Palladium(0) Catalyzed Cross Coupling Reactions of Hindered, Double Activated Aryl Halides with Organozinc Reagents - The Effect of Copper(I) Cocatalysis

Synlett

Volumn 1996, Issue 5, 1996, Pages 473-474

  Weichert, Andreas ^a   Bauer, Martina ^a   Wirsig, Petra ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001114063     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5445     Document Type: Article

References (23)

1. For reviews see (a) Kumada, M. Pure Appl. Chem. 1980, 52, 669; (b) Negishi, E. Acc. Chem. Res. 1982, 15, 340. (c) Heck, R.F. "Palladium Reagents in Organic Syntheses", Academic Press, London, 1985; (d) Stille, J. K. Angew. Chem. 1986, 98, 504; (e) Mitchell, T. N. Synthesis 1992, 803.
2. For reviews see (a) Kumada, M. Pure Appl. Chem. 1980, 52, 669; (b) Negishi, E. Acc. Chem. Res. 1982, 15, 340. (c) Heck, R.F. "Palladium Reagents in Organic Syntheses", Academic Press, London, 1985; (d) Stille, J. K. Angew. Chem. 1986, 98, 504; (e) Mitchell, T. N. Synthesis 1992, 803.
3. For reviews see (a) Kumada, M. Pure Appl. Chem. 1980, 52, 669; (b) Negishi, E. Acc. Chem. Res. 1982, 15, 340. (c) Heck, R.F. "Palladium Reagents in Organic Syntheses", Academic Press, London, 1985; (d) Stille, J. K. Angew. Chem. 1986, 98, 504; (e) Mitchell, T. N. Synthesis 1992, 803.
4. For reviews see (a) Kumada, M. Pure Appl. Chem. 1980, 52, 669; (b) Negishi, E. Acc. Chem. Res. 1982, 15, 340. (c) Heck, R.F. "Palladium Reagents in Organic Syntheses", Academic Press, London, 1985; (d) Stille, J. K. Angew. Chem. 1986, 98, 504; (e) Mitchell, T. N. Synthesis 1992, 803.
5. For reviews see (a) Kumada, M. Pure Appl. Chem. 1980, 52, 669; (b) Negishi, E. Acc. Chem. Res. 1982, 15, 340. (c) Heck, R.F. "Palladium Reagents in Organic Syntheses", Academic Press, London, 1985; (d) Stille, J. K. Angew. Chem. 1986, 98, 504; (e) Mitchell, T. N. Synthesis 1992, 803.
6. (a) Majid, T. N.; Knochel, P. Tetrahedron Lett. 1990, 31, 4413;
7. (b) Labaudinière, L.; Normant, J.-F. Tetrahedron Lett. 1992, 33, 6139;
8. (c) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117;
9. (d) Takagi, K. Chem. Lett. 1993, 469;
10. (e) Fürstner, A.; Singer, R.; Knochel, P. Tetrahedron Lett. 1994, 35, 1047;
11. (f) Gao, Y.; Harada, K.; Hata, T.; Urabe, H.; Sato, F. J. Org. Chem. 1995, 60, 290.
12. Negishi pioneered the cross-coupling of organozincs with electrophiles, Negishi, E.; King, A. O.; Okukado, N. J. J. Org. Chem. 1977, 42, 1821.
13. Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374
14. a) Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158;
15. b) Hayashi, T.; Konishi, M.; Kumada, M. Tetrahedron Lett. 1979, 21, 1871.
16. Marino, J. P.; Long, J. K. J. Am. Chem. Soc. 1988, 110, 7916.
17. a) Liebeskind, L. S.; Wang, J. Tetrahedron Lett. 1990, 31, 4293;
18. b) Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359.
19. Farina, V.; Kapadia, S.; Krishan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905.
20. 3) d 8.70 (d, 1H, J= 2.5 Hz), 8.20 (dd, 1H, J= 2.5 / 8.5 Hz), 7.46 (d, 1H, J= 8.5 Hz), 3.94 (s, 3H), 3.10 (s, 3H), 2.98 (d, 2H, J= 7.5 Hz), 2.12 (sym m, 1H), 0.98 (d, 6H, J= 6 Hz).
21. 1H-NMR, MS) consistent with the depicted structures.
22. Yields relate to isolated products and are not optimized.
23. 2 in THF (0.5 N, 22.8 mmol, 45.6 ml). After stirring at reflux for 2h, this mixture was used as mentioned under ref. 9, employing conditions B (Table III).