Activation of nitroarenes in the homogenous catalytic carbonylation of nitroaromatics via an oxygen-atom-transfer mechanism induced by inner-sphere electron transfer

Journal of the American Chemical Society

Volumn 119, Issue 45, 1997, Pages 11049-11060

  Skoog, Steven J ^a   Gladfelter, Wayne L ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC NITRO COMPOUND; OXYGEN; RUTHENIUM COMPLEX;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; ELECTRON TRANSPORT; REACTION ANALYSIS;

EID: 0030700933     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971899w     Document Type: Article

References (97)

1. Cenini, S.; Pizzotti, M.; Crotti, C. In Aspects of Homogeneous Catalysis; Ugo, R., Ed.; Reidel: Dordrecht, 1988; Vol. 6, pp 97-198.
2. Bhaduri, S.; Sharma, K. R.; Khwaja, H. I. Proc. Indian Acad. Sci., Chem. Sci. 1989, 104, 195.
3. Cenini, S.; Pizzotti, M.; Crotti, C.; Porta, F.; La Monica, G. J. Chem. Soc., Chem. Commun. 1984, 1286.
4. Cenini, S.; Crotti, C.; Pizzotti, M.; Porta, F. J. Org. Chem. 1988, 53, 1243.
5. Cenini, S.; Pizzotti, M.; Crotti, C.; Ragaini, F.; Porta, F. J. Mol. Catal. 1988, 49, 59.
6. Gargulak, J. D.; Noirot, M. D.; Gladfelter, W. L. J. Am. Chem. Soc. 1991, 113, 1054.
7. Gargulak, J. D.; Hoffman, R. D.; Gladfelter, W. L. J. Mol. Catal. 1991, 68, 289.
8. Gargulak, J. D.; Berry, A. J.; Noirot, M. D.; Gladfelter, W. L. J. Am. Chem. Soc. 1992, 114, 8933.
9. Gargulak, J. D.; Gladfelter, W. L. Inorg. Chem. 1994, 33, 253.
10. Grate, J. H.; Hamm, D. R.; Valentine, D. H. U.S. Patent 4603216, 1986.
11. Grate, J. H.; Hamm, D. R.; Valentine, D. H. U.S. Patent 4629804, 1986.
12. Grate, J. H.; Hamm, D. R.; Valentine, D. H. U.S. Patent 4705883, 1987.
13. Ragaini, F.; Cenini, S.; Demartin, F. J. Chem. Soc., Chem. Commun. 1992, 1467.
14. Ragaini, F.; Cenini, S.; Demartin, F. Organometallics 1994, 13, 1178.
15. Braunstein, P.; Bender, R.; Kervennal, J. Oganometallics 1982, 1, 1236.
16. Ugo, R.; Psaro, R.; Pizzotti, M.; Nardi, P.; Dossi, C.; Andreetta, A.; Capparella, G. J. Organomet. Chem. 1991, 417, 211.
17. Valli, V. L. K.; Alper, H. J. Am. Chem. Soc. 1993, 115, 3778.
18. Leconte, P.; Metz, F.; Mortreux, A.; Osborn, J. A.; Paul, F.; Petit, F.; Pillot, A. J. Chem. Soc., Chem. Commun. 1990, 1616.
19. Cenini, S.; Ragaini, F.; Pizzotti, M.; Porta, F.; Mestroni, G.; Alessio, E. J. Mol. Catal. 1991, 64, 179.
20. Wehman, P.; Dol, G. C.; Moorman, E. R.; Kramer, P. C. J.; van Leeuwen, P. W. N. M.; Fraanje, F.; Goubitz, K. Organometallics 1994, 13, 4856.
21. Berman, R. S.; Kochi, J. K. Inorg. Chem. 1980, 19, 248.
22. Skoog, S. J.; Campbell, J. P.; Gladfelter, W. L. Organometallics 1994, 13, 4137.
23. Liebeskind, L. S.; Sharpless, K. B.; Wilson, R. D.; Ibers, J. A. J. Am. Chem. Soc. 1978, 100, 7061.
24. Pizzotti, M.; Porta, F.; Cenini, S.; Demartin, F.; Masciocchi, N. J. Organomet. Chem. 1987, 330, 265.
