Palladium-Catalyzed Stille Cross-Couplings of Sulfonyl Chlorides and Organostannanes

Journal of the American Chemical Society

Volumn 125, Issue 50, 2003, Pages 15292-15293

  Dubbaka, Srinivas Reddy ^a   Vogel, Pierre ^a  

^a EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLSULFONYLCHLORIDE; COPPER; ORGANOSTANNANE DERIVATIVE; ORGANOTIN COMPOUND; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFONE DERIVATIVE; SULFONYL CHLORIDE DERIVATIVE; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS LINKING; ELIMINATION REACTION; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS; TECHNIQUE; TEMPERATURE DEPENDENCE;

EID: 0347480554     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038328q     Document Type: Article

References (32)

1. (a) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985.
2. (b) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley & Sons: New York, 1995.
3. (c) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, Chapter 4.
4. For reviews of the Stille reaction, see (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
5. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J.; The Stille Reactions, Organic Reactions; Wiley & Sons: New York, 1997, Vol. 50, 1-652.
6. (c) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
7. (d) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469.
8. (a) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636-3638.
9. (b) Kosugi, M.; Sasazawa, K.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 301-302.
10. (c) Mitchell, T. N. Synthesis 1992, 803-815.
11. (a) Kasahara, A.; Izumi, T.; Kudou, N.; Hiroshi, A.; Yamamoto, S. Chem. Ind. (London) 1988, 51-52.
12. (b) Miura, M.; Hashimoto, H.; Itoh, K.; Nomura, M. Tetrahedron Lett. 1989, 30, 975-976.
13. (c) Miura, M.; Hashimoto, H.; Itoh, K.; Nomura, M. J. Chem. Soc., Perkin. Trans. 1 1990, 8, 2207-2211.
14. Miura, M.; Itoh, K.; Nomura, M. Chem. Lett. 1989, 77-78.
15. Miura, M.; Hashimoto, H.; Itoh, K.; Nomura, M. Chem. Lett. 1990, 459.
16. Oae, S.; Togo, H. Bull. Chem. Soc. Jpn. 1983, 56, 3802-3812.
17. 4), filtered, concentrated under reduced pressure (solvents were removed under reflux on cooling to -20 °C in the cases of low boiling point or low molecular mass compounds), and purified by flash chromatography.
18. Piers, E.; Wong, T. J. Org. Chem. 1993, 58, 3609-3610.
19. Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; Wiley-Interscience: New York, 1980.
20. Alphonse, F.-A.; Suzenet, F.; Keromnes, A.; Lebret, B.; Guillaumet, G. Org. Lett. 2003, 5, 803-805.
21. 3CN, see ref 5.
22. See Supporting Information for reaction from sulfonyl chloride to sulfenyl chloride.
23. (a) Holmquist, H. E.; Carnahan, J. E. J. Org. Chem. 1960, 25, 2240.
24. (b) Shim, S. C.; Antebi, S.; Alper, H. J. Org. Chem. 1985, 50, 147-149.
25. (c) Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 2609-2612.
26. Kunniyasu, H.; Ogawa, A.; Miyazaki, S.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 9796-9803.
27. Kawakami, J.-I.; Mihara, M.; Kamiya, I. Takeda, M.; Ogawa, A.; Sonoda, N. Tetrahedron 2003, 59, 3521-3526.
28. Berbriter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058-9064.
29. Aryl chlorides react only when using electron-rich or sterically hindered ligands. See, for example: (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411-2413.
30. (b) Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413-2416.
31. Aryl bromides are reactive under these conditions. See, for example: Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
32. For reaction work up, see Supporting Information.