New air-stable planar chiral ferrocenyl monophosphine ligands: Suzuki cross-coupling of aryl chlorides and bromides

Organic Letters

Volumn 5, Issue 17, 2003, Pages 3025-3028

  Jensen, Jakob F ^a   Johannsen, Mogens ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; BROMINE DERIVATIVE; CHLORINE DERIVATIVE; FERROCENYLMONOPHOSPHINE; LIGAND; PALLADIUM; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ELECTRON; ROOM TEMPERATURE;

EID: 0141743760     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034943n     Document Type: Article

References (35)

1. (a) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998.
2. (b) Farina, V. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 161.
3. (c) Tsuji, J. In Palladium Reagents and Catalyst; John Wiley and Sons: Chichester, UK, 1995.
4. (d) Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 8, p 799.
5. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
6. Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047.
7. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
8. The biaryl system is a well-established part of many superb ligands. For an illustrative example, see for example: Buchwald, S. L.; Old, D. W.; Wolfe, J. P.; Palucki, M.; Kamikawa, K. US 6307087 B1, October 23, 2001.
9. (a) Pedersen, H. L.; Johannsen, M. Chem. Commun. 1999, 2517.
10. (b) Pedersen, H. L.; Johannsen, M. J. Org. Chem. 2002, 67, 7982.
11. (c) Jensen, J. F.; Søtofte, I.; Sørensen, H. O.; Johannsen, M. J. Org. Chem. 2003, 68, 1258. For other reports on optically pure aryl-ferrocenyl complexes, see:
12. For other reports on optically pure aryl-ferrocenyl complexes, see: (d) Bringmann, G.; Hinrichs, J.; Peters, K.; Peters, E.-V. J. Org. Chem. 2001, 66, 629. (e) Lotz, M.; Kramer, G.; Knochel, P. Chem. Commun. 2002, 2546.
13. For other reports on optically pure aryl-ferrocenyl complexes, see: (d) Bringmann, G.; Hinrichs, J.; Peters, K.; Peters, E.-V. J. Org. Chem. 2001, 66, 629. (e) Lotz, M.; Kramer, G.; Knochel, P. Chem. Commun. 2002, 2546.
14. For the synthesis of optically pure (Sp,Ss)-l, see also ref 6c.
15. The ferrocene sulfoxide chemistry was originally developed by Kagan et al.: (a) Riant, O.; Samuel, O.; Flessner, T.; Taudien, S.; Kagan, H. B. J. Org. Chem. 1997, 62, 6733. (b) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511. See also: (c) Hua, D. H.; Lagneau, N. M.; Chen, Y.; Robben, P. M.; Clapham, G.; Robinson, P. D. J. Org. Chem. 1996, 61, 4508. For the azaferrocenyl series, see: (d) Hansen, J. G.; Søtofte, I.; Johannsen, M. Org. Lett. 2001, 3, 499. (e) Hansen. J. G.; Johannsen, M. J. Org. Chem. 2002, 68, 1266.
16. The ferrocene sulfoxide chemistry was originally developed by Kagan et al.: (a) Riant, O.; Samuel, O.; Flessner, T.; Taudien, S.; Kagan, H. B. J. Org. Chem. 1997, 62, 6733. (b) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511. See also: (c) Hua, D. H.; Lagneau, N. M.; Chen, Y.; Robben, P. M.; Clapham, G.; Robinson, P. D. J. Org. Chem. 1996, 61, 4508. For the azaferrocenyl series, see: (d) Hansen, J. G.; Søtofte, I.; Johannsen, M. Org. Lett. 2001, 3, 499. (e) Hansen. J. G.; Johannsen, M. J. Org. Chem. 2002, 68, 1266.
17. The ferrocene sulfoxide chemistry was originally developed by Kagan et al.: (a) Riant, O.; Samuel, O.; Flessner, T.; Taudien, S.; Kagan, H. B. J. Org. Chem. 1997, 62, 6733. (b) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511. See also: (c) Hua, D. H.; Lagneau, N. M.; Chen, Y.; Robben, P. M.; Clapham, G.; Robinson, P. D. J. Org. Chem. 1996, 61, 4508. For the azaferrocenyl series, see: (d) Hansen, J. G.; Søtofte, I.; Johannsen, M. Org. Lett. 2001, 3, 499. (e) Hansen. J. G.; Johannsen, M. J. Org. Chem. 2002, 68, 1266.
