A critical analysis of the cyclic and open alternatives of the transmetalation step in the stille cross-coupling reaction

Journal of the American Chemical Society

Volumn 128, Issue 45, 2006, Pages 14571-14578

  Nova, Ainara ^a   Ujaque, Gregori ^a   Maseras, Feliu ^a,b   Lledós, Agustí ^a   Espinet, Pablo ^c  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^b INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^c UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DISSOCIATION; MATHEMATICAL MODELS; METAL ANALYSIS; PROBABILITY DENSITY FUNCTION; SUBSTITUTION REACTIONS;

LIGANDS; ORGANOTRIFLATE SYSTEMS; STILLE CROSS COUPLING REACTION; TRANSMETALATION;

REACTION KINETICS;

ARSINE DERIVATIVE; BROMINE DERIVATIVE; CHLOROBENZENE; LIGAND; ORGANOHALOGEN DERIVATIVE; PALLADIUM; PHOSPHINE; SOLVENT; TETRAHYDROFURAN; TIN DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; TRIPHENYLARSINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CIS TRANS ISOMERISM; CYCLIZATION; DENSITY FUNCTIONAL THEORY; DISSOCIATION; LIGAND BINDING; MODEL; REACTION ANALYSIS; SOLVENT EFFECT; STILLE REACTION; TRANSMETALATION;

EID: 33750988497     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0635736     Document Type: Article

References (53)

1. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-523.
2. Diederich, F.; de Mejiere, A. Metal Catalyzed Cross-Coupling Reaccions; John Wiley & Sons: New York, 2004.
3. Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704-4734.
4. Tamao, K.; Miyaura, N. In Cross-Coupling Reactions: Topics in Current Chemistry, Vol. 219; Springer: Berlin, 2002: pp 1-9.
5. Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636-3638.
6. Farina, V.; Krishnamurthy, W. K. Organic Reactions; Wiley: New York, 1997; Vol. 50.
7. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442-4489.
8. Senn, H. M.; Ziegler, T. Organometallics 2004, 23, 2980-2988.
9. Ananikov, V. P.; Musaev, D. G.; Morokuma, K. Organometallics 2005, 24, 715-723.
10. Goossen, L. J.; Koley, D.; Hermann, H.; Thiel, W. Chem. Commun. 2004, 2141-2143.
11. Kozuch, S.; Shaik, S.; Jutand, A.; Amatore, C. Chem.-Eur. J. 2004, 10, 3072-3080.
12. Kozuch, S.; Amatore, C.; Jutand, A.; Shaik, S. Organometallics 2005, 24, 2319-2330.
13. Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978-8985.
14. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
15. Casado, A. L.; Espinet, P.; Gallego, A. M. J. Am. Chem. Soc. 2000, 122, 11771-11782.
16. Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434-5444.
17. Casado, A. L.; Espinet, P.; Gallego, A. M.; Martinez-Ilarduya, J. M. Chem. Commun. 2001, 339-340.
18. Ujaque, G.; Maseras, F. Struct. Bonding 2004, 112, 117-149.
19. Maseras, F.; Lledos, A. Computational Modeling of Homogeneous Catalysis; Kluwer Academic Publishers: Dordrecht, The Netherlands 2002; Vol. 25.
20. Napolitano, E.; Farina, V.; Persico, M. Organometallics 2003, 22, 4030-4037.
21. Alvarez, R.; Faza, O. N.; Lopez, C. S.; de Lera, A. R. Org. Lett. 2006, 8, 35-38.
22. Braga, A. A. C.; Morgon, N. H.; Ujaque, G.; Maseras, F. J. Am. Chem. Soc. 2005, 127, 9298-9307.
23. Goossen, L. J.; Koley, D.; Hermann, H. L.; Thiel, W. J. Am. Chem. Soc. 2005, 127, 11102-11114.
24. Goossen, L. J.; Koley, D.; Hermann, H. L.; Thiel, W. Organometallics 2005, 24, 2398-2410.
25. Sumimoto, M.; Iwane, N.; Takahama, T.; Sakaki, S. J. Am. Chem. Soc. 2004, 126, 10457-10471.
26. Balcells, D.; Maseras, F.; Keay, B. A.; Ziegler, T. Organometallics 2004, 23, 2784-2796.
27. Albert, K.; Gisdakis, P.; Rosch, N. Organometallics 1998, 17, 1608-1616.
28. Sundermann, A.; Uzan, O.; Martin, J. M. L. Chem.-Eur. J. 2001, 7, 1703-1711.
29. von Schenck, H.; Akermark, B.; Svensson, M. Organometallics 2002, 21, 2248-2253.
30. Matsubara, T. Organometallics 2003, 22, 4286-4296.
31. Amatore, C.; Jutand, A.; Lemaitre, F.; Ricard, J. L.; Kozuch, S.; Shaik, S. J. Organomet. Chem. 2004, 689, 3728-3734.
32. Cundari, T. R.; Deng, J.; Zhao, Y. J. Mol. Struct.; THEOCHEM 2003, 632, 121-129.
33. Eberhardt, J. K.; Frohlich, R.; Wurthwein, E. U. J. Org. Chem. 2003, 68, 6690-6694.
34. Goossen, L. J.; Koley, D.; Hermann, H. L.; Thiel, W. Organometallics 2006, 25, 54-67.
35. Kozuch, S.; Shaik, S. J. Am. Chem. Soc. 2006, 128, 3355-3365.
36. Braga, A. A. C.; Ujaque, G.; Maseras, F. Organometallics 2006, 25, 3647-3658.
37. Lee, C.; Parr, R. G.; Yang, W. Phys. Rev. B 1988, 37, B785.
38. Becke, A. D. J. Phys. Chem. 1993, 98, 648.
39. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
40. Frisch, M. J.; et al. Gaussian 03; Gaussian, Inc.: Wallingford, CT, 2004.
41. Hay, P. J.; Wadt, W. R. J. Phys. Chem. 1985, 82, 299.
42. Wadt, W. R.; Hay, P. J. J. Phys. Chem. 1985, 82, 284.
43. Höllwarth, A.; Böhme, M.; Dapprich, S.; Ehlers, A. W.; Gobbi, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 237.
44. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Phys. Chem. A 1972, 56, 2257.
45. Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; Defrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 3654-3665.
46. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 3265-3269.
47. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995.
48. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Comput. Chem. 2003, 24, 669.
49. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027.
50. Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959.
51. Amatore, C.; Bahsoun, A. A.; Jutand, A.; Meyer, G.; Ntepe, A. N.; Ricard, L. J. Am. Chem. Soc. 2003, 125, 4212-4222.
52. An intermediate of type 9t has been reported as spectroscopically observed in a reversible tin-to-palladium transmetalation of 2-furyl using 2-tributylstannylfuran: Cotter, W. D.; Barbour, L. K.; McNamara, L.; Hechter, R.; Lachicotte R. J. J. Am. Chem. Soc. 1998, 120, 11016-11017.
53. Casares, J. A.; Espinet, P.; Salas, G. Chem.-Eur. J. 2002, 8, 4843-4853.