Efficient oxidation of alcohols electrochemically mediated by azabicyclo-N-oxyls

Tetrahedron Letters

Volumn 49, Issue 1, 2008, Pages 48-52

  Demizu, Yosuke ^a   Shiigi, Hirofumi ^b   Oda, Takahisa ^a   Matsumura, Yoshihiro ^a   Onomura, Osamu ^a  

^a NAGASAKI UNIVERSITY   (Japan)

^b TOKUYAMA CORPORATION   (Japan)

Author keywords

Alcohol; Aldehyde; Ketone; Nitroxyl radical; Oxidation

Indexed keywords

ALCOHOL; BICYCLO COMPOUND; KETONE DERIVATIVE;

ALCOHOL OXIDATION; ARTICLE; ELECTROCHEMICAL ANALYSIS; ELECTROCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 36549021985     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.016     Document Type: Article

References (35)

1. Recent reviews:. Noyori R., Aoki M., and Sato K. Chem. Commun. (2003) 1977-1980
2. Irie R., and Katsuki T. Chem. Record 4 (2004) 96-109
3. Mallat T., and Baiker A. Chem. Rev. 104 (2004) 3037-3058
4. Schultz M.J., and Sigman M.S. Tetrahedron 62 (2006) 8227-8241
5. Representative recent reviews:. de Nooy A.E.J., Besemer A.C., and van Bekkum H. Synthesis (1996) 1153-1174
6. Sakai T. Yuki Gosei Kagaku Kyokaishi 60 (2002) 1215-1218
7. Sheldon A.R., and Arends W.C.E.I. Adv. Synth. Catal. 346 (2004) 1051-1076
8. Semmelhack M.F., Chou C.S., and Cortes D.A. J. Am. Chem. Soc. 105 (1983) 4492-4494
9. Osa T., Akiba U., Segawa I., and Bobbitt J.M. Chem. Lett. 8 (1988) 1423-1426
10. Inokuchi T., Matsumoto S., and Torii S. J. Org. Chem. 56 (1991) 2416-2421
11. Yoshida T., Kuroboshi M., Oshitani J., Gotoh K., and Tanaka H. Synlett (2007) 2691-2694
12. Using modified TEMPO:. Kashiwagi Y., Kurashima F., Chiba S., Anzai J., Osa T., and Bobbitt J.M. Chem. Commun. (2003) 114-115
13. Kubota J., Ido T., Tanaka H., Uchida T., and Shimamura K. Tetrahedron 62 (2006) 4769-4773
14. Shibuya M., Tomizawa M., Suzuki I., and Iwabuchi Y. J. Am. Chem. Soc. 128 (2006) 8412-8413
15. Mahoney L.R., Mendenhall G.D., and Ingold K.U. J. Am. Chem. Soc. 95 (1973) 8610
16. Sümmermann W., and Deffner U. Tetrahedron 31 (1975) 593-596
17. Passat A., and Ronzaud J. Tetrahedron 32 (1976) 239-244
18. Aurich H.G., and Czepluch H. Tetrahedron Lett. 14 (1978) 1187-1190
19. Nelsen S.F., Kessel C.R., and Brien D.J. J. Am. Chem. Soc. 102 (1980) 702-711
20. Boldwell F.G., and Liu W.-Z. J. Am. Chem. Soc. 118 (1996) 10819-10823
21. Bredt J., Thouet H., and Schnitz J. Liebigs Ann. 437 (1924) 1-13
22. We found only one literature for chemical oxidation:. Graetz B., Rychnovsky S., Leu W., Farmer P., and Lin R. Tetrahedron: Asymmetry 16 (2005) 3584-3598
23. Shono T., Matsumura Y., Tsubata K., Sugihara Y., Yamane S.-I., Kanazawa T., and Aoki T. J. Am. Chem. Soc. 104 (1982) 6697-6703
24. Shono T., Matsumura Y., Uchida K., and Kobayashi H. J. Org. Chem. 50 (1985) 3243-3245
25. Mendenhall G.D., and Ingold K.U. J. Am. Chem. Soc. 95 (1973) 2963-2971
26. 14ClNO, 175.0764; found, 175.0781.
27. Relative stereoconfiguration of 13 was determined by the X-ray analysis. Crystallographic data for this structure have been deposited with the Cambridge Crystallographic Data Centre as Supplementary Publication Number CCDC 663222. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK; fax: +44(0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk.
28. 3 as a reference electrode. Concentration of (9 + 10): 1.0 mM. Scan rate: 10 mV/s. Other N-oxyls (11 + 12), 13, 14, and 17 were represented by the similar reversible wave patterns.
29. 4 and the solvent removed under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt = 20:1) to afford 16 (66 mg, 99% yield) as a colorless oil.
30. 16 Since isolated 17 was somewhat unstable, it gradually changed into the corresponding N-hydroxylamine even at -20 °C.
31. Olivo H.F., Peeples T.L., Ríos M.-Y., Velázquez F., Kim J.-W., and Narang S. J. Mol. Catal. B: Enzym. 21 (2003) 97-105
32. 4 and the solvent removed under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt = 20:1) to afford 33 (77 mg, 99% yield) as a colorless oil.
33. Lei M., Hu R.-J., and Wang Y.-G. Tetrahedron 62 (2006) 8928-8932
34. Recently, some methods for highly efficient chemical oxidation of sterically hindered secondary alcohols using TEMPO or its analogs have been reported:. Bobbitt J.M. J. Org. Chem. 63 (1998) 9367-9374
35. Zhao X.-F., and Zhang C. Synthesis (2007) 551-557