The first Negishi cross-coupling reaction of two alkyl centers utilizing a Pd-N-heterocyclic carbene (NHC) catalyst

Organic Letters

Volumn 7, Issue 17, 2005, Pages 3805-3807

  Hadei, Niloufar ^a   Kantchev, Eric Assen B ^a   O'Brien, Christopher J ^a   Organ, Michael G ^a  

^a YORK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 24044441578     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0514909     Document Type: Article

References (39)

1. (a) Metal-Catalyzed Cross-Coupling Reactions, 2 ed.; de Meijere, A., Diederich, F., Eds.; John Wiley & Sons: New York, 2004.
2. (b) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley & Sons: New York, 2002.
3. (a) Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674-688.
4. (b) Cárdenas, D. J. Angew. Chem., Int. Ed. 2003, 42, 384-387.
5. (a) Kochi, J. K. J. Organomet. Chem. 2002, 653, 11-19.
6. (b) Castle, P. L.; Widdowson, D. A. Tetrahedron Lett. 1986, 27, 6013-6016.
7. (c) Nunomoto, S.; Kawakami, Y.; Yamashita, J. J. Org. Chem. 1983, 48, 1912-1914.
8. (d) Tamura, M.; Kochi, J. K. J. Organomet. Chem. 1972, 42, 205-228.
9. (e) Tamura, M.; Kochi, J. J. Organomet. Chem. 1971, 31, 289-309.
10. (f) Tamura, M.; Kochi, J. Synthesis 1971, 303-305.
11. (g) Kochi, J. K.; Tamura, M. J. Am. Chem. Soc. 1971, 93, 1485-1487.
12. (h) Kochi, J. K.; Tamura, M. J. Am. Chem. Soc. 1971, 93, 1483-1485.
13. Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 12527-12530.
14. (a) Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 13662-13663.
15. (b) Kirchhoff, J. H.; Dai, C.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 1945-1947.
16. (c) Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 3910-3912.
17. (d) Netherton, M. R.; Dai, C.; Neuschütz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099-10100.
18. (a) Terao, J.; Todo, H.; Watanabe, H.; Ikumi, A.; Kambe, N. Angew. Chem., Int. Ed. 2004, 43, 6180-6182.
19. (b) Terao, J.; Nii, S.; Chowdhury, F. A.; Nakamura, A.; Kambe, N. Adv. Synth. Catal. 2004, 346, 905-908.
20. (c) Terao, J.; Naitoh, Y.; Kuniyasu, H.; Kambe, N. Chem. Lett. 2003, 32, 890-891.
21. (a) Fischer, C.; Fu, G. C. J. Am. Chem. Soc. 2005, 126, 4594-4595.
22. (b) Anderson, T. J.; Jones, G. D.; Vicic, D. A. J. Am. Chem. Soc. 2004, 126, 8100-8101.
23. (c) Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. 2004, 346, 1525-1532.
24. (d) Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 14726-14727.
25. (e) Terao, J.; Watanabe, H.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2002, 123, 4222-4223.
26. (f) Jensen, A. E.; Knochel, P. J. Org. Chem. 2002, 67, 79-85.
27. (g) Giovanini, R.; Stüdermann, T.; Devasagayaraj, A.; Dussin, G.; Knochel, P. J. Org. Chem. 1999, 64, 3544-3553.
28. (h) Giovanini, R.; Stüdermann, T.; Dussin, G.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 2387-2390.
29. Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686-3687.
30. Hills, I. D.; Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5749-5752.
31. Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Org. Lett. 2005, 7, 1991-1994.
32. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
33. (a) Arentsen, K.; Caddick, S.; Cloke, F. G. N.; Herring, A. P.; Hitchcock, P. B. Tetrahedron Lett. 2004, 45, 3511-3515.
34. NHC ligands have also been employed in Sonogashira and Kumada reactions of alkyl bromides; see: (b) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642-13643.
35. (c) Frisch, A. C.; Rataboul, F.; Zapf, A.; Beller, M. J. Organomet. Chem. 2003, 687, 403-409.
36. 2. See: Rieke, R. D.; Hanson, M. V.; Brown, J. D.; Niu, Q. J. J. Org. Chem. 1996, 61, 2726-2730.
37. Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445-1453. We believe this is due to the bromide ion from LiBr (produced as a byproduct in Rieke zinc fromation) displacing the tosylate group (GC/MS). Indeed, when we used commercially available organozinc reagent (Rieke Metals, Inc., which contains LiCl), we observed significant formation of the alkyl chloride (GC/ MS).
38. Steric nature of the organozinc reagent could affect the formation of the active catalyst. We observed significant variation in yield when the organozinc reagent participating in the cross-coupling reaction was used alone.
39. Reaction depicted in Table 3, entry 4, yielded 87% of the cross-coupled product when n-butylzinc bromide catalyst activation was not employed.