η2-dba complexes of Pd(0): The substituent effect in Suzuki-Miyaura coupling

Organic Letters

Volumn 6, Issue 24, 2004, Pages 4435-4438

  Fairlamb, Ian J S ^a   Kapdi, Anant R ^a   Lee, Adam F ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUP; LIGAND; NITROGEN DIOXIDE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; COMPLEX FORMATION; CROSS COUPLING REACTION; ELECTRON; ELECTRON TRANSPORT; ELECTRONICS; SUBSTITUTION REACTION; SUZUKI MIYAURA COUPLING; SUZUKI REACTION;

EID: 10144222904     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048413i     Document Type: Article

References (31)

1. (a) Heck, R. F. In Palladium Reagents in Organic Syntheses; Academic Press: New York, 1985.
2. (b) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley & Sons: Hoboken, NJ, 2002.
3. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
4. (a) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; VCH: Weinheim, 1998; p 49.
5. (b) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 37, 3387.
6. (c) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
7. (d) Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413.
8. (e) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804.
9. (f) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153.
10. (g) Andreu, M. G.; Zapf, A.; Beller, M. Chem. Commun. 2000, 2475.
11. (h) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
12. (i) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677.
13. (j) Li, G. Y. J. Org. Chem. 2002, 67, 3643.
14. (k) Bedford, R. B.; Cazin, C. S. J.; Coles, S. J.; Gelbrich, T.; Horton, P. N.; Hursthouse, M. B.; Light, M. E. Organometallics 2003, 22, 987.
15. (l) Navarro, O.; Kelly, R. A., III; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194.
16. Amatore, C.; Jutand, A. Coordin. Chem. Rev. 1998, 178-180, 511 and references therein.
17. (a) Amatore, C.; Jutand, A.; Khalil, F.; M'Barki, M. A.; Mottier, L. Organometallics 1993, 12, 3168.
18. (b) Amatore, C.; Broeker, G.; Jutand, A.; Khalil, F. J. Am. Chem. Soc. 1997, 119, 5176.
19. (c) Amatore, C.; Jutand, A.; Meyer, G. Inorg. Chim. Acta 1998, 273, 76.
20. The π-donor properties of the dba ligand are not expected to play a decisive role when strongly σ-donating ligands are employed. They could become important using more π-accepting phosphine ligands.
21. Takahashi, Y.; Ito, T.; Sakai, S.; Ishii, Y. J. Chem. Soc., Dalton Trans. 1970, 1065.
22. Complexes 2e and 2f were isolated as hydrate complexes.
23. Arentsen, K.; Caddick, S.; Cloke, F. G. N.; Herring, A. P.; Hitchcock, P. B. Tetrahedron Lett. 2004, 45, 3511.
24. The phrase "ligand-free" is used when no additional ligand, such as a phosphine, is added to the reaction; see: de Vries, A. H. M.; Mulders, J. M. C. A.; Mommers, J. H. M.; Henderickx, H. J. W.; de Vries, J. G. Org. Lett. 2003, 5, 3285.
25. We have employed this substrate for several cross-coupling processes; see: (a) Marrison, L. R.; Dickinson, J. M.; Fairlamb, I. J. S. Bioorg. Med. Chem. Lett. 2002, 12, 3509. (b) Marrison, L. R.; Dickinson, J. M.; Ahmed, R.; Fairlamb, I. J. S. Tetrahedron Lett. 2002, 43, 8853. (c) Marrison, L. R.; Dickinson, J. M.; Ahmed, R.; Fairlamb, I. J. S. Bioorg. Med. Chem. Lett. 2003, 13, 2667. (d) Fairlamb, I. J. S.; Lu, F.-J.; Schmidt, J.-P. Synthesis 2003, 2564. (e) Fairlamb, I. J. S.; Bäuerlein, P. S.; Marrison, L. R.; Dickinson, J. M. Chem. Commun. 2003, 632. (f) Niemela, E. H.; Lee, A. F.; Fairlamb, I. J. S. Tetrahedron Lett. 2004, 45, 3593. (g) Fairlamb, I. J. S.; Marrison, L. R.; Dickinson, J. M.; Lu, F.-J.; Schmidt, J.-P. Bioorg. Med. Chem. 2004, 12, 4285.
26. We have employed this substrate for several cross-coupling processes; see: (a) Marrison, L. R.; Dickinson, J. M.; Fairlamb, I. J. S. Bioorg. Med. Chem. Lett. 2002, 12, 3509. (b) Marrison, L. R.; Dickinson, J. M.; Ahmed, R.; Fairlamb, I. J. S. Tetrahedron Lett. 2002, 43, 8853. (c) Marrison, L. R.; Dickinson, J. M.; Ahmed, R.; Fairlamb, I. J. S. Bioorg. Med. Chem. Lett. 2003, 13, 2667. (d) Fairlamb, I. J. S.; Lu, F.-J.; Schmidt, J.-P. Synthesis 2003, 2564. (e) Fairlamb, I. J. S.; Bäuerlein, P. S.; Marrison, L. R.; Dickinson, J. M. Chem. Commun. 2003, 632. (f) Niemela, E. H.; Lee, A. F.; Fairlamb, I. J. S. Tetrahedron Lett. 2004, 45, 3593. (g) Fairlamb, I. J. S.; Marrison, L. R.; Dickinson, J. M.; Lu, F.-J.; Schmidt, J.-P. Bioorg. Med. Chem. 2004, 12, 4285.
