Modeling the proposed intermediate in alkane carbon-hydrogen bond activation by Cp*(PMe3)Ir(Me)OTf: Synthesis and stability of novel organometallic iridium(V) complexes

Organometallics

Volumn 18, Issue 14, 1999, Pages 2707-2717

  Alaimo, Peter J ^a   Bergman, Robert G ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001203328     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990255p     Document Type: Article

References (89)

1. For recent reviews of C-H activation, see refs 2-5.
2. Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154-162 and references therein.
3. Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879-2932 and references therein.
4. Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 2181 and references therein.
5. Sen, A. New Approaches in C-H Activation of Alkanes. In Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Two Volumes; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: New York, 1996; Vol. 2, pp 1081-1092.
6. Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462-10463.
7. Arndtsen, B. A.; Bergman, R. G. Science 1995, 270, 1970-1973.
8. Arndtsen, B. A.; Bergman, R. G. J. Organomet. Chem. 1995, 504, 143-146.
9. Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517-2518.
10. Luecke, H. F.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 11538-11539.
11. Alaimo, P. J.; Arndtsen, B. A.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 5269-5270.
12. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; pp 279-353.
13. Gutiérrez-Puebla, E.; Monge, Á.; Nicasio, M. C.; Pérez, P. J.; Poveda, M. L.; Carmona, E. Chem. Eur. J. 1998, 4, 2225-2236.
14. Andreucci, L.; Diversi, P.; Ingrosso, G.; Lucherini, A.; Marchetti, F.; Adovasio, V.; Nardelli, M. J. Chem. Soc., Dalton Trans. 1986, 477-487.
15. Gómez, M.; Robinson, D. J.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1983, 825-826.
16. Ferrari, A.; Polo, E.; Rüegger, H.; Sostero, S.; Venanzi, L. M. Inorg. Chem. 1996, 35, 1602-1608.
17. Gómez, M.; Kisenyi, J. M.; Sunley, G. J.; Maitlis, P. M. J. Organomet. Chem. 1985, 296, 197-207.
18. Hay-Motherwell, R. S.; Wilkinson, G.; Hussain-Bates, B.; Hursthouse, M. B. Polyhedron 1993, 72, 2009-2012.
19. Hay-Motherwell, R. S.; Wilkinson, G.; Hussain-Bates, B.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1992, 3477-3482.
20. Paneque, M.; Poveda, M. L.; Taboada, S. J. Am. Chem. Soc. 1994, 116, 4519-4520.
21. Gutiérrez-Puebla, E.; Monge, Á.; Paneque, M.; Poveda, M. L.; Taboada, S.; Trujillo, M.; Carmona, E. J. Am. Chem. Soc. 1999, 121, 346-354.
22. Gilbert, T. M.; Hollander, F. J.; Bergman, R. G. J. Am. Chem. Soc. 1985, 107, 3508-3516.
23. Gilbert, T. M.; Bergman, R. G. Organometallics 1983, 2, 1458-1460.
24. Fernandez, M.-J.; Maitlis, P. M. Organometallics 1983, 2, 164-165.
25. Fernandez, M.-J.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1984, 2063-2066.
26. Ruiz, J.; Spencer, C. M.; Mann, B. E.; Taylor, B. F.; Maitlis, P. M. J. Organomet. Chem. 1987, 325, 253-260.
27. Isobe, K.; Bailey, P. M.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1981, 808-809.
28. Isobe, K.; Miguel, A. V. d.; Nutton, A.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1984, 929-933.
29. 3, P(H)(Ph)(n-decyl)).
30. Heinekey, D. M.; Payne, N. G.; Schulte, G. K. J. Am. Chem. Soc. 1988, 110, 2303-2305.
31. Gilbert, T. M.; Bergman, R. G. J. Am. Chem. Soc. 1985, 107, 3502-3507.
32. Watson, P. L. J. Am. Chem. Soc. 1983, 105, 6491-6493.
33. Thompson, M. E.; Baxter, S. M.; Bulls, A. R.; Burger, B. J.; Nolan, M. C.; Santarsiero, B. D.; Schaefer, W. P.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 203-219.
34. 0 metal center.
35. Strout, D. L.; Zarić, S.; Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1996, 118, 6068-6069.
36. Su, M.-D.; Chu, S.-Y. J. Am. Chem. Soc. 1997, 119, 5373-5383.
37. Burger, P.; Arndtsen, B. A.; Luecke, H. F.; Bergman, R. G. Unpublished results.
38. See ref 12, p 330.
39. Balch, A. L.; Catalano, V. J.; Chatfield, M. A.; Nagle, J. K.; Olmstead, M. M.; Reedy, P. E. J. Am. Chem. Soc. 1991, 113, 1252-1258 (dpma = bis((diphenylphosphino)methyl)phenylarsine).
40. Werner, H.; Ortmann, D. A.; Gevert, O. Chem. Ber. 1996, 129, 411-417.
