Activation of C-H Bonds in Saturated Hydrocarbons on Photolysis of (η5-C5Me5)(PMe3)IrH2. Relative Rates of Reaction of the Intermediate with Different Types of C-H Bonds and Functionalization of the Metal-Bound Alkyl Groups

Journal of the American Chemical Society

Volumn 105, Issue 12, 1983, Pages 3929-3939

  Janowicz, Andrew H ^a   Bergman, Robert G ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBONS - CATALYSIS;

ORGANOMETALLICS;

EID: 0020766699     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00350a031     Document Type: Article

References (86)

1. Parshall, G. W. Catalysis (London) 1977, 1, 335.
2. Shilov A. E.; Shteinman, A. A. Coord. Chem. Rev. 1977, 24, 97.
3. Webster, D. E. Adv. Organomet. Chem. 1977, 15, 147.
4. Parshall, G. W. “Homogeneous Catalysis” Wiley-Interscience: New York, 1980; p 179 ff.
5. Coliman J. P.; Hegedus, L. S. “Principles and Applications of Organotransition Metal Chemistry” University Science Books: Mill Valley, CA, 1980, p 222 ff.
6. Halpern, J. Discuss. Faraday Soc. 1968, 46, 7.
7. Walling, C. “Free Radicals in Solution” Wiley: New York, 1957.
8. Huyser, E. S. “Free Radical Chain Reactions” Wiley: New York, 1970.
9. Pryor, W. A. “Free Radicals” McGraw-Hill: New York, 1966.
10. Beckwith, A. L. J.; Duong, T. J. Chem. Soc. Chem. Commun. 1978, 413.
11. Cohen Z.; Keinan E.; Mazur Y.; Haim Varkony T. J. Org. Chem. 1975, 40, 2141 and references cited there
12. Deno, N. C.; Jedziniak E. J.; Messer L. A.; Meyer M. D.; Stroud S. G.; Tomezsko, E. S. Tetrahedron 1977, 33, 2503.
13. Rozen S.; Gal C; Faust Y. J. Am. Chem. Soc. 1980, 102, 6861 and references cited there
14. Olah G. A.; Parker D. G.; Yoneda, N. Angew. Chem., Int. Ed. Engl. 1978, 17, 909.
15. Gol'dshleger, N. F.; Tyabin M. B.; Shilov A. E.; Shteinman, A. A. Zh. Fiz. Khim. 1969, 43, 2174.
16. Hodges R. J.; Webster D. E.; Wells P. B. J. Chem. Soc, Chem. Commun. 1971, 462.
17. Kochi, J. K. In “Free Radicals” Kochi J. K., Ed.; Wiley-Inter-science: 1973; Vol. II, Chapter 11.
18. Howard, J. A. In “Free Radicals” Kochi, J. K. Ed., Wiley-Interscience: New York, 1973; Vol. II, Chapter 12.
19. Groves, J. T. Adv. Inorg. Biochem. 1979, 1, 119.
20. Groves J. T.; Nemo T. E.; Myers R. S. J. Am. Chem. Soc. 1979, 101, 1032.
21. Groves J. T.; Van Der Puy, M. J. Am. Chem. Soc. 1976, 98, 5290.
22. Chang C. K.; Kuo, M.-S. J. Am. Chem. Soc. 1979, 101, 3413.
23. Groves J. T.; Kruper W. J. Jr., J. Am. Chem. Soc. 1979, 101, 7613.
24. Hill C. L.; Schardt B. C. J. Am. Chem. Soc. 1980, 102, 637.
25. Sofranko J. A.; Eisenberg R.; Kampmeier J. A. J. Am. Chem. Soc. 1980, 102, 1163.
26. For examples, see: (a) Foley, P.; Whitesides G. M. J. Am. Chem. Soc. 1979, 101, 2732.
27. Clark, H. C.; Geol A. B.; Geol S. Inorg. Chem. 1979, 188, 2803.
