Mild and efficient access to lithium alkanesulfinates based on oxaziridine-promoted oxidation of thiolates

Journal of Sulfur Chemistry

Volumn 30, Issue 3-4, 2009, Pages 338-345

  Caupène, Caroline ^a   Martin, Claudie ^a   Lemarié, Margareth ^a   Perrio, Stéphane ^a   Metzner, Patrick ^a  

^a 6 Bd du Maréchal Juin   (France)

Author keywords

Oxaziridine; OXidation; Sulfinate; Sulfone; Thiolate

Indexed keywords

LITHIUM;

ALKANETHIOLATES; OXAZIRIDINES; OXIDATION REACTIONS; SULFINATES; THIOLATES;

OXIDATION;

EID: 71149090332     PISSN: 17415993     EISSN: 17416000     Source Type: Journal    
DOI: 10.1080/17415990902903009     Document Type: Article

References (41)

1. (a) Davis, F.A.; Chen, B.-C.; Zhou, P. In Comprehensive Heterocyclic Chemistry III; Katritzky, A.R., Ramsden, C.A., Scriven, E.F.V., Taylor, R.J.K., Eds.; Elsevier: Amsterdam 2008; Vol.1; pp 559-621
2. (b) Davis, F.A. J. Org. Chem. 2006, 71, 8993-9003
3. (c) Davis, F.A.; Chen, B.C. Chem. Rev. 1992, 92, 919-14
4. (d) Davis, F.A.; Sheppard, A.C. Tetrahedron 1989, 45, 5703-5742.
5. (a) Sandrinelli, F.; Perrio, S.; Beslin, P. J. Org. Chem. 1997, 62, 8626-8627
6. (b) Sandrinelli, F.; Perrio, S.; Averbuch- Pouchot, M.-T. Org. Lett. 2002, 4, 3619-3622
7. (c) Sandrinelli, F.; Fontaine, G.; Perrio, S.; Beslin, P. J. Org. Chem. 2004, 69, 6916-6919
8. (d) Sandrinelli, F.; Boudou, C.; Caupène, C.; Averbuch-Pouchot, M.-T.; Perrio, S.; Metzner, P. Synlett. 2006, 3289-3293.
9. This heterocycle was more recently employed for the oxidation of a thiolate-ligated iron complex and a potassium alkanesulfinate: (a) Lugo-Mas, P.; Dey, A.; Xu, L.; Davin, S.D.; Benedict, J.; Kaminsky, W.; Hodgson, K.O.; Hedman, B.; Solomon, E.I.; Kovacs, J.A. J. Am. Chem. Soc. 2006, 128, 11211-11221
10. (b) Alves de Sousa, R.; Artaud, I. Tetrahedron 2008, 64, 2198-2206.
11. Boudou, C.; Bergès, M.; Sagnes, C.; Sopková-de Oliveira Santos J.; Perrio, S.; Metzner, P. J. Org. Chem. 2007, 72, 5403-5406.
12. For the oxaziridine-mediated oxidation of aromatic thiolates into sulfinates and successful application in 11C-chemistry, see: (a) Sandrinelli, F.; Perrio, S.; Beslin, P. Org. Lett. 1999, 1, 1177-1180
13. (b) Martin, C.; Sandrinelli, F.; Perrio, C.; Perrio, S.; Lasne, M.-C. J. Org. Chem. 2006, 71, 210-214.
14. (a) Patai, S., Ed. The Chemistry of Sulfinic Acids and their Derivatives - The Chemistry of Functional Groups; John Wiley & Sons: Chichester, 1990
15. (b) Pandya, R.; Murashima, T.; Tedeschi, L.; Barrett, A.G.M. J. Org. Chem. 2003, 68, 8274-8276
16. (c) Katritzky, A.R.; Rodriguez-Garcia, V.; Nair, S.K. J. Org. Chem. 2004, 69, 1849-1852
17. (d) Chan, W.Y.; Berthelette, C. Tetrahedron Lett. 2002, 43, 4537-4540
18. (e) De Vleeschauwer, M.; Gauthier, J.Y. Synlett. 1997, 375-377.
19. (f) Baskin, J.M.; Wang, Z. Tetrahedron Lett. 2002, 43, 8479-8483
20. (g) Pinnick, H.W.; Reynolds, M.A. J. Org. Chem. 1979, 44, 160-161
21. (h) Guan, H.; Laird, A.D.; Blake, R.A.; Tang, C.; Liang, C. Bioorg. Med. Chem. Lett. 2004, 14, 187-190.
22. Wu, J.-P.; Emeigh, J.; Su, X.-P. Org. Lett. 2005, 7, 1223-1225 and cited therein.
23. (a) Ramaiah, K.; Dubey, P.K.; Ramanatham, J. Indian J. Chem. 1999, 38B, 297-301
24. (b) Chen, Y.; Lai, Y.-H. Org. Lett. 2003, 5, 1067-1069
25. (c) Baskin, J.M.; Wang, Z. Tetrahedron Lett. 2002, 43, 8479-8483
26. (d) Beziane, A.; Terme, T.; Vanelle, P. Molecules 2005, 10, 289-294.
27. (a) Weinberger, R. Practical Capillary Electrophoresis, Academic Press, San Diego, 2000
28. (b) Riekkola, M.-L.; Wiedmer, S. K.; Valkó, I. E.; Sirén, H. J. Chromatogr. A 1997, 792, 13-35
29. (c) Téllez, A.; Fuguet, E.; Rosés, M. J. Chromatogr. A 2007, 1139, 143-151
30. (d) Shang, X.; Yuan, Z. Bioorg. Med. Chem. Lett. 2003, 13, 617-622.
31. Significant differences in chemical shifts are observed between sulfinate and sulfonate analogues. See for example: Gais, H.-J.; Eichelmann, H.; Spalthoff, N.; Gerhards, F.; Franck M.; Raabe, G. Tetrahedron: Asymmetry 1998, 9, 235-248.
32. Sulfinates are ambident nucleophiles. With soft electrophiles such as halides the alkylation occurs predominantly at sulfur to give sulfones: (a) Simpkins N.S. Sulphones in Organic Synthesis, Baldwin, J.E.; Magnus P.D., Eds.; Pergamon Press: Oxford, 1993;Vol. 10, pp. 11-15
33. (b) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Parisi, L.M. Synlett. 2003, 361-364.
34. García Ruano, J.L.; Alemán, J.; Fajardo, C.; Parra, A. Org. Lett. 2005, 7, 5493-5496.
35. Rothstein, E. J. Chem. Soc. 1934, 684-687.
36. Harpp, D.N.; Gleason, J.G.; Ash, D.K. J. Org. Chem. 1971, 36, 322-326.
37. Challenger, F.; Taylor, P.; Taylor, B. J. Chem. Soc. 1942, 48-55.
38. Gipstein, E.; Wellisch, E.; Sweeting, O. J. J. Org. Chem. 1964, 29, 207-209.
39. Barton, D.H.R.; Li, W.; Smith, J.A. Tetrahedron Lett. 1998, 39, 7055-7058.
40. Truce, W.E.; Milionis, J.P. J. Org. Chem. 1952, 17, 1529-1533.
41. Auret, B.J.; Boyd, D.R.; Henbest, H.B.; Ross, S. J. Chem. Soc. (C) 1968, 2371-2374.