Dioxygen activation by a low-valent cobalt complex employing a flexible tripodal N-heterocyclic carbene ligand

Journal of the American Chemical Society

Volumn 126, Issue 41, 2004, Pages 13464-13473

  Hu, Xile ^a   Castro Rodriguez, Ingrid ^a   Meyer, Karsten ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CARBON MONOXIDE; COBALT COMPOUNDS; INFRARED SPECTROSCOPY; MAGNETIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PROBABILITY DENSITY FUNCTION; SQUIDS; ULTRAVIOLET SPECTROSCOPY;

DENSITY FUNCTIONAL THEORY (DFT); DIOXYGEN ACTIVATION; OXIDIZERS; OXYGEN TRANSFER REACTIONS;

ORGANOMETALLICS;

BENZENE DERIVATIVE; BENZENECARBONYL CHLORIDE; CARBENE; CARBON MONOXIDE; COBALT COMPLEX; DICHLOROMETHANE; HETEROCYCLIC AMINE; IMIDAZOLE DERIVATIVE; LIGAND; OXYGEN; PHOSPHINE DERIVATIVE; TRIS[2 (3 XYLENYLIMIDAZOL 2 YLIDENE)ETHYL]AMINE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; INFRARED SPECTROSCOPY; MAGNETISM; PROTON NUCLEAR MAGNETIC RESONANCE; SOLUBILITY; SUPERCONDUCTOR; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

COBALT; HETEROCYCLIC COMPOUNDS; HYDROCARBONS; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; METHANE; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; OXYGEN; PHOSPHINES; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 6044252413     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046048k     Document Type: Article

References (95)