28. Simpson S. J.; Turner H. W.; Andersen R. A. J. Am. Chem. Soc. 1979, 101, 7728.
29. Empsall H. D.; Hyde E. M.; Markham R.; McDonald W. S.; Norton M.C.; Shaw B. L.; Weeks B. J. Chem. Soc, Chem. Commun. 1977, 589.
30. Al-Salem, N. A.; McDonald W. S.; Markham R.; Norton M.C.; Shaw, B. L. J. Chem. Soc, Dalton Trans 1980, 59 and references cited there
31. Andersen R. A.; Jones R. A.; Wilkinson, J. Chem. Soc, Dalton Trans. 1978, 446.
32. Simpson S. J.; Turner H. W.; Andersen R. A. Inorg. Chem. 1981, 20, 2991.
33. Chappell S. D.; Cole-Hamilton, D. J. Chem. Soc, Chem. Commun. 1980, 238.
34. Tulip T. H.; Thorn D. L. J. Am. Chem. Soc. 1981, 103, 2448.
35. Adams R. D.; Selegue J. P. Inorg. Chem. 1980, 19, 1795.
36. Werner H.; Werner R. J. Organomet. Chem. 1981, 209, C60.
37. Hale L. F.; Armentrout P. B.; Beauchamp J. L. J. Am. Chem. Soc. 1981, 103, 962.
38. Allison J.; Feas R. B.; Ridge D. P. J. Am. Chem. Soc. 1979, 101, 1332.
39. Ozin G. A.; McIntosh D. F.; Mitchell, S. A. 1981, 102, 1574.
40. Breckenridge W. H.; Renlund, A. M. J. Phys. Chem. 1679, 83, 303.
41. Remick R. J.; Asunta T. A.; Skell, P. S. J. Am. Chem. Soc 1979, 101, 1320.
42. Parshall, G. W. Acc. Chem. Res. 1975, 8, 113.
43. Berry M.; Elmitt K.; Green M.L.H. J. Chem. Soc, Dalton Trans. 1979, 1950.
44. Green, M. L. H.; Berry M.; Couldwell C; Prout, K. Nouv. J. Chim. 1977, 1, 187.
45. Berry M.; Elmitt K.; Green M.L.H. J. Chem. Soc, Dalton Trans. 1971, 1508.
46. Ittel S. D.; Tolman C. A.; Krusic P. J.; English A. D.; Jesson J. P. Inorg. Chem. 1978, 17, 3432.
47. Ittel S. D.; Tolman C. A.; English A. D.; Jesson, J. P. J. Am. Chem. Soc 1976, 98, 6073; 1978, 100, 7577.
48. Bradley M. G.; Roberts D. A.; Geoffroy, G. L. J. Am. Chem. Soc 1981, 103, 379.
49. Rausch M. D.; Gastinger R. G.; Gardner S. A.; Brown R. K.; Wood, J. S. J. Am. Chem. Soc 1977, 99, 7870.
50. Crabtree R. H.; Mihelcic J. M.; Quirk J. M. J. Am. Chem. Soc. 1979, 101, 7738.
51. Crabtee R. H.; Mellea M. F.; Mihelcic J. M.; Quirk J. M. J. Am. Chem. Soc. 1982, 104, 107.
52. Crabtree R. H.; Demou P.C.; Eden D.; Mihelcic; J. M.; Parnell C. A.; Quirk J. M.; Morris G. E. J. Am. Chem. Soc. 1982, 104, 6994.
53. Baudry D.; Ephritikine M.; Felkin H. J. Chem. Soc, Chem. Commun. 1980, 1243.
54. Baudry D.; Ephritikhine M.; Felkin H.; Za-krzewski, J. J. Chem. Soc, Chem. Commun. 1982, 1235.
55. Janowicz A. H.; Bergman R. G. J. Am. Chem. Soc. 1982, 104, 352.
56. Kang J. W.; Moseley K.; Maitlis P. M. J. Am. Chem. Soc. 1969, 91, 5970.
57. Geoffrey G. L.; Wrighton, M. S. “Organometallic Photochemistry” Academic Press: New York, 1979.
58. Pierantozzi R.; Geoffrey G. L. Inorg. Chem. 1980, 19, 1821 and references cited there.
