Copper(I)-promoted palladium-catalyzed cross-coupling of unsaturated tri-n-butylstannane with heteroaromatic thioether

Organic Letters

Volumn 5, Issue 6, 2003, Pages 803-805

  Alphonse, France Aimée ^a,b   Suzenet, Franck ^a   Keromnes, Anne ^b   Lebret, Bruno ^b   Guillaumet, Gérald ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b CEA LE RIPAULT   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; BROMINE DERIVATIVE; COPPER DERIVATIVE; METHYL GROUP; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFIDE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; ELECTRON;

EID: 0141563442     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027453o     Document Type: Article

References (33)

1. For reviews, see: (a) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985. (b) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley & Sons: New York, 1995. (c) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (e) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211. (f) Angiolelli, M. E.; Casalnuovo, A. L.; Selby, T. P. Synlett 2000, 6, 905-907.
2. For reviews, see: (a) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985. (b) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley & Sons: New York, 1995. (c) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (e) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211. (f) Angiolelli, M. E.; Casalnuovo, A. L.; Selby, T. P. Synlett 2000, 6, 905-907.
3. For reviews, see: (a) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985. (b) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley & Sons: New York, 1995. (c) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (e) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211. (f) Angiolelli, M. E.; Casalnuovo, A. L.; Selby, T. P. Synlett 2000, 6, 905-907.
4. For reviews, see: (a) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985. (b) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley & Sons: New York, 1995. (c) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (e) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211. (f) Angiolelli, M. E.; Casalnuovo, A. L.; Selby, T. P. Synlett 2000, 6, 905-907.
5. For reviews, see: (a) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985. (b) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley & Sons: New York, 1995. (c) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (e) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211. (f) Angiolelli, M. E.; Casalnuovo, A. L.; Selby, T. P. Synlett 2000, 6, 905-907.
6. For reviews, see: (a) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985. (b) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley & Sons: New York, 1995. (c) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (e) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211. (f) Angiolelli, M. E.; Casalnuovo, A. L.; Selby, T. P. Synlett 2000, 6, 905-907.
7. (a) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalysed Organic Reactions; Academic Press: London, 1997.
8. (b) Srogl, J.; Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1997, 119, 12376-12377.
9. (c) Srogl, J.; Liu, W.; Marshall, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1999, 121, 9449-9450.
10. (d) Darses, S.; Genêt, J.-P.; Brayer, J.-L.; Demoute, J.-P. Tetrahedron Lett. 1997, 38, 4393-4396.
11. (e) Kikukawa, K.; Kono, K.; Wada, F.; Matsuda, T. J. Org. Chem. 1983, 48, 1333-1336.
12. (f) Pridgen, L. N. J. Org. Chem. 1981, 46, 5402-5404.
13. (a) Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260-11261.
14. (b) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3, 91-93.
15. (c) Savarin, C.; Liebeskind, L. S. Org. Lett. 2001, 3, 2149-2152.
16. (d) Kusturin, C. L.; Liebeskind, L. S.; Neumann, W. L. Org. Lett. 2002, 4, 983-985.
17. (a) Alphonse, F.-A.; Suzenet, F.; Keromnes, A.; Lebret, B.; Guillaumet, G. Synlett 2002, 3, 447-450.
18. (b) Liebeskind, L. S.; Srogl, J. Org. Lett. 2002, 4, 979-981.
19. (a) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworth: London, 1987.
20. (b) Lee, A. S.-Y.; Dai, W.-C. Tetrahedron 1997, 53, 859-868 and references therein.
21. (c) Smith, N. D.; Mancuso, J.; Lautens, M. Chem. Rev. 2000, 100, 3257-3282.
22. Paudler, W. W.; Chem, I. K. J. Heterocycl. Chem. 1970, 7, 767-771.
23. Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119-122.
24. Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978-8985 and references therein.
25. Blank reaction performed without palladium catalyst gave no coupled compound, and starting material was mainly recovered, suggesting that palladium is essential in the coupling process.
26. (a) Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359-5364.
27. (b) Farina, V.; Kapadia, S. Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905-5911.
28. (c) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749.
29. (d) Falck, J. R.; Bhatt, R. K.; Ye, J. J. Am. Chem. Soc. 1995, 117, 5973-5982.
30. (a) Piers, E.; Yee, J. G. K.; Gladstone, P. L. Org. Lett. 2000, 2, 481-484.
31. (b) Piers, E.; McEachern, E. J.; Romero, M. A. J. Org. Chem. 1997, 62, 6034-6040.
32. (c) Piers, E.; Romero, M. A. J. Am. Chem. Soc. 1996, 118, 1215-1216.
33. (d) Piers, E.; Wong, T. J. Org. Chem. 1993, 58, 3609-3610.