Oxidation of aromatic and aliphatic triisopropylsilanylsulfanyls to sulfonyl chlorides: Preparation of sulfonamides

Tetrahedron Letters

Volumn 44, Issue 42, 2003, Pages 7821-7824

  Gareau, Yves ^a   Pellicelli, Jonathan ^a   Laliberté, Sébastien ^a   Gauvreau, Danny ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC COMPOUND; ALKYL GROUP; AROMATIC COMPOUND; CHLORINE DERIVATIVE; POTASSIUM NITRATE; SULFONAMIDE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; OXIDATION;

EID: 0141794003     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.073     Document Type: Article

References (19)

1. MacNeil S.L., Familoni O.B., Snieckus V. J. Org. Chem. 66:2001;3662.
2. Shafer S.J., Closson W.D. J. Org. Chem. 40:1975;889.
3. Percec V., Bera T.K., De B.B., Sanai Y., Smith J., Holerca M.N., Barboiu B., Grubbs R.B., Fréchet J.M.J. J. Org. Chem. 66:2001;2104-2117.
4. Rotella D.P., Sun Z., Zhu Y., Krupinski J., Pongrac R., Seliger L., Normandin D., Macor J.E. J. Med. Chem. 43:2000;5037-5043.
5. Kim D.-W., Ko Y.K., Kim S.H. Synthesis. 12:1992;1203-1204.
6. De Vleeschauwer M., Gauthier J.-Y. Synlett. 4:1997;375-377.
7. Shih T.L., Candelore M.R., Cascieri M.A., Chiu S.H.L., Colwell L.F. Jr., Deng L., Feeney W.P., Forrest M.J., Hom G.J., MacIntyre D.E., Miller R.R., Stearns R.A., Strader C.D., Tota L., Wyvratt M.J., Fisher M.H., Weber A.E. Bioorg. Med. Chem. Lett. 9:1999;1251-1254.
8. Elslager E.F., Colbry N.L., Davoll J., Hutt M.P., Johnson J.L., Werbel L.M. J. Med. Chem. 27:1984;1740-1743.
9. Hoffman R.V. Org. Synth. 60:1981;121-126.
10. Lube A., Neumann W.P., Niestroj M. Chem. Ber. 128:1995;1195-1198.
11. Corrie J.E.T., Papageorgiou G. J. Chem. Soc., Perkin Trans. 1. 13:1996;1583-1592.
12. Tamura Y., Watanabe F., Nakatani T., Yasui K., Fuji M., Komurasaki T., Tsuzuki H., Maekawa R., Yoshioka T., Kawada K., Sugita K., Ohtani M. J. Med. Chem. 41:1998;640-649.
13. Mathieu-Pelta I., Evans S.A. J. Org. Chem. 57:1992;3409-3413.
14. Harpp D.N., Friedlander B.T., Larsen C., Steliou K., Stockton A. J. Org. Chem. 43:1978;3481-3485.
15. Rane A.M., Miranda E.I., Soderquist J.A. Tetrahedron Lett. 35:1994;3225-3226.
16. Arnould J.C., Didelot M., Cadilhac C., Pasquet M.J. Tetrahedron Lett. 37:1996;4523-4524.
17. Park Y.J., Shin H.H., Kim Y.H. Chem Lett. 1992;1483-1486.
18. With diethyl amine, a 65% yield of sulfonamide was obtained when the oxidation was run at -78°C and 76% yield with the addition of Hünig's base.
19. 13C NMR and either by elemental analysis or HRMS. Melting point was obtained on solid compounds. Once pure, the trialkylsilanylsulfanyls are reasonably air-stable and only have a slight odor if any. They are usually kept at 0°C for many weeks.