Palladium-catalyzed N-vinylation of sulfoximines

Journal of Organic Chemistry

Volumn 69, Issue 24, 2004, Pages 8518-8520

  Dehli, Juan R ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; BROMINE COMPOUNDS; CATALYSIS; HYDROGENATION; PALLADIUM; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

COUPLING REACTIONS; N-VINYL SULFOXIMINES; SULFOXIMINES; VINYL MOIETY;

MOLECULAR DYNAMICS;

BROMIDE; IMINE; PALLADIUM; SULFOXIMINE DERIVATIVE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; HYDROGENATION; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS; VINYLATION;

BROMIDES; CATALYSIS; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM; SULFONAMIDES; VINYL COMPOUNDS;

EID: 9344223991     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0485583     Document Type: Article

References (37)

1. (a) Okamura, H.; Bolm, C. Chem. Lett. 2004, 33, 482-487.
2. (b) Harmata, M. Chemtracts-Org. Chem. 2003, 16, 660-666.
3. For a recent review on sulfoximines, see: Reggelin, M.; Zur, C. Synthesis 2000, 1-64.
4. (a) Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, Germany, 2000.
5. (b) Comprehensive Asymmetric Catalysis, Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, Germany, 1999.
6. (c) Transitions Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
7. (d) Bolm, C., Gladysz, J., Eds. Chem. Rev. 2003, 103, 2761-3400.
8. (a) Bolm, C.; Hildebrand, J. P. J. Org. Chem. 2000, 65, 169-175.
9. (b) Bolm, C.; Hildebrand, J. P. Tetrahedron Lett. 1998, 39, 5731-5734.
10. (c) Bolm, C.; Martin, M.; Gibson, L. Synlett 2002, 832-834.
11. (d) Harmata, M.; Hong, X.; Ghosh, S. K. Tetrahedron Lett. 2004, 45, 5233-5236.
12. (e) For a related intramolecular α-arylation of sulfoximines, see: Bolm, C.; Okamura, H.; Verrucci, M. J. Organomet. Chem. 2003, 687, 444-450.
13. (f) For a recently reported Cu-promoted N-arylation, see: Cho, G.-Y.; Rémy, P.; Jansson, J.; Moessner, C.; Bolm, C. Org. Lett. 2004, 6, 3293-3296. Due to its aqueous and acidic workup, this methodology was expected to be incompatible with the water and acid sensitivity of the vinyl sulfoximines prepared here.
14. Bolm, C.; Hildebrand, J. P.; Rudolph, J. Synthesis 2000, 911-913.
15. (a) Bolm, C.; Martin, M.; Simic, O.; Verrucci, M. Org. Lett. 2003, 5, 427-429.
16. (b) Bolm, C.; Martin, M.; Gescheidt, G.; Palivan, C.; Neshchadin, D.; Bertagnolli, H.; Feth, M.; Schweiger, A.; Mitrikas, G.; Harmer, J. J. Am. Chem. Soc. 2003, 125, 6222-6227.
17. (a) Bolm, C.; Verrucci, M.; Simic, O.; Cozzi, P. G.; Raabe, G.; Okamura, H. Chem. Commun. 2003, 2826-2827.
18. (b) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830-3831.
19. (a) Bolm, C.; Simic, O.; Martin, M. Synlett 2001, 1878-1880.
20. (b) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321-3323.
21. Langner, M.; Bolm, C. Angew. Chem., in press.
22. (a) Barluenga, J.; Fernández, M. A.; Aznar, F.; Valdés, C. Chem. Eur. J. 2004, 10, 494-507.
23. (b) Barluenga, J.; Fernández, M. A.; Aznar, F.; Valdés, C. Chem. Commun. 2002, 2362-2363.
24. (c) For a recent report on the use of vinyl chlorides as coupling partners, see: Barluenga, J.; Fernández, M. A.; Aznar, F.; Valdés, C. Chem. Commun. 2004, 1400-1401.
25. (a) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111-114.
26. (b) For the amidation of meso-brominated porphyrines, see: Gao, G.-Y.; Chen, Y.; Zhang, X. P. Org. Lett. 2004, 6, 1837-1840.
27. Lebedev, A. Y.; Izmer, V. V.; Kazyul'kin, D. N.; Beletskaya, I. P.; Voskoboynikov, A. Z. Org. Lett. 2002, 4, 623-626.
28. Barluenga, J.; Aznar, F.; Valdés, C. Angew. Chem., Int. Ed. 2004, 43, 343-345.
29. (a) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131-209.
30. (b) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, Germany, 2000; pp 195-262.
31. For reviews on the synthesis and general reactivity of vinyl triflates, see: (a) Ritter, K. Synthesis 1993, 735-762.
32. (b) Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85-124.
33. Willis, M. C.; Brace, G. N. Tetrahedron Lett. 2002, 43, 9085-9088.
34. Wallace, D. J.; Klauber, D. J.; Chen, C.; Volante, R. P. Org. Lett. 2003, 5, 4749-4752.
35. Bolm, C.; Hackenberger, C. P. R.; Simic, O.; Verrucci, M.; Müller, D.; Bienewald, F. Synthesis 2002, 879-887 and references therein.
36. During the course of our work, Katritzky reported on the N-alkylation of sulfoximines: Katritzky, A. R.; Zhang, Y.; Singh, S. K.; Le Gall, Y. P. Arkivoc 2003, xv, 115-123.
37. Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305-1307.