1. Cummins, C. C.; Lee, J.; Schrock, R. R.; Davis, W. D. Angew. Chem., Int. Ed. Engl 1992, 31, 1501-1503.
2. Yandulov, D. V.; Schrock, R. R. Science 2003, 301, 76-78.
3. Yandulov. D. V.; Schrock, R. R. J. Am. Chem. Soc. 2002, 124, 6252-6253.
4. Yandulov, D. V.; Schrock, R. R.; Rheingold. A. L.; Ceccarelli, C.; Davis, W. M. Inorg. Chem. 2003, 42, 796-813.
5. MacBeth, C. E.; Golombek, A. P.; Young, V. G.; Yang, C.; Kuczera, K.; Hendrich, M. P.; Borovik, A. S. Science 2000, 289, 938-941.
6. Jenkins, D. M.; Betley, T. A.; Peters, J. C. J. Am. Chem. Soc. 2002, 124, 11238-11239.
7. Brown, S. D.; Betley, T. A.; Peters, J. C. J. Am. Chem. Soc. 2003, 125, 322-323.
8. Betley, T. A.; Peters, J. C. J. Am. Chem. Soc. 2004, 126, 6252-6254.
9. Kernbach, U.; Ramm, M.; Luger, P.; Fehlhammer, W. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 310-312.
10. Peris, E.; Loch, J. A.; Mata, J.; Crabtree, R. H. Chem. Commun. 2001, 201-202.
11. Arnold, P. L.; Scarisbrick, A. C.; Blake, A. J.; Wilson, C. Chem. Commun. 2001, 2340-2341.
12. Danopoulos, A. A.; Winston, S.; Motherwell, W. B. Chem. Commun. 2002, 1376-1377.
13. Hu, X.; Castro-Rodriguez, I.; Meyer, K. Organometallics 2003, 22, 3016-3018.
14. Hu, X.; Tang, Y.; Gantzel, P.; Meyer, K. Organometallics 2003, 22, 612-614.
15. Hu, X.; Castro-Rodriguez, I.; Meyer, K. J. Am. Chem. Soc. 2003, 125, 12237-12245.
16. Douthwaite, R. E.; Houghton, J.; Kariuki, B. M. Chem. Commun. 2004, 698-699.
17. Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363.
18. Herrmann, W. A.; Kocher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2163-2187.
19. Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
20. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1291-1309.
21. Herrmann, W. A.; Elison, M.; Fischer, J.; Kocher, C.; Artus, G. R. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2371-2374.
22. Gstottmayr, C. W. K.; Bohm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1363-1365.
23. Scholl, M.; Ding, S.; Lee. C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
24. Huang, J. K.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678.
25. Solomon, E. I.; Brunold, T. C.; Davis, M. I.; Kemsley, J. N.; Lee, S. K.; Lehnen, N.; Neese, F.; Skulan, A. J.; Yang, Y. S.; Zhou, J. Chem. Rev. 2000, 100, 235-349.
26. Solomon, E. I.; Chen, P.; Metz, M.; Lee, S. K.; Palmer, A. E. Angew. Chem., Int. Ed. 2001, 40, 4570-4590.
27. Que, L.; Ho, R. Y. N. Chem. Rev. 1996, 96, 2607-2624.
28. Que, L.; Tolman, W. B. Angew. Chem., Int. Ed. 2002, 41, 1114-1137.
29. Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104, 1047-1076.
30. Kim, E.; Chufan, E. E.; Kamaraj, K.; Karlin, K. D. Chem. Rev. 2004, 104, 1077-1133.
31. Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidation of Organic Compounds; Academic Press: New York, 1981
32. Martell, A. E., Sawyer, D. T., Eds. Oxygen Complexes and Oxygen Activation by Transition Metals; Plenum Press: New York, 1988.
33. Simandi, L. I., Ed. Advances in Catalytic Activation of Dioxygen by Metal Complexes; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2003.
34. Busch, D. H.; Alcock, N. W. Chem. Rev. 1994, 94, 585-623.
35. Hanzlik, R. P.; Williamson, D. J. Am. Chem. Soc. 1976, 98, 6570-6573.
36. Reetz, M. T.; Tollner, K. Tetrahedron Lett. 1995, 36, 9461-9464.
37. Jain, S. L.; Sain, B. Angew. Chem., Int. Ed. 2003, 42, 1265-1267.
38. Reinaud, O. M.; Yap, G. P. A.; Rheingold, A. L.; Theopold, K. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2051-2052.
39. Brown, L. D.; Raymond, K. N. Inorg. Chem. 1975, 14, 2595-2601.
40. Gall, R. S.; Rogers, J. F.; Schaefer, W. P.; Christoph, G. G. J. Am. Chem. Soc. 1976, 95, 5135-5144.
41. Schaefer, W. P.; Huie, B. T.; Kurilla, M. G.; Ealick, S. E. Inorg. Chem. 1980, 19, 340-344.
42. Jameson, G. B.; Robinson, W. T.; Rodley. G. A. J. Chem. Soc., Dalton Trans. 1978, 191-196.
43. Cini, R.; Orioli, P. J. Chem. Soc., Chem. Commun. 1981, 196-198.
44. Hohenester, E.; Kratky, C.; Krautler, B. J. Am. Chem. Soc. 1991, 113, 4523-4530.
45. Busch, D. H.; Jackson, P. J.; Kojima, M.; Chmielewski, P.; Matsumoto, N.; Stevens, J. C.; Wu, W.; Nosco, D.; Herron, N.; Ye, N. D.; Warburton, P. R.; Masarwa, M.; Stephenson, N. A.; Christoph, G.; Alcock, N. W. Inorg. Chem. 1994, 33, 910-923.
46. Terry, N. W.; Amma. E. L.; Vaska, L. J. Am. Chem. Soc. 1972, 94, 653-655.
47. Halpern, J.; Goodall, B. L.; Khare, G. P.; Lim, H. S.; Pluth, J. J. J. Am. Chem. Soc. 1975, 97, 2301-2303.
48. Crump, D. B.; Stepaniak, R. F.; Payne, N. C. Can. J. Chem 1977, 55, 438-446.