59. Following submission of the preliminary communication, an alternative preparation of complex 5 was reported: Isobe, K.; Bailey P. M.; Maitlis P. M. J. Chem. Soc, Dalton Trans. 1981, 2003.
60. Although this system seems to avoid it, intramolecular C-H activation in coordinated Me3P ligands is known; see, for example: (a) Chiu, K. W.; Wong, W.-K.; Wilkinson G. J. Chem. Soc, Chem. Commun. 1981, 451.
61. Rathke J. W.; Muetterties E. L. J. Am. Chem. Soc. 1975, 97, 3272.
62. A1-Jibori, S.; Crocker C; McDonald W. S.; Shaw B. L. J. Chem. Soc, Dalton Trans. 1981, 1572 and references cited there.
63. See, for example: (a) Labinger, J. A.; Braus R. J.; Dolphin D.; Osborn, J. A. J. Chem. Soc, Chem. Comm. 1970, 612.
64. Jensen F. R.; Knickel B. J. Am. Chem. Soc. 1971, 93, 6339.
65. Pearson R. G.; Muir W. R. J. Am. Chem. Soc. 1970, 92, 5519.
66. Lau, K. S. Y.; Fries R. W.; Stille J. K. J. Am. Chem. Soc. 1974, 96, 4983.
67. Labinger J. A.; Osborn J. A. Inorg. Chem. 1980, 198, 3230.
68. Pryor W. A.; Tang F. Y.; Tang R. H.; Church D. F. J. Am. Chem. Soc. 1982, 104, 2885 and references cited there.
69. Baghal-Vayjooee, M. H.; Benson S. W. J. Am. Chem. Soc. 1979, 101, 2838.
70. Bergman, R. G. Acc. Chem. Res. 1980, 13, 113.
71. Chock P. B.; Halpern J. J. Am. Chem. Soc. 1966, 88, 3511.
72. Kitaura K.; Obara S.; Morokuma, K. J. Am. Chem. Soc, 1981, 103, 2891. See also
73. Noell J. O.; Hay, P. J. J. Am. Chem. Soc 1982, 104, 4578.
74. Abis L.; Sen A.; Halpern J. J. Am. Chem. Soc. 1978, 100, 2915.
75. Mays M. J.; Simpson R. N. F.; Stefanini F. P. J. Chem. Soc. A 1970, 3000.
76. Howarth O. W.; McAteer C. H.; Moore P.; Morris G. E. J. Chem. Soc, Chem. Commun. 1982, 745.
77. Schwartz J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
78. Hoyano J. K.; Graham W.A.G. J. Am. Chem. Soc. 1982, 104, 3723.
79. Jensen F. R.; Rickbom, B. “Electrophilic Substitution of Organ0-mercurials” McGraw-Hill: New York, 1968.
80. Makarova L. G.; Nesmeyanov, A. N. The Organic Compounds of Mercury; North-Holland Publishing Co.: Amsterdam, 1967.
81. See, for example: Page, M. I.; Jencks, W. P. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 1678.
82. For an excellent discussion of the factors which control the relative rates of chemically similar intra- and intermolecular reactions, see: Illuminati G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.
83. Bercaw J. E.; Erwin D. K., private communication. Erwin, D. K. Ph. D. Thesis, California Institute of Technology, 1979.
84. Evidence that the corresponding rhodium system will also insert into the C-H bonds of saturated hydrocarbons has been obtained recently: (a) Jones W. D.; Feher, F. J. Organometallics 1983, 2, 562.
85. Periana-Pillai, R. A.; Bergman R. G., unpublished results.
86. Booth B. L.; Haszeldine R. N.; Hill M. J. Organomet. Chem. 1969, 16, 491.