Palladium-catalyzed intermolecular α-arylation of N-protected 2-piperidinones

Organic Letters

Volumn 5, Issue 17, 2003, Pages 3037-3039

  Cossy, Janine ^a   de Filippis, Arnault ^a   Gomez Pardo, Domingo ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; PALLADIUM; PIPERIDONE DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL STRUCTURE;

EID: 0141743758     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0350036     Document Type: Article

References (30)

1. (a) Bunnett, J. F.; Zahler, R. E. Chem. Rev. 1952, 49, 273-412.
2. (b) Bunnett, J. F. Acc. Chem. Res. 1972, 5, 139-147.
3. (c) Paradisi, C. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 2.1 and references therein.
4. (d) Norris, R. K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 2.2 and references therein.
5. (e) Kessar, S. V. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 2.3 and references therein.
6. (a) Scolastico, C.; Poli, G. Chemtracts 1999, 12, 498-507.
7. (b) Bolm, C.; Hildebrand, J. P.; Muniz, K.; Hermanns, N. Angew. Chem., Int. Ed. 2001, 40, 3284-3308.
8. (c) Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041-2075.
9. (d) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
10. (e) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234-245.
11. (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109.
12. (b) Blake, C. H.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 9, 12382-12383.
13. (c) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370 and references therein.
14. (d) Solé, D.; Vallverdu, L.; Bonjoch, J. Adv. Synth. Catal. 2001, 343, 439-442.
15. (e) Solé, D.; Vallverdu, L.; Peidro, E.; Bonjoch, J. Chem. Commun. 2001, 1888-1889.
16. (f) Mutter, R.; Campbell, I. B.; Martin de la Nava, E. M.; Merritt, A. T.; Wills, M. J. Org. Chem. 2001, 56, 3284-3290.
17. (g) Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 5816-5817.
18. (h) Ehrentraut, A.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2002, 344, 209-217.
19. (i) Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261-1268.
20. (j) Viciu, M. S.; Kelly, R. A., III; Stevens, E. D.; Naud, F.; Studer, M.; Nolan, S. P. Org. Lett. 2003, 5, 1479-1482 and references therein.
21. (a) Moradi, W. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7996-8002.
22. (b) Lee, S.; Beare, N. A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 8410-8411.
23. (c) Jorgensen, M.; Lee, S.; Liu, X.; Wolkowski, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 12557-12565 and references therein.
24. (a) Shaughnessy, K. H.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1998, 63, 6546-6553.
25. (b) Freund, R.; Mederski, W. W. K. R. Helv. Chim. Acta 2000, 83, 1247-1255.
26. (c) Honda, T.; Namiki, H.; Satoh, F. Org. Lett. 2001, 3, 631-633.
27. (d) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402-3415.
28. (e) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 193-195.
29. 2. See: Spielvogel, D. J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 3500-3501.
30. 4, filtered, and concentrated under reduced pressure. The residue was then purified by chromatography on silica gel using 80/20 or 70/30 cyclohexane/ethyl acetate.