Oxidative addition of aryl chlorides to monoligated palladium(0): A DFT-SCRF study

Organometallics

Volumn 26, Issue 3, 2007, Pages 550-553

  Ahlquist, Mårten ^a   Norrby, Per Ola ^b  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ELECTRON TRANSITIONS; OXIDATION; PALLADIUM; REACTION KINETICS; SUBSTITUTION REACTIONS;

DENSITY FUNCTIONAL THEORY (DFT); OXIDATIVE ADDITION; PRE-REACTIVE COMPLEXES;

AROMATIC COMPOUNDS;

EID: 33847182815     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0604932     Document Type: Article

References (38)

1. (a) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636.
2. (b) Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437.
3. (c) Negishi, E.; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel, B. I. J. Am. Chem. Soc. 1978, 100, 2254.
4. (d) Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
5. (e) Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320.
6. (f) Cacchi, S.; Felici, M.; Pietroni, B. Tetrahedron Lett. 1984, 25, 3137.
7. (g) Trost, B. M.; Schmidt, T. J. Am. Chem. Soc. 1988, 110, 2301.
8. (h) For a recent review on palladium catalysis in total synthesis see: Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442.
9. Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
10. (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
11. (b) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2875.
12. (a) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
13. (b) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
14. (c) Barrios-Landeros, F.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 6944.
15. (a) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 8704.
16. (b) Hansen, A. L.; Ebran, J.-P.; Ahlquist, M.; Norrby, P.-O.; Skrydstrup, T. Angew. Chem., Int. Ed. 2006, 45, 3349.
17. (a) Low, J. J.; Goddard, W. A., III. J. Am. Chem. Soc. 1986, 108, 6115.
18. (b) Ananikov, V. P.; Musaev, D. G.; Morokuma, K. Organometallics 2005, 24, 715.
19. (c) Sakaki, S.; Biswas, B.; Sugimoto, M.; J. Chem. Soc., Dalton Trans. 1997, 803.
20. (d) Sakaki, S.; Kai, S.; Sugimoto, M. Organo-metallics 1999, 18, 4825.
21. (e) Sumimoto, M.; Iwane, N.; Takahama, T.; Sakaki, S. J. Am. Chem. Soc. 2004, 126, 10457.
22. (a) Senn, H. M.; Ziegler, T. Organometallics 2004, 23, 2980.
23. (b) Goossen, L. J.; Koley, D.; Hermann, H.; Thiel, W. Chem. Commun. 2004, 2141.
24. (c) Goossen, L. J.; Koley, D.; Hermann, H.; Thiel, W. Organometallics 2005, 24, 2398.
25. (d) Cundari, T. R.; Deng, J. J. Phys. Org. Chem. 2005, 18, 417.
26. (e) Kozuch, S.; Amatore, C.; Jutand, A.; Shaik, S. Organometallics 2005, 24, 2319.
27. (f) Braga, A. A. C.; Ujaque, G.; Maseras, F. Organometallics 2006, 25, 3647.
28. DFT calculations were carried out with the Jaguar 4.2 program package from Schrödinger Inc., Portland, OR (http://www.scnrodinger.com). All of the calculations were performed at the B3LYP/LACVP* level. The geometries were fully optimized in solvent, simulated with the PB-SCRF model: Marten, B.; Kim, K.; Cortis, C.; Friesner, R. A.; Murphy, R. B.; Ringnalda, M. N.; Sitkoff, D.; Honig, B. J. Phys. Chem. 1996, 100, 11775. The parameters were set to ε = 38 probe radius = 2.48 to simulate DMF.
29. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 37, 3387.
30. Ahlquist, M.; Fristrup, P.; Tanner, D.; Norrby, P.-O. Organometallics 2006, 25, 2066.
31. Weinhold, F.; Landis, C. Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective; Cambridge University Press: Cambridge, U.K., 2005.
32. Christmann, U.; Vilar, R. Angew. Chem., Int. Ed. 2005, 44, 366.
33. (a) Ahlquist, M.; Fabrizi, G.; Cacchi, S.; Norrby, P.-O. Chem. Commun. 2005, 4196.
34. (b) Ahlquist, M.; Fabrizi, G.; Cacchi, S.; Norrby, P.-O. J. Am. Chem. Soc. 2006, 128, 12785.
35. Fristrup, P.; Jensen, T.; Hoppe, J.; Norrby, P.-O. Chem. Eur. J. 2006, 12, 5352.
36. (a) Böhm, V. P. W.; Herrmann, W. A. Chem. Eur. J. 2001, 7, 4191.
37. (b) de Vries, A. H. M.; Parlevliet, F. J.; Schmieder-van der Vondervoort, L.; Mommers, J. H. M.; Henderickx, H. J. W.; Walet, M. A. M.; de Vries, J. G. Adv. Synth. Catal. 2002, 344, 996.
38. We have avoided comparing the anionic and neutral paths directly, due to the fact that the solvation of small anions sometimes gives results not accurate enough for such a comparison to be reasonable. Due to the cancellation of errors, a comparison of complexes of the same overall charge should yield more reliable results. Ahlquist, M.; Kozuch, S.; Shaik, S.; Tanner, D.; Norrby, P.-O. Organometallics 2006, 25, 45.