18. The ferrocene sulfoxide chemistry was originally developed by Kagan et al.: (a) Riant, O.; Samuel, O.; Flessner, T.; Taudien, S.; Kagan, H. B. J. Org. Chem. 1997, 62, 6733. (b) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511. See also: (c) Hua, D. H.; Lagneau, N. M.; Chen, Y.; Robben, P. M.; Clapham, G.; Robinson, P. D. J. Org. Chem. 1996, 61, 4508. For the azaferrocenyl series, see: (d) Hansen, J. G.; Søtofte, I.; Johannsen, M. Org. Lett. 2001, 3, 499. (e) Hansen. J. G.; Johannsen, M. J. Org. Chem. 2002, 68, 1266.
19. The ferrocene sulfoxide chemistry was originally developed by Kagan et al.: (a) Riant, O.; Samuel, O.; Flessner, T.; Taudien, S.; Kagan, H. B. J. Org. Chem. 1997, 62, 6733. (b) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511. See also: (c) Hua, D. H.; Lagneau, N. M.; Chen, Y.; Robben, P. M.; Clapham, G.; Robinson, P. D. J. Org. Chem. 1996, 61, 4508. For the azaferrocenyl series, see: (d) Hansen, J. G.; Søtofte, I.; Johannsen, M. Org. Lett. 2001, 3, 499. (e) Hansen. J. G.; Johannsen, M. J. Org. Chem. 2002, 68, 1266.
20. For ferrocene based monophosphine ligands in Suzuki cross-coupling of aryl chlorides, see: (a) Pickett, T. E.; Richards, C. J. Tetrahedron Lett. 2001, 42, 3767. (b) Liu, S. Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408. (c) Kataoka, N.; Shelby, Q.; Stambuli, J. P. Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (d) Pickett, T. E.; Roca, F. X.; Richards, C. J. J. Org. Chem. 2003, 68, 2592.
21. For ferrocene based monophosphine ligands in Suzuki cross-coupling of aryl chlorides, see: (a) Pickett, T. E.; Richards, C. J. Tetrahedron Lett. 2001, 42, 3767. (b) Liu, S. Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408. (c) Kataoka, N.; Shelby, Q.; Stambuli, J. P. Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (d) Pickett, T. E.; Roca, F. X.; Richards, C. J. J. Org. Chem. 2003, 68, 2592.
22. For ferrocene based monophosphine ligands in Suzuki cross-coupling of aryl chlorides, see: (a) Pickett, T. E.; Richards, C. J. Tetrahedron Lett. 2001, 42, 3767. (b) Liu, S. Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408. (c) Kataoka, N.; Shelby, Q.; Stambuli, J. P. Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (d) Pickett, T. E.; Roca, F. X.; Richards, C. J. J. Org. Chem. 2003, 68, 2592.
23. For ferrocene based monophosphine ligands in Suzuki cross-coupling of aryl chlorides, see: (a) Pickett, T. E.; Richards, C. J. Tetrahedron Lett. 2001, 42, 3767. (b) Liu, S. Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408. (c) Kataoka, N.; Shelby, Q.; Stambuli, J. P. Hartwig, J. F. J. Org. Chem. 2002, 67, 5553. (d) Pickett, T. E.; Roca, F. X.; Richards, C. J. J. Org. Chem. 2003, 68, 2592.
24. (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
25. (b) Gstöttmayr, C. W. K.; Böhm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1363.
26. (c) Wolfe, J. P.; Buchwald, S. P. Angew. Chem., Int. Ed. 1999, 38, 2413.
27. (d) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153.
28. (e) Andreu, M. G.; Zapf, A.; Beller, M. Chem. Commun. 2000, 2475.
29. (f) Botella, L.; Nájera, C. Angew. Chem., Int. Ed. 2002, 41, 179.
30. Yin, J.; Rainka, M. P.; Zhang, X.-X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162.
31. (b) See also: Kočovsky, P.; Vyskoćil, S.; Cĺsařová, I.; Sejbal, J.; Tišlerová, I.; Smrčina, M.; Lloyd-Jones, G. C.; Stephen, S. C.; Butts, C. P.; Murray, M.; Langer, V. J. Am. Chem. Soc. 1999, 121, 7714 and references therein.
32. For the synthesis and charaterization of a Pd complex with a bulky monophosphine ligand, see: Stambuli, J. P.; Bühl, M.; Hartwig, J. J. Am. Chem. Soc. 2002, 124, 9346.
33. (a) Cammidge, A. N.; Crépy, K. V. L. Chem. Commun. 2000, 1723. For other examples, see:
34. For other examples, see: (b) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 12051.
35. After the completion of this manuscript, a paper appeared describing the synthesis of compound 3b by a similar strategy: Herrbach, A.; Marinetti, A.; Baudoin, O.; Guénard, D.; Guéritte, F. J. Org. Chem. 2003, 68, 4897.