Mechanism for activation of molecular oxygen by cis- And trans-(pyridine) 2Pd(OAc)H: Pd 0 versus direct insertion

Journal of the American Chemical Society

Volumn 131, Issue 4, 2009, Pages 1416-1425

  Keith, Jason M ^a   Goddard III, William A ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CIS AND TRANS ISOMERS; CIS/TRANS ISOMERIZATION; DIOXYGEN; H-BONDS; MONODENTATE LIGANDS; PALLADIUM HYDRIDE; QUANTUM MECHANICS; REDUCTIVE ELIMINATION;

ISOMERS; LIGANDS; MOLECULAR OXYGEN; PALLADIUM COMPOUNDS; POTENTIAL ENERGY; POTENTIAL ENERGY SURFACES; PYRIDINE; QUANTUM CHEMISTRY; QUANTUM THEORY; TOLUENE;

PALLADIUM;

LIGAND; OXYGEN; PALLADIUM COMPLEX; PYRIDINE; TOLUENE;

ARTICLE; CATALYSIS; ELECTRIC POTENTIAL; HYDROGEN BOND; OXIDATION; QUANTUM MECHANICS; TRANS ISOMER;

EID: 67849133067     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8040459     Document Type: Article

References (62)

1. (a) Nishimura, T.; Uemura, S. Synlett 2004, 2, 201.
2. (b) Stahl, S. S. Angew. Chem, Int. Ed. 2004, 43, 3400.
3. Gligorich, K. M.; Sigman. M. S. Angew. Chem., Int. Ed. 2006, 45, 6612.
4. Stoltz, B. M. Chem. Lett. 2004, 362.
5. (e) Sigman, M. S.; Schultz, M. J. Org. Biomol. Chem. 2004, 2, 2551.
6. (f) Stahl, S. Science 2005, 309, 1824.
7. (g) Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221.
8. (h) Sheldon, R. A.; Arends, I. W. C. E.; ten Brink, G.-J.; Dijksman, A. Acc. Chem. Res. 2002, 35, 774.
9. Toyota, M.; Ihara, M. Synlett 2002, 1211.
10. (a) Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221.
11. (b) Bagdanoff, J. T.; Stoltz, B. M. Angew. Chem., Int. Ed. 2004, 43, 353.
12. Jensen, D. R.; Schultz, M. J.; Mueller, J. A.; Sigman, M. S. Angew. Chem., Int. Ed. 2003, 42, 3810.
13. Schultz, M. J.; Park, C. C.; Sigman, M. S. Chem. Commun. 2002, 3034.
14. (e) Bagdanoff, J. T.; Ferreira, E. M.; Stoltz, B. M. Org. Lett. 2003, 5, 835.
15. (f) Jensen, D. R.; Sigman, M. S. Org. Lett. 2003, 5, 63.
16. (g) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725.
17. (h) Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4, 4179.
18. (a) Rogers, M. M.; Wendlandt, J. E.; Guzei, I. A.; Stahl, S. S. Org. Lett. 2006, 8, 2257.
19. (b) Lee, J. M.; Ahn, D. S.; Jung, D. Y.; Lee, J.; Do, Y.; Kim, S. K.; Chang, S. K. J. Am. Chem. Soc. 2006, 128, 12954.
20. Streuff, J.; Hovelmann, C. H.; Nieger, M.; Muniz, K. J. Am. Chem. Soc. 2005, 127, 14586.
21. Brice, J. L.; Harang, J. E.; Timokhin, V. I.; Anastasi, N. R.; Stahl, S. S. J. Am. Chem. Soc. 2005, 127, 2868.
22. (e) Timokhin, V. I.; Anastasi, N. R.; Stahl, S. S. J. Am. Chem. Soc. 2003, 125, 12996.
23. (a) Nishimura, T.; Araki, H.; Maeda, Y.; Uemura, S. Org. Lett. 2003, 5, 2997.
24. (b) Matsumura, S.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2003, 125, 8862.
25. Nishimura, T.; Matsumura, S.; Maeda, Y.; Uemura, S. Tetrahedron Lett. 2002, 43, 3037.
26. Nishimura, T.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 2645.
27. (a) Piera, J.; Narhi, K.; Backvall, J. E. Angew. Chem., Int. Ed. 2006, 45, 6914.
28. (b) Trend, R. M.; Ramtohul, Y. K.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2003, 42, 2892.
29. Bianchi, D.; Bortolo, R.; D'Aloisio, R.; Ricci, M. Angew. Chem., Int. Ed. 1999, 38, 706.
30. (a) Keith, J. M.; Nielsen, R. J.; Oxgaard, J.; Goddard, W. A., III. J.Am. Chem. Soc. 2005, 127, 13172.
31. (b) Keith, J. M.; Muller, R. P.; Kemp, R. A.; Goldberg, K. I.; Goddard, W. A., III. Inorg. Chem. 2006, 45, 9631.
