A kinetics study of the oxidative addition of bromobenzene to Pd(PCy 3)2 (Cy = cyclohexyl) in a nonpolar medium: The influence on rates of added PCy3 and bromide ion

Organometallics

Volumn 28, Issue 23, 2009, Pages 6732-6738

  Mitchell, Emily A ^a   Jessop, Philip G ^a   Baird, Michael C ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BROMIDE IONS; BROMOBENZENE; CYCLOHEXYL; FIRST-ORDER; FIRST-ORDER CONDITIONS; KINETICS STUDIES; NONPOLAR MEDIUMS; OXIDATIVE ADDITIONS; REACTION UNDER;

IONS; PALLADIUM COMPOUNDS; REACTION KINETICS; TOLUENE;

PALLADIUM;

EID: 71949083796     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900679w     Document Type: Article

References (61)

1. For recent reviews, see: (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4177.
2. (b) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
3. (c) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, Eds.; Wiley: New York, 2002.
4. (d) Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
5. (e) Beletskaya, I. P.; Cheprakov, A. V. In Comprehensive Coordination Chemistry II; McCleverty, J. A., Meyer, T. J., Eds.; Elsevier: Oxford, U.K., 2004; Vol.9, pp 305-368.
6. (f) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
7. (g) Farina, V. Adv. Synth. Catal. 2004, 346, 1553.
8. (h) Bellina, F.; Carpita, A.; Rossi, R. Synthesis 2004, 2419.
9. (i) Tsuji, J. Palladium Reagents and Catalysts, 2nd ed.; Wiley: New York, 2004.
10. (j) Cepanec, I. Synthesis of Biaryls; Elsevier: Amsterdam, 2004.
11. (k) Zapf, A.; Bellier, M. Chem. Commun. 2005, 431.
12. (1) Miyaura, N. In Metal Catalyzed Cross-Coupling Reactions, 2nd ed.; de Mejiere, A., Diederich, F., Eds.; John Wiley & Sons: New York, 2004; pp 41-123.
13. Christmann, U.; Vilar, R. Angew. Chem., Int. Ed. 2005, 44, 366, and references therein.
14. (n) Phan, N. T. S.; Van Der Sluys, M.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 609.
15. (o) Fu, G. C. Acc. Chem. Res. 2008, 41, 1555.
16. (a) Fauvarque, J.-F.; Pflüger, F.; Troupel, M. J. Organomet. Chem. 1981, 208, 419.
17. (b) Amatore, C.; Pflüger, F. Organometallics 1990, 9, 2276.
18. (c) Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 8375.
19. (d) Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1665.
20. (e) Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531.
21. (f) Amatore, C.; Jutand, A.; Khalil, F.; M'Barki, M. A.; Mottier, L. Organometallics 1993, 12, 3168.
22. (g) Jutand, A.; Mosleh, A. Organometallics 1995, 14, 1810.
23. (h) Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373.
24. (i) Jutand, A.; Hii, K. K.; Thomton-Pett, M.; Brown, J. M. Organometallics 1999, 18, 5367.
25. (j) Amatore, C.; Jutand, A.; Thuilliez, A. Organometallics 2001, 20, 3241.
26. (k) Galardon, E.; Ramdeehul, S.; Brown, J. M.; Cowley, A.; Hii, K. K.; Jutand, A. Angew. Chem., Int. Ed. 2002, 41, 1760.
27. (1) AlcazarRoman, L. M.; Hartwig, J. F. Organometallics 2002, 21, 491.
28. (m) Singh, U. K.; Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14104.
29. (n) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 8704.
30. (o) Roy, A. H.; Hartwig, J. F. Organometallics 2004, 23, 194.
31. (p) Jutand, A. Appl. Organomet. Chem. 2004, 18, 574.
32. (q) Shekhar, S.; Ryberg, P.; Hartwig, J. F.; Mathew, J. S.; Blackmond, D. G.; Strieter, E. R.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 3584.
33. (r) Barrios-Landeros, F.; Hartwig, J. H. J. Am. Chem. Soc. 2005, 127, 6944.
34. (s) Shekhar, S.; Hartwig, J. F. Organometallics 2007, 26, 340.
35. (t) Palladino, G.; Madec, D.; Prestat, G.; Maitro, G.; Poli, G.; Jutand, A. Organometallics 2007, 26, 455.
36. (u) SerraMuns, A.; Jutand, A.; Moreno-Mañas, M.; Pleixats, R. Organometallics 2008, 27, 2421.
37. (v) Barrios-Landeros, F. C.; Hartwig, J. H. J. Am. Chem. Soc. 2009, 131, 8141.
38. (a) Kozuch, S.; Shaik, S.; Jutand, A.; Amatore, C. Chem.-Eur. J. 2004, 10, 3072.
39. (b) Senn, H. M.; Ziegler, T. Organometallics 2004, 23, 2980.
40. (c) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
41. (d) Goossen, L. J.; Koley, D.; Hermann, H. L.; Thiel, W. Organometallics 2005, 24, 2398.
42. (e) Kozuch, S.; Amatore, C.; Jutand, A.; Shaik, S. Organometallics 2005, 24, 2319.
43. (f) Goossen, L. J.; Koley, D.; Hermann, H. L.; Thiel, W. Organometallics 2006, 25, 54.
44. (g) Ahlquist, M.; Fristrup, P.; Tanner, D.; Norrby, P.-O. Organometallics 2006, 25, 2066.
45. (h) Ariafard, A.; Lin, Z. Organometallics 2006, 25, 4030.
46. (i) Braga, A. A. C.; Ujaque, G.; Maseras, F. Organometallics 2006, 25, 3662.
47. (j) Ahlquist, M.; Norrby, P.-O. Organometallics 2007, 26, 550.
48. (k) Lam, K. C.; Marder, T. B.; Lin, Z. Organometallics 2007, 26, 758.
49. (1) Barder, T. E.; Biscoe, M. R.; Buchwald, S. L. Organometallics 2007, 26, 2183.
50. (m) Li, Z.; Fu, Y.; Guo, Q.-X.; Liu, L. Organometallics 2008, 27,4043.
51. (n) Surawatanawong, P.; Fan, Y.; Hall, M. B. J. Organomet. Chem. 2008, 693, 1552.
52. (a) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A.; Meyer, G. Organometallics 1995, 14, 5605.
53. (b) Amatore, C.; Jutand, A. J. Organomet. Chem. 1999, 576, 254.
54. (c) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314.
55. (d) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009.
56. (e) Amatore, C.; Jutand, A.; Lematre, R; Ricard, J. L.; Kozuch, S.; Shaik, S. J. Organomet. Chem. 2004, 689, 3728.
57. Mitchell, E. A.; Baird, M. C. Organometallics 2007, 26, 5230.
58. Tatsuno, Y.; Yoshida, T.; Otsuka, S. Inorg. Synth. 1990, 28, 342.
59. Stambuli, J. P.; Incarvito, C. D.; Bühl, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 1184.
60. GraphPad Prism, Version 3.02; GraphPad Software: La Jolla, CA, 2006.
61. Tolman, C. A. Chem. Rev. 1977, 77, 313.