49. Ohishi, T.; Kashiwabara, K.; Fujita, J.; Ohba, S.; Ishii, T.; Saito, Y. Bull. Chem. Soc. Jpn. 1986, 59, 385-393.
50. Egan, J. W.; Haggerty, B. S.; Rheingold, A. L.; Sendlinger, S. C.; Theopold, K. H. J. Am. Chem. Soc. 1990, 112, 2445-2446.
51. Dioxygen reactivity of a nickel(II) NHC complex has been reported; see Dible, B. R.; Sigman, M. S. J. Am. Chem. Soc. 2003, 125, 872-873.
52. Stahl and co-workers recently synthesized a palladium(II) peroxo complex with two monodentate NHCs as supporting ligands; see Konnick, M. M.; Guzel, L. A.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126, 10212-10213.
53. Nakamoto, K. Infrared and Roman Spectra of Inorganic and Coordination Compounds, 5th ed.; John Wiley & Sons: New York, 1997; Vol. 2.
54. Simms, R. W.; Drewitt, M. J.; Baird, M. C. Organometallics 2002, 21, 2958-2963.
55. Gibson, S. E.; Johnstone, C.; Loch, J. A.; Steed, J. W.; Stevenazzi, A. Organometallics 2003, 22, 5374-5377.
56. van Rensburg, H.; Tooze, R. P.; Foster, D. F.; Slawin, A. M. Z. Inorg. Chem. 2004, 43, 2468-2470.
57. Jewson, J. D.; Liable-Sands, L. M.; Yap, G. P. A.; Rheingold, A. L.; Theopold, K. H. Organometattics 1999, 18, 300-305.
58. Boudreaux, E. A.; Mulay, L. N. Theory and Applications of Molecular Paramagnetism; John Wiley & Sons: New York, 1976; pp P217-219.
59. Cotton, F. A.; Wilkinson, G.; Murillo, C. A.; Bochmann, M. Advanced Inorganic Chemistry, 6th ed.; John Wiley & Sons: New York, 1999; pp P820-821.
60. Jenkins, D. M.; Di Bilio, A. J.; Allen, M. J.; Betley, T. A.; Peters, J. C. J. Am. Chem. Soc. 2002, 124, 15336-15350.
61. Drago, R. S. Physical Methods for Chemists, 2nd ed.; Surfside Scientific Publishers: Gainesville, FL, 1992; p P486.
62. Jones, R. D.; Summerville, D. A.; Basolo, F. Chem. Rev, 1979, 79, 139-179.
63. Cramer, C. J.; Tolman. W. B.; Theopold, K. H.; Rheingold, A. L. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 3635-3640.
64. Ballistreri, F. P.; Tomaselli, G. A.; Toscano, R. M.; Conte, V.; Difuria, F. J. Am. Chem. Soc. 1991, 113, 6209-6212.
65. Adam, W.; Haas, W.; Lohray, B. B. J. Am. Chem. Soc. 1991, 113, 6202-6208.
66. Kitajima, N.; Morooka, Y. Chem. Rev. 1994, 94, 737-757.
67. Sisemore, M. F.; Selke, M.; Burstyn, J. N.; Valentine, J. S. Inorg. Chem. 1997, 36, 979-984.
68. Sheldon, R. A.; Vandoorn, J. A. J. Organomet. Chem. 1975, 94, 115-129.
69. Sisemore, M. F.; Burstyn, J. N.; Valentine, J. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 206-208.
70. - with acylating agents; see Khenkin, A. M.; Shteinman, A. A. J. Chem. Soc., Chem. Commun. 1984, 1219-1220.
71. The fate of the chlorine radical generated in this reaction is not clear. Formation of Co(II)-Cl species was not observed.
72. Mimoun, H. J. Mol. Catal. 1980, 7, 1-29.
73. Regen, S. L.; Whitesides, G. M. J. Organomet. Chem. 1973, 59, 293-297.
74. Mayer, H. A.; Kaska, W. C. Chem. Rev. 1994, 94, 1239-1272.
75. Sacconi, L.; Bertini, I. J. Am. Chem. Soc. 1968, 90, 5443-5446.
76. Sacconi, L.; Ghilardi, C. A.; Mealli, C.; Zanobini, F. Inorg. Chem. 1975, 14, 1380-1386.
77. Ghilardi, C. A.; Midollini, S.; Sacconi, L. Inorg. Chem. 1975, 14, 1790-1795.
78. Ghilardi, C. A.; Sabatini, A.; Sacconi, L. Inorg. Chem. 1976, 15, 2763-2767.
79. Betley, T. A.; Peters, J. C. Inorg. Chem. 2003, 42, 5074-5084.
80. Basuli, F.; Bailey, B. C.; Tomaszewski, J.; Huffman, J. C.; Mindiola, D. J. J. Am. Chem. Soc. 2003, 125, 6052-6053.
81. Holland, P. L.; Tolman, W. B. J. Am. Chem. Soc. 1999, 121, 7270-7271.
82. Spencer, D. J. E.; Aboelella, N. W.; Reynolds, A. M.; Holland, P. L.; Tolman, W. B. J. Am. Chem. Soc. 2002, 124, 2108-2109.
83. Smith, J. M.; Lachicotte, R. J.; Pittard, K. A.; Cundari, T. R.; Lukat-Rodgers, G.; Rodgers, K. R.; Holland, P. L. J. Am. Chem. Soc. 2001, 123, 9222-9223.
84. Dai, X. L.; Warren, T. H. Chem. Commun. 2001, 1998-1999.
85. Dai, X. L.; Kapoor, P.; Warren, T. H. J. Am. Chem. Soc. 2004, 126, 4798-4799.
86. O'Connor, C. J. Prog. Inorg. Chem. 1982, 29, 203-283.
87. ADF2003.01; SCM, Theoretical Chemistry, Vrijie Universiteit: Amsterdam, The Netherlands.
88. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211.
89. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
90. Perdew. J. P. Phys. Rev. B 1986, 33, 8822-8824.
91. Van Lenthe, E.; Ehlers, A.; Baerends, E. J. J. Chem. Phys. 1999, 110, 8943-8953.
92. Snijders, J. G.; Vernooijs, P.; Baerends, E. J. At. Data Nucl. Tables 1981, 26, 483-509.
93. Ward, K. J. Am. Chem. Soc. 1935, 57, 914-916.
94. Arduengo, A. J.; Gentry, F. P.; Taverkere, P. K.; Simmons, H. E. U.S. Patent 6177575, 2001.
95. Spek, A. L. J. Appl. Cryst. 2003, 36, 7-13.