Chemoselective sulfide oxidation mediated by bridged flavinium organocatalysts

Tetrahedron Letters

Volumn 51, Issue 17, 2010, Pages 2362-2365

  Marsh, Barrie J ^a   Carbery, David R ^a  

^a University of Bath Claverton Down   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BRIDGED COMPOUND; FLAVINIUM; HYDROGEN PEROXIDE; SULFIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; OXIDATION; REACTION OPTIMIZATION; REACTION TIME; SOLVENT EFFECT; STEREOCHEMISTRY;

EID: 77949571327     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.02.164     Document Type: Article

References (36)

1. For recent general reviews on organocatalysis, see:. Dondoni A., and Massi A. Angew. Chem., Int. Ed. 47 (2008) 4638-4660
2. Bertelsen S., and Jorgensen K.A. Chem. Soc. Rev. 38 (2009) 2178-2189
3. Buckley B.R. Annu. Rep. Prog. Chem. Sect. B: Org. Chem. 105 (2009) 113-128
4. MacMillan D.W.C. Nature 455 (2008) 304-308
5. For reviews of flavin-mediated transformations, see:. Gelalcha F.G. Chem. Rev. 107 (2007) 3338-3361
6. Imada Y., and Naota T. Chem. Recl. 7 (2007) 354-361
7. 2 oxidations within a green context, see:. Sheldon R.A. Chem. Commun. (2008) 3352-3365
8. Piera J., and Backvall J.-E. Angew. Chem., Int. Ed. 47 (2008) 3506-3523
9. Arends I.W.C.E. Angew. Chem., Int. Ed. 45 (2006) 6250-6252
10. Ten Brink G.-J., Arends I.W.C.E., and Sheldon R.A. Chem. Rev. 104 (2004) 4105-4123
11. Noyori R., Aoki M., and Sato K. Chem. Commun. (2003) 1977-1986
12. Grigoropoulou G., Clark J.H., and Elings J.A. Green Chem. 5 (2003) 1-7
13. Murahashi S., Oda T., and Masui Y. J. Am. Chem. Soc. 111 (1989) 5002-5003
14. Lindén A.A., Krüger L., and Bäckvall J.E. J. Org. Chem. 68 (2003) 5890-5896
15. Linden A.A., Hermanns N., Ott S., Krueger L., and Bäckvall J.E. Chem. Eur. J. 11 (2005) 112-119
16. Miller A.E., Bischoff J.J., Bizub C., Luminoso P., and Smiley S. J. Am. Chem. Soc. 108 (1986) 7773-7778
17. Imada Y., Iida H., Ono S., and Murahashi S. J. Am. Chem. Soc. 125 (2003) 2868-2869
18. Bergstad K., and Bäckvall J.E. J. Org. Chem. 68 (2003) 6650-6655
19. Shinkai S., Yamaguchi T., Manabe O., and Toda F. J. Chem. Soc., Chem. Commun. (1988) 1399-1401
20. Minidis A.B.E., and Bäckvall J.-E. Chem. Eur. J. 7 (2001) 297-302
21. Imada Y., Ohno T., and Naota T. Tetrahedron Lett. 48 (2007) 937-939
22. Li W.S., Zhang N., and Sayre L.M. Tetrahedron 57 (2001) 4507-4522
23. For selected recent examples of catalytic sulfoxidations, see:. Kinen C.O., Rossi L.I., and de Rossi R.H. J. Org. Chem. 74 (2009) 7132-7139
24. Ricoux R., Allard M., Dubuc R., Dupont C., Marechal J.D., and Mahy J.P. Org. Biomol. Chem. 7 (2009) 3208-3211
25. Hussain S., Bharadwaj S.K., Pandey R., and Chaudhuri M.K. Eur. J. Org. Chem. (2009) 3319-3322
26. Kamata K., Hirano T., and Mizuno N. Chem. Commun. (2009) 3958-3960
27. Wu Y., Liu J., Li X., and Chan A.S.C. Eur. J. Org. Chem. (2009) 2607-2610
28. Mueller N.J., Stueckler C., Hall M., Macheroux P., and Faber K. Org. Biomol. Chem. 7 (2009) 1115-1119
29. Cojocariu A.M., Mutin P.H., Dumitriu E., Fajula F., Vioux A., and Hulea V. Chem. Commun. (2008) 5357-5359
30. Gamelas C.A., Lourenco T., Pontes da Costa A., Simplicio A.L., Royo B., and Romao C.C. Tetrahedron Lett. 49 (2008) 4708-4712
31. Noguchi T., Hirai Y., and Kirihara M. Chem. Commun. (2008) 3040-3042
32. Matsumoto K., Yamaguchi T., and Katsuki T. Chem. Commun. (2008) 1704-1706
33. Kienle M., Argyrakis W., Baro A., and Laschat S. Tetrahedron Lett. 49 (2008) 1971-1974
34. 2 (35% wt, 37 μl, 1.75 equiv) and shaken vigourously until the solution attained homogeneity. Spectra were recorded every 2 min for 20 min or until conversion had reached 20%. Conversion was determined by making a comparison of the integrals for the S-Me and (O)S-Me signals from the sulfide and sulfoxide, respectively.
35. 4, filtered and the solvent removed in vacuo to give the desired product as a white solid (62 mg, 95%) without the need for further purification.
36. Žurek J., Cibulka R., Dvořáková H., and Svoboda J. Tetrahedron Lett. 51 (2010) 1083-1086