25. Brouwer, E. B.; Ledzdins, P.; Rettig, S. J.; Ross, K. J. Organometallics 1994, 13, 2088.
26. Ridouane, F.; Sanchez, J.; Arzoumanian, H.; Pierrot, M. Acta Crystallogr. 1990, C46, 1407.
27. Barrow, M. J.; Mills, O. S. J. Chem. Soc. A 1971, 864.
28. Stella, S.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. J. Chem. Soc., Dalton Trans. 1988, 545.
29. Calligaris, M.; Yoshida, T.; Otsuka, S. Inorg. Chim. Acta 1974, 11, L15.
30. Sharp, P. R.; Hoard, W. D.; Barnes, C. L. J. Am. Chem. Soc. 1990, 112, 2024.
31. Ang, H. G.; Kwik, W. L.; Ong, K. K. J. Fluorine Chem. 1993, 60, 43.
32. Kochi, J. K. Agnew.Chem., Int. Ed. Engl. 1988, 27, 1227.
33. Eberson, L. Adv. Phys. Org. Chem. 1982, 18, 79.
34. Eberson, L. Electron Transfer Reactions in Organic Chemistry; Springer-Verlag: Berlin, 1987.
35. Burger, B. J.; Bercaw, J. E. In Experimental Organometallic Chemistry; Wayda, A. L., Darensbourg, M. Y., Eds.; American Chemical Society: Washington, DC, 1987; Vol. 357, pp 79-98.
36. Sanchez-Delgado, R. A.; Bradley, J. S.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1976, 399.
37. Skoog, S. J.; Jorgenson, A. L.; Campbell, J. P.; Gladfelter, W. L.; Douskey, M.; Munson, E. J. Organomet. Chem. 1997. In press.
38. Galbraith, H. W.; Degering, F. E.; Hitch, F. E. J. Am. Chem. Soc. 1951, 73, 1323.
39. Wheeler, O. H.; Gonzalez, D. Tetrahedron 1964, 20, 189.
40. Smith, L. I.; Denyes, R. O. J. Am. Chem. Soc. 1936, 58, 304.
41. Newton, A. J. Am. Chem. Soc. 1943, 65, 2434.
42. Gasné, R. R.; Koval, C. A.; Lisensky, G. C. Inorg. Chem. 1980, 19, 2854.
43. Geiser, W. E. In Organometallic Radical Processes; Trogler, W. C., Ed.; Elsevier: Amsterdam, 1990; pp 142-172.
44. Geiger, W. E. Prog. Inorg. Chem. 1985, 33, 275.
45. Adams, R. A. Electrochemistry at Solid Electrodes; Marcel Dekker: New York, 1969; (a) p 221, (b) p 126.
46. TEXSAN 5.0, Molecular Structure Corporation: The Woodlands, TX.
47. Cromer, D. T.; Waber, J. T. In International Tables for X-Ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol. IV, Table 2.2A.
48. Cromer, D. T. In International Tables for X-Ray Crystallography, Kynoch Press: Birmingham, England, 1974; Vol. IV, Table 2.3.1.
49. Giguère, P. A.; Liu, I. D. Can. J. Chem. 1952, 30, 948.
50. Maki, A. H.; Geske, D. H. J. Am. Chem. Soc. 1961, 83, 1852.
51. Holleck, L.; Becher, D. J. Electroanal. Chem. 1962, 4, 321.
52. Geer, R. D.; Byker, H. J. J. Org. Chem. 1982, 47, 1662.
53. Zuman, P. Substituent Effects in Organic Polarography; Plenum Press: New York, 1967.
54. Geske, D. H.; Ragle, J. L.; Bambenek, M. A.; Balch, A. L. J. Am. Chem. Soc. 1964, 86; 987.
55. Bard, A. J.; Faulkner, L. R. Electrochemical Methods; John Wiley & Sons: New York, 1980; (a) p 218, (b) p 200.
56. 1 = 5.4 Å).
57. Nadjo, L.; Savéant, J. M. J. Electroanal. Chem. 1973, 48, 113.
58. Nicholson, R. S.; Shain, I. Anal. Chem. 1964, 36, 706.
