A mild protocol for the deoxygenation of α-hydrogen-containing sulfoxides to the corresponding sulfides

Tetrahedron Letters

Volumn 45, Issue 27, 2004, Pages 5193-5195

  Bhatia, Gurpreet S ^a   Graczyk, Piotr P ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Deoxygenation; Sulfides; Sulfoxides

Indexed keywords

HYDROGEN; SULFIDE; SULFOXIDE;

ARTICLE; DEOXYGENATION; METHODOLOGY; OXIDATION; SYNTHESIS; TECHNIQUE;

EID: 2942515228     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.049     Document Type: Article

References (38)

1. Walker A.J. Tetrahedron: Asymmetry. 3:1992;961-998
2. Posner G.H. Patai S., Rappoport Z., Stirling C.J.M. The Chemistry of Sulfones and Sulfoxides. 1988;823-849 Wiley, New York
3. Solladie G. Morrison J.D. Asymmetric Synthesis. Vol. 2:1983;157-199 Academic, New York
4. Barbachyn M.R., Johnson C.R. Morrison J.D., Scott J.W. Asymmetric Synthesis. Vol. 4:1984;227-261 Academic, Orlando
5. Drabowicz J., Numata T., Oae S. Org. Prep. Proced. Int. 9:1977;63-83
6. Drabowicz J., Togo H., Mikolajczyk M., Oae S. Org. Prep. Proced. Int. 16:1984;171-198
7. Kukushkin V.Y. Russ. Chem. Rev. 59:1990;844-852
8. Kukushkin V.Y. Coord. Chem. Rev. 139:1995;375-407
9. Madesclaire M. Tetrahedron. 44:1988;6537-6580
10. Smiles S., Gazdar M. J. Chem. Soc., Abstr. 97:1911;2248-2253
11. Gilman H., Eisch J. J. Am. Chem. Soc. 77:1955;3862-3865
12. Zinke T., Baeumer J. Justus Liebigs Ann. Chem. 416:1918;86-112
13. Mehmet Y., Hyne J.B. Phosphorus Sulfur. 1:1976;47-54
14. Wallace T.J. Chem. Ind. (London). 1964;501-502
15. Mikolajczyk M. Angew. Chem., Int. Ed. Engl. 5:1966;419
16. Kukolja S., Lammert S.R., Gleissner M.R.B., Ellis A.I. J. Am. Chem. Soc. 98:1976;5040-5041
17. Bird C.W. J. Chem. Soc. (C). 1968;1230-1232
18. Baechler R.D., Daley S.K. Tetrahedron Lett. 19:1978;101-104
19. Chan T.H., Melnyk A., Harpp D.N. Tetrahedron Lett. 10:1969;201-204
20. Naumann K., Zon G., Mislow K. J. Am. Chem. Soc. 91:1969;7012-7023
21. Brown H.C., Ravindran N. Synthesis. 1973;42-44
22. Block E., Corey E.R., Penn R.E., Renken T.L., Sherwin P.F. J. Am. Chem. Soc. 98:1976;5715-5717
23. Kabalka G.W., Baker J.D., Neal G.W. J. Org. Chem. 42:1977;512-517
24. Brown H.C., Weissman P.M., Yoon N.M. J. Am. Chem. Soc. 88:1966;1458-1463
25. Yoon N.M., Gyoung Y.S. J. Org. Chem. 50:1985;2443-2450
26. Ho T.L., Wong C.M. Org. Prep. Proced. Int. 7:1975;163-164
27. Ho T.L., Wong C.M. Synth. Commun. 3:1973;37-38
28. Akita Y., Inaba M., Uchida H., Ohta A. Synthesis. 1977;792-794
29. Olah G.A., Surya Prakash G.K., Ho T.L. Synthesis. 1976;810-811
30. Karimi B., Zareyee D. Synthesis. 2003;335-336
31. Yoo B.W., Choi K.H., Kim D.Y., Choi K.I., Kim J.H. Synth. Commun. 33:2003;53-57
32. Ishii A., Yamashita R., Saito M., Nakayama J. J. Org. Chem. 68:2003;1555-1558
33. This data will be presented elsewhere
34. Mancuso A.J., Swern D. Synthesis. 1981;165-185
35. Tidwell T.T. Org. React. 39:1990;297-303
36. Tidwell T.T. Synthesis. 1990;857-870
37. 3) spectra after work-up
38. 1H NMR spectrum). Purification by silica gel chromatography [hexane-propan-2-ol (100:1)] afforded 2 (343 mg, 75%) identical with a commercially available material