Oxoammonium salt/NaClO2: An expedient, catalytic system for one-pot oxidation of primary alcohols to carboxylic acids with broad substrate applicability

Chemical Communications

Volumn , Issue 13, 2009, Pages 1739-1741

  Shibuya, Masatoshi ^a   Sato, Takahisa ^a   Tomizawa, Masaki ^a   Iwabuchi, Yoshiharu ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 62349100576     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b822944a     Document Type: Article

References (33)

1. M. F. Schlecht, in Comprehensive Organic Synthesis, eds., B. M. Trost,,, I. Fleming, and, S. V. Ley,, Pergamon, Oxford, 1991, vol 7, pp. 251-327
2. Modern Oxidation Methods, ed., J.-E. Bäckvall,, Wiley-VCH, Weinheim, Germany, 2004
3. R. W. Drugger J. A. Ragan D. H. Brown Ripin Org. Process Res. Dev. 2005 9 253
4. J. S. Carey D. Laffan C. Thomson M. T. Williams Org. Biomol. Chem. 2006 4 2337
5. S. Caron R. W. Dugger S. G. Ruggeri J. A. Ragan D. H. Brown Ripin Chem. Rev. 2006 106 2943
6. K. Bowden I. M. Heibron E. R. H. Jones B. C. L. Weedon J. Chem. Soc. 1946 39
7. E. J. Corey G. Schmidt Tetrahedron Lett. 1979 5 399
8. M. Zhao J. Li Z. Song R. Desmond D. M. Tschaen E. J. J. Grabowski P. J. Reider Tetrahedron Lett. 1998 39 5323
9. P. H. J. Carlsen T. Katsuki V. S. Martin K. B. Sharpless J. Org. Chem. 1981 46 3936
10. M. Schröder W. P. Griffith J. Chem. Soc., Chem. Commun. 1979 58
11. R. Noyori M. Aoki K. Sato Chem. Commun. 2003 1977
12. H. Tohma S. Takizawa T. Maegawa Y. Kita Angew. Chem., Int. Ed. 2000 39 1306
13. H. Tohma T. Maegawa S. Takizawa Y. Kita Adv. Synth. Catal. 2002 344 328
14. P. L. Anelli C. B. F. Montanari S. Quici J. Org. Chem. 1987 52 2559
15. J. B. Epp T. S. Widlanski J. Org. Chem. 1999 64 293
16. M. Zhao J. Li E. Mano Z. Song D. M. Tschaen E. J. J. Grabowski P. J. Reider J. Org. Chem. 1999 64 2564
17. M. Zhao J. Li E. Mano Z. J. Song D. M. Tschaen Org. Synth. 2004 81 195
18. A. Zanka Chem. Pharm. Bull. 2003 51 888
19. 2 does not oxidize nitroxyl radicals effectively
20. M. Shibuya M. Tomizawa I. Suzuki Y. Iwabuchi J. Am. Chem. Soc. 2006 128 8412
21. A. E. de Nooy A. C. Besemer H. van Bekkum Synthesis 1996 1153
22. R. A. Sheldon I. W. C. E. Arends Adv. Synth. Catal. 2004 1051
23. V. Golubev E. G. Roznzev N. B. Neiman Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1965 1989
24. T. Miyazawa T. Endo S. Shiihashi M. Ogawara J. Org. Chem. 1985 50 1332
25. J. M. Bobbitt M. C. L. Flores Heterocycles 1998 27 509
26. Z. Ma J. M. Bobbitt J. Org. Chem. 1991 56 6110
27. J. M. Bobbitt J. Org. Chem. 1998 63 9367
28. C. A. Kernag J. M. Bobbitt D. V. McGrath Tetrahedron Lett. 1999 40 1635
29. N. Merbouh J. M. Bobbitt C. Brückner J. Org. Chem. 2004 69 5116
30. J. M. Bobbitt N. Merbouh Org. Synth. 2005 82 80
31. M. Shibuya M. Tomizawa Y. Iwabuchi J. Org. Chem. 2008 73 4750
32. - has been observed after storage in a desiccator at ambient temperature for several months
33. Y. Iwabuchi J. Synth. Org. Chem. Jpn. 2008 66 1076