59. Klingler, R. J.; Kochi, J. K. J. Phys. Chem. 1981, 85, 1731.
60. Klingler, R. J.; Kochi, J. K. J. Am. Chem. Soc. 1980, 102, 4790.
61. Skoog, S. J.; Tabakovic, I.; Gladfelter, W. L. Inorg. Chem. 1997. Submitted for publication.
62. Kochi, J. K. In Organometallic Radical Processes; Trogler, W. C., Ed.; Elsevier: Amsterdam, 1990; pp 201-269.
63. Vasapollo, G.; Nobile, C. F.; Giannoccaro, P.; Allegretta, F. J. Organomet. Chem. 1984, 277, 417.
64. Reichardt, C. Angew. Chem., Int. Ed. Engl. 1965, 4, 29.
65. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper and Row: New York, 1987.
66. Kosower, E. M.; Mohammad, M. J. Am. Chem. Soc. 1968, 90, 3271.
67. Sherlock, S. J.; Boyd, D. C.; Moasser, B.; Gladfelter, W. L. Inorg. Chem. 1991, 30, 3626.
68. Alper, H.; Edward, J. T. Can. J. Chem. 1970, 48, 1543.
69. Shen, J. K.; Shi, Y. L.; Gao, Y. C.; Shi, Q. Z.; Basolo, F. J. Am. Chem. Soc. 1988, 110, 2414.
70. Shen, J. K.; Gao, Y. C.; Basolo, F. Organometallics 1989, 8, 2144.
71. Scandola, F.; Balzani, V.; Schuster, G. B. J. Am. Chem. Soc. 1981, 103, 2519.
72. -1.
73. -1.
74. Marcus, R. A. Annu. Rev. Phys. Chem. 1964, 15, 155.
75. Marcus, R. A. J. Chem. Phys. 1968, 72, 891.
76. Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265.
77. Schlesener, C. J.; Amatore, C.; Kochi, J. K. J. Am. Chem. Soc. 1984, 106, 3567
78. p.
79. This value of the intrinsic barrier ΔG‡(0) represents a minimum value, which assumes solvent reorganization only. This minimum value of ΔG‡(0) would provide the fastest rate possible for the outer-sphere treatment (see ref 34 pp 48-49).
80. Savéant, J.-M. Adv. Phys. Org. Chem. 1990, 26, 1.
81. Lewis, E. S. J. Am. Chem. Soc. 1989, 111, 7576.
82. Wong, C. L.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 5593.
83. Fukuzumi, S.; Wong, C. L.; Kochi, J. K. J. Am. Chem. Soc. 1980, 102, 2928.
84. Lund, T.; Lund, H. Acta Chem. Scand. Ser. B 1986, 40, 470.
85. Lexa, D.; Saveant., J-M.; Su, K.-B.; Wang, D.-L. J. Am. Chem. Soc. 1988, 110, 7617.
86. Halpern, J. Quart. Rev. 1961, 15, 207.
87. Cohen, A. O.; Marcus, R. A. J. Phys. Chem. 1968, 72, 4249.
88. Lee, K.-W.; Brown, T. L. J. Am. Chem. Soc. 1987, 109, 3269.
89. Burke, M. R.; Brown, T. L. J. Am. Chem. Soc. 1989, 111, 5185.
90. Pross, A. Acc. Chem. Res. 1985, 18, 212.
91. Sandrini, D.; Gandolfi, M. T.; Maestri, M.; Bolletta, F.; Balzani, V. Inorg. Chem. 1984, 23, 3017.
92. Cannon, R. D. Electron Transfer Reactions; Butterworths: London, 1980.
93. -1). For an excellent treatment and application of the linearized form of the Marcus equation to an outer-sphere electron transfer, see eq 13 in ref 83 and ref 32 p 1230.
94. Eberson, L.; Shaik, S. J. Am. Chem. Soc. 1990, 112, 4489.
95. Jagannadham, V.; Steenken, S. J. Am. Chem. Soc. 1988, 110, 2188.
96. Steenken, S. Top. Curr. Chem. 1996, 177, 125.
97. Cenini, S.; Porta, R.; Pizzotti, F.; Crotti, C. J. Chem. Soc., Dalton Trans. 1985, 163.