27. We have employed this substrate for several cross-coupling processes; see: (a) Marrison, L. R.; Dickinson, J. M.; Fairlamb, I. J. S. Bioorg. Med. Chem. Lett. 2002, 12, 3509. (b) Marrison, L. R.; Dickinson, J. M.; Ahmed, R.; Fairlamb, I. J. S. Tetrahedron Lett. 2002, 43, 8853. (c) Marrison, L. R.; Dickinson, J. M.; Ahmed, R.; Fairlamb, I. J. S. Bioorg. Med. Chem. Lett. 2003, 13, 2667. (d) Fairlamb, I. J. S.; Lu, F.-J.; Schmidt, J.-P. Synthesis 2003, 2564. (e) Fairlamb, I. J. S.; Bäuerlein, P. S.; Marrison, L. R.; Dickinson, J. M. Chem. Commun. 2003, 632. (f) Niemela, E. H.; Lee, A. F.; Fairlamb, I. J. S. Tetrahedron Lett. 2004, 45, 3593. (g) Fairlamb, I. J. S.; Marrison, L. R.; Dickinson, J. M.; Lu, F.-J.; Schmidt, J.-P. Bioorg. Med. Chem. 2004, 12, 4285.
28. We have employed this substrate for several cross-coupling processes; see: (a) Marrison, L. R.; Dickinson, J. M.; Fairlamb, I. J. S. Bioorg. Med. Chem. Lett. 2002, 12, 3509. (b) Marrison, L. R.; Dickinson, J. M.; Ahmed, R.; Fairlamb, I. J. S. Tetrahedron Lett. 2002, 43, 8853. (c) Marrison, L. R.; Dickinson, J. M.; Ahmed, R.; Fairlamb, I. J. S. Bioorg. Med. Chem. Lett. 2003, 13, 2667. (d) Fairlamb, I. J. S.; Lu, F.-J.; Schmidt, J.-P. Synthesis 2003, 2564. (e) Fairlamb, I. J. S.; Bäuerlein, P. S.; Marrison, L. R.; Dickinson, J. M. Chem. Commun. 2003, 632. (f) Niemela, E. H.; Lee, A. F.; Fairlamb, I. J. S. Tetrahedron Lett. 2004, 45, 3593. (g) Fairlamb, I. J. S.; Marrison, L. R.; Dickinson, J. M.; Lu, F.-J.; Schmidt, J.-P. Bioorg. Med. Chem. 2004, 12, 4285.
29. We have employed this substrate for several cross-coupling processes; see: (a) Marrison, L. R.; Dickinson, J. M.; Fairlamb, I. J. S. Bioorg. Med. Chem. Lett. 2002, 12, 3509. (b) Marrison, L. R.; Dickinson, J. M.; Ahmed, R.; Fairlamb, I. J. S. Tetrahedron Lett. 2002, 43, 8853. (c) Marrison, L. R.; Dickinson, J. M.; Ahmed, R.; Fairlamb, I. J. S. Bioorg. Med. Chem. Lett. 2003, 13, 2667. (d) Fairlamb, I. J. S.; Lu, F.-J.; Schmidt, J.-P. Synthesis 2003, 2564. (e) Fairlamb, I. J. S.; Bäuerlein, P. S.; Marrison, L. R.; Dickinson, J. M. Chem. Commun. 2003, 632. (f) Niemela, E. H.; Lee, A. F.; Fairlamb, I. J. S. Tetrahedron Lett. 2004, 45, 3593. (g) Fairlamb, I. J. S.; Marrison, L. R.; Dickinson, J. M.; Lu, F.-J.; Schmidt, J.-P. Bioorg. Med. Chem. 2004, 12, 4285.
30. We have employed this substrate for several cross-coupling processes; see: (a) Marrison, L. R.; Dickinson, J. M.; Fairlamb, I. J. S. Bioorg. Med. Chem. Lett. 2002, 12, 3509. (b) Marrison, L. R.; Dickinson, J. M.; Ahmed, R.; Fairlamb, I. J. S. Tetrahedron Lett. 2002, 43, 8853. (c) Marrison, L. R.; Dickinson, J. M.; Ahmed, R.; Fairlamb, I. J. S. Bioorg. Med. Chem. Lett. 2003, 13, 2667. (d) Fairlamb, I. J. S.; Lu, F.-J.; Schmidt, J.-P. Synthesis 2003, 2564. (e) Fairlamb, I. J. S.; Bäuerlein, P. S.; Marrison, L. R.; Dickinson, J. M. Chem. Commun. 2003, 632. (f) Niemela, E. H.; Lee, A. F.; Fairlamb, I. J. S. Tetrahedron Lett. 2004, 45, 3593. (g) Fairlamb, I. J. S.; Marrison, L. R.; Dickinson, J. M.; Lu, F.-J.; Schmidt, J.-P. Bioorg. Med. Chem. 2004, 12, 4285.
31. We have employed this substrate for several cross-coupling processes; see: (a) Marrison, L. R.; Dickinson, J. M.; Fairlamb, I. J. S. Bioorg. Med. Chem. Lett. 2002, 12, 3509. (b) Marrison, L. R.; Dickinson, J. M.; Ahmed, R.; Fairlamb, I. J. S. Tetrahedron Lett. 2002, 43, 8853. (c) Marrison, L. R.; Dickinson, J. M.; Ahmed, R.; Fairlamb, I. J. S. Bioorg. Med. Chem. Lett. 2003, 13, 2667. (d) Fairlamb, I. J. S.; Lu, F.-J.; Schmidt, J.-P. Synthesis 2003, 2564. (e) Fairlamb, I. J. S.; Bäuerlein, P. S.; Marrison, L. R.; Dickinson, J. M. Chem. Commun. 2003, 632. (f) Niemela, E. H.; Lee, A. F.; Fairlamb, I. J. S. Tetrahedron Lett. 2004, 45, 3593. (g) Fairlamb, I. J. S.; Marrison, L. R.; Dickinson, J. M.; Lu, F.-J.; Schmidt, J.-P. Bioorg. Med. Chem. 2004, 12, 4285.