A mild, convenient synthesis of sulfinic acid salts and sulfonamides from alkyl and aryl halides

Tetrahedron Letters

Volumn 43, Issue 47, 2002, Pages 8479-8483

  Baskin, Jeremy M ^a   Wang, Zhaoyin ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

HALIDE; HETEROCYCLIC COMPOUND; ORGANOLITHIUM COMPOUND; REAGENT; SODIUM 3 METHOXY 3 OXOPROPANE 1 SULFINATE; SODIUM DERIVATIVE; SULFINIC ACID DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG SYNTHESIS; METHODOLOGY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

EID: 0037131711     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02073-7     Document Type: Article

References (21)

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9. For preparation of sulfinic acids and their derivatives see: (a) Org. Chem. Sulfur; Oae, S., Ed.; Plenum Press: New York, 1977; pp. 603-647; (b) Compr. Org. Chem.; Jones, D. N., Ed.; Pergamon Press: Oxford, 1979; Vol. 3, pp. 317-329; © Pinnick, H. W.; Reynolds, M. A. J. Org. Chem. 1979, 44, 160; (d) Huang, H.-C.; Reinhard, E. J.; Reitz, D. B. Tetrahedron Lett. 1994, 35, 7201-7204; (e) De Vleeschauwer, M.; Gauthier, J. Y. Synlett 1996, 375-377; (f) Sato, R.; Akutsu, Y.; Goto, T.; Saito M. Chem. Lett. 1987, 2161-2162; (g) Ueno, Y.; Kojima, A.; Okawara, M. Chem. Lett. 1984, 2125-2128.
10. For preparation of sulfinic acids and their derivatives see: (a) Org. Chem. Sulfur; Oae, S., Ed.; Plenum Press: New York, 1977; pp. 603-647; (b) Compr. Org. Chem.; Jones, D. N., Ed.; Pergamon Press: Oxford, 1979; Vol. 3, pp. 317-329; © Pinnick, H. W.; Reynolds, M. A. J. Org. Chem. 1979, 44, 160; (d) Huang, H.-C.; Reinhard, E. J.; Reitz, D. B. Tetrahedron Lett. 1994, 35, 7201-7204; (e) De Vleeschauwer, M.; Gauthier, J. Y. Synlett 1996, 375-377; (f) Sato, R.; Akutsu, Y.; Goto, T.; Saito M. Chem. Lett. 1987, 2161-2162; (g) Ueno, Y.; Kojima, A.; Okawara, M. Chem. Lett. 1984, 2125-2128.
11. For preparation of sulfinic acids and their derivatives see: (a) Org. Chem. Sulfur; Oae, S., Ed.; Plenum Press: New York, 1977; pp. 603-647; (b) Compr. Org. Chem.; Jones, D. N., Ed.; Pergamon Press: Oxford, 1979; Vol. 3, pp. 317-329; © Pinnick, H. W.; Reynolds, M. A. J. Org. Chem. 1979, 44, 160; (d) Huang, H.-C.; Reinhard, E. J.; Reitz, D. B. Tetrahedron Lett. 1994, 35, 7201-7204; (e) De Vleeschauwer, M.; Gauthier, J. Y. Synlett 1996, 375-377; (f) Sato, R.; Akutsu, Y.; Goto, T.; Saito M. Chem. Lett. 1987, 2161-2162; (g) Ueno, Y.; Kojima, A.; Okawara, M. Chem. Lett. 1984, 2125-2128.
12. For preparation of sulfinic acids and their derivatives see: (a) Org. Chem. Sulfur; Oae, S., Ed.; Plenum Press: New York, 1977; pp. 603-647; (b) Compr. Org. Chem.; Jones, D. N., Ed.; Pergamon Press: Oxford, 1979; Vol. 3, pp. 317-329; © Pinnick, H. W.; Reynolds, M. A. J. Org. Chem. 1979, 44, 160; (d) Huang, H.-C.; Reinhard, E. J.; Reitz, D. B. Tetrahedron Lett. 1994, 35, 7201-7204; (e) De Vleeschauwer, M.; Gauthier, J. Y. Synlett 1996, 375-377; (f) Sato, R.; Akutsu, Y.; Goto, T.; Saito M. Chem. Lett. 1987, 2161-2162; (g) Ueno, Y.; Kojima, A.; Okawara, M. Chem. Lett. 1984, 2125-2128.
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19. In the cases of benzyl chlorides, secondary benzyl bromides, and primary non-benzyl bromides, the reaction time was longer, up to 24 h.
20. 13C NMR and MS.
21. In the case of aryl bromides, 5 equiv. of CuI and of SMOPS were used instead of 3 equiv.