., Jacobs P.A. Synlett. 2002;367-380. Also, see: Ref. 6.
38. It was reported that pH control in aqueous media was important for the tungsten-catalyzed epoxidation, see Refs. 12d, 12e and 13b.
39. Haines A.H. Methods for the oxidation of organic compounds. 1985;Academic, London.
40. For examples of the oxidation of amines by homogeneous tungsten catalysts; For a review, see: (a) Herrmann W.A., Fridgen J., Haider J.J. Adam W. Peroxide chemistry. 2000;406-432 Wiley, Weinheim.
41. For examples, see: (b) Ogata Y., Tomizawa K., Maeda H. Bull. Chem. Soc. Jpn. 53:1980;285-286.
42. Murahashi S., Mitsui H., Shiota T., Tsuda T., Watanabe S. J. Org. Chem. 55:1990;1736-1744.
43. Murahashi S., Oda T., Sugahara T., Masui Y. J. Org. Chem. 55:1990;1744-1749.
44. Sakaue S., Sakata Y., Ishii Y. Chem. Lett. 1992;289-292.
45. Marcantoni E., Petrini M., Polimanti O. Tetrahedron Lett. 36:1995;3561-3562.
46. Ballistreri F.P., Barbuzzi E.G.M., Tomaselli G.A. J. Org. Chem. 61:1996;6381-6387.
47. For recent developments and improvements for the oxidation of amines, see: (a) Reddy J.S., Jacobs P.A. J. Chem. Soc. Perkin Trans. 1. 22:1993;2665-2666.
48. Joseph R., Sudalai A., Ravindranathan T. Synlett. 11:1995;1177-1178.
49. Joseph R., Ravindranathan T., Sudalai A. Tetrahedron. Lett. 36:1995;1903-1904.
50. Delaude L., Laszlo P. J. Org. Chem. 61:1996;6360-6370.
51. Dewkar G.K., Nikalje M.D., Ali I.S., Paraskar A.S., Jagtap H.S., Sudalai S. Angew. Chem. Int. Ed. 40:2001;405-408.
52. 2 aqueous solution was less successful because dimerization of the substrates occurred. Besides, recycling of PWAA in case of 9a was not efficient to afford 10a in lower yield.
53. 2 under identical conditions, isomerizations were hardly observed.
54. For examples of the oxidation of sulfides to sulfones by homogeneous tungsten catalysts, see: (a) Schultz H.S., Freyermuth H.B., Buc S.R. J. Org. Chem. 28:1963;1140-1142.
55. Stec Z., Zawadiak J., Skibinski A., Pastuch G. Polish J. Chem. 70:1996;1121-1123.
56. Neumann R., Juwiler D. Tetrahedron. 52:1996;8781-8788.
57. Gresley N.M., Griffith W.P., Laemmel A.C., Nogueira H.I.S., Perkin B.C. J. Mol. Catal. 117:1997;185-198.
58. Collins F.M., Lucy A.R., Sharp C. J. Mol. Catal. 117:1997;397-403.
59. Yasuhara Y., Yamaguchi S., Ichihara J., Nomoto T., Sasaki Y. Phosphorus Res. Bull. 11:2000;43-46.
60. Sato K., Hyodo M., Aoki M., Zheng X.-Q., Noyori R. Tetrahedron. 57:2001;2469-2476. Also, see: Ref. 9.
61. For recent developments and improvements for the oxidation of sulfides to sulfones, see: (a) Dell'Anna M.M., Mastrorilli P., Nobile C.F. J. Mol. Catal. A: Chem. 108:1996;57-62.
62. Alcon M.J., Corma A., Iglesias M., Sanchez F. J. Mol. Catal. A: Chem. 178:2002;253-266.
63. Noyori et al. reported that the oxidation of sulfides to sulfoxides proceeded efficiently in hydrogen peroxide without catalysts, so that we have not examined the selective oxidation to sulfoxide. See Ref. 19g.
64. Baudin J.B., Hareau G., Julia S.A., Ruel O. Tetrahedron Lett. 32:1991;1175-1178.
65. Kondo K., Tunemoto D. Tetrahedron Lett. 17:1975;1397-1400.
66. Caton M.P.L., Coffee E.C.J., Watkins G.L. Tetrahedron Lett. 9:1972;773-774.
67. 3- maintained the structure closed to Keggin unit after treatment with hydrogen peroxide. See Ref. 10.