32. Keith, J. M.; Goddard, W. A., III.; Oxgaard, J. J. Am. Chem. Soc. 2007, 129, 10361.
33. (a) Denny, M. C.; Smythe, N. A.; Cetto, K. L.; Kemp, R. A.; Goldberg, K. I. J. Am. Chem. Soc. 2006, 128, 2508.
34. (b) A second paper appearing shortly after that also reports insertion of molecular oxygen into a PdII-H bond: Konnick, M. M.; Gandhi, B. A.; Guzei, I. A.; Stahl, S. S. Angew. Chem., Int. Ed. 2006, 45, 2904.
35. IIIH-superoxide. These pathways have been eliminated due to unreasonably high-energy intermediates and will not be examined here. For a thorough examination of all four of these pathways, see: Popp, B. V.; Stahl, S. S. J. Am. Chem. Soc. 2007, 129, 4410.
36. (a) Konnick, M. M.; Guzei, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126, 10212.
37. (b) Stahl, S. S.; Thorman, J. L.; Nelson, R. C.; Kozee, M. A. J. Am. Chem. Soc. 2001, 123, 7188.
38. Clegg, W.; Eastham, G. R.; Elsegood, M. R. J.; Heaton, B. T.; Iggo, J. A.; Tooze, R. P.; Whyman, R.; Zacchini, S. J.Chem Soc,Dalton,Trans. 2002, 3300.
39. Landis, C. R.; Morales, C. M.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126, 16302.
40. (e) Popp, B. V.; Wendlandt, J. E.; Landis, C. R.; Stahl, S. S. Angew. Chem., Int. Ed. 2007, 46, 601.
41. Nielsen, R. J.; Keith, J. M.; Stoltz, B. M.; Goddard, W. A., III. J. Am. Chem. Soc. 2004, 126, 7967.
42. (a) Jaguar 7.0; Schrodinger, Inc.: Portland, OR, 2005.
43. (b) See, for example: Greeley, B. H.; Russo, T. V.; Mainz, D. T.; Friesner, R. A.; Langlois, J.-M.; Goddard, W. A.; Donnelly, R. E.; Ringnalda, M. N. J. Chem. Phys. 1994, 101, 4028.
44. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
45. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev.B 1988, 37, 785.
46. Baker, J.; Muir, M.; Andzelm, J.; Scheiner, A. In Chemical Applications of Density-Functional Theory; Laird, B. B., Ross, R. B., Ziegler, T., Eds.; ACS Symposium Series 629; American Chemical Society: Washington, DC, 1996.
47. Niu, S.; Hall, B. M. Chem Rev. 2000, 100, 353.
48. (a) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
49. (b) Goddard, W. A., III. Phys Rev. 1968, 174, 659.
50. Melius, C. F.; Olafson, B. O.; Goddard, W. A., III. Chem. Phys. Lett. 1974, 28, 457.
51. (a) Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 16, 217.
52. (b) 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, 77, 3654.
53. (a) Tannor, D. J.; Marten, B.; Murphy, R.; Friesner, R. A.; Sitkoff, D.; Nicholls, A.; Ringnalda, M.; Goddard, W. A., III.; Honig, B. J. Am. Chem. Soc. 1994, 116, 11875.
54. (b) 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.
55. (a) Truong, T. N.; Truong, T. T.; Stefanovich, E. V. J. Chem. Phys. 1997, 107, 1881.
56. (b) Cramer, C. J.; Thrular, D. G. Chem Rev. 1999, 99, 2161.
57. Oxgaard, J.; Muller, R. P.; Periana, R. A.; Goddard, W. A., III. J. Am. Chem. Soc. 2004, 126, 352.
58. (a) Xu, X.; Goddard, W. A. Proc. Natl. Acad. Sci. U.S.A. 1996, 99, 15308.
59. (b) Wittbrodt, J. M.; Schlegel, H. B. J. Chem. Phys. 1996, 105, 6574.
60. For methods on correcting spin contamination in DFT, see: Bally, T.; Borden, W. T. Rev. Comput. Chem. 1999, 13, 1.
61. For both cases the free pyridine in 2 was systematically brought closer to the Pd while being forced to remain 90° from the H for the trans case and 90° from the other pyridine for the cis case.
62. 2PdHOAc from ref 8 discussed in section 1.