41. Courtneidge, J. L.; Davies, A. G.; Shields, C. J.; Yazdi, S. N. J. Chem. Soc. Perkin Trans. 2 1988, 799-805.
42. Cotton, F. A.; Matusz, M. Inorg. Chim. Acta 1987, 131, 213-216.
43. Chakravarty, A. R.; Cotton, F. A.; Tocher, D. A. Acta Crystallogr. 1985, C41, 698-699.
44. Hoffman, P. R.; Caulton, K. G. J. Am. Chem. Soc. 1975, 97, 4221-4228.
45. La Placa, S. J.; Ibers, J. A. Inorg. Chem. 1965, 4, 778-783.
46. For leading references, see refs 47 and 48.
47. Pregosin, P. S.; Kunz, R. Helv. Chim. Acta 1975, 58, 423-431.
48. Redfield, D. A.; Nelson, J. H.; Cary, L. W. Inorg. Nucl. Chem. Lett. 1974, 10, 727-733.
49. 3 carbon centers, see refs 50-64.
50. 3 carbon atoms. For leading references, see ref 12.
51. From Au(III): Tamaki, A.; Magennis, S. A.; Kochi, J. K. J. Am. Chem. Soc. 1974, 96, 6140-6148.
52. From Au(III): Komiya, S.; Albright, T. A.; Hoffmann, R.; Kochi, J. K. J. Am. Chem. Soc. 1976, 98, 7255-7265.
53. From Ni(II): Yamamoto, T.; Abla, M. J. Organomet. Chem. 1997, 535, 209-211
54. From Pd(II): Moravskiy, A.; Stille, J. K. J. Am. Chem. Soc. 1981, 103, 4182-4186.
55. From Pd(II): Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933-4941.
56. From Pd(II): Ito, T.; Tsuchiya, H.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1977, 50, 1319-1327.
57. From Pd(FV): Markies, B. A.; Canty, A. J.; Boersma, J.; van Koten, G. Organometallics 1994, 13, 2053-2058.
58. From Pd(IV): Byers, P. K.; Canty, A. J.; Crespo, M.; Puddephatt, R. J.; Scott, J. D. Organometallics 1988, 7, 1363-1367.
59. From Pt(II): DiCosimo, R.; Whitesides, G. M. J. Am. Chem. Soc. 1982, 104, 3601-3607.
60. From Pt(II): Foley, P.; DiCosimo, R.; Whitesides, G. M. J. Am. Chem. Soc. 1980, 102, 6713-6725.
61. From Pt(IV): Goldberg, K. I.; Yan, J.; Winter, E. L. J. Am. Chem. Soc. 1994, 116, 1573-1574.
62. From Pt(IV): Goldberg, K. I.; Yang, J.; Breitung, E. M. J. Am. Chem. Soc. 1995, 117, 6889-6896.
63. (a) From Pt(IV): Hill, G. S.; Puddephatt, R. J. Organometallics 1997, 16, 4522-4524.
64. (b) Hill, G. S.; Yap, G. P. A.; Puddephatt, P. J. Organometallics 1999, 18, 1408-1418.
65. From Pt(IV): Brown, M. P.; Puddephatt, R. J.; Upton, C. E. E. J. Chem. Soc., Dalton Trans. 1974, 2457-2465.
66. Theoreticians have rationalized the relative difficulty of C-C reductive elimination, compared to C-H or H-H reductive elimination: Low, J. J.; Goddard, W. A. J. Am. Chem. Soc. 1986, 108, 6115-6128.
67. Churchill, M. R.; Fettinger, J. C.; Janik, T. S.; Rees, W. M.; Thompson, J. S.; Tomaszewski, S.; Atwood, J. D. J. Organomet. Chem. 1987, 323, 233-246.
68. A reveiwer has commented that "all indications...indicate that such reductive eliminations require prior ligand dissociation to a 16-electron intermediate". We agree that, in some systems, prior ligand dissociation is required to effect reductive elimination, but this does not seem to be universally true (see, for example: Buchanan, J. M.; Stryker, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 1537). We therefore do not see a need to postulate its occurrence here, although we obviously cannot determine from our data whether Cp "slippage" occurs prior to the reductive elimination step.
69. Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 5508-5509.
70. Miller, F. D.; Sanner, R. D. Organometallics 1988, 7, 818-825.
71. Fachinetti, G.; Floriani, C. J. Chem. Soc., Chem. Commun. 1974, 516-517.
72. Werner, H.; Hofmann, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 794-795.
73. Paneque, M.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1989, 105-106.
74. Jones, W. D.; Kuykendall, V. L.; Selmeczy, A. D. Organometallies 1991, 10, 1577-1586.
75. Pedersen, A.; Tilset, M. Organometallics 1993, 12, 3064-3068.
76. Kubas, G. J.; Kiss, G.; Hoff, C. D. Organometallics 1991, 10, 2870-2876.
77. Ryan, O. B.; Tilset, M.; Parker, V. D. Organometallics 1991, 10, 298-304.
78. Jones, W. D.; Maguire, J. A. Organometallics 1985, 4, 951-953.
79. Crabtree, R. H. Angew. Chem., Int. Ed. Engl. 1993, 32, 789-805.
80. Barretta, A.; Cloke, F. G. N.; Feigenbaum, A.; Green, M. L. H.; Gourdon, A.; Prout, K. J. Chem. Soc., Chem. Commun. 1981, 156-158.
81. Crabtree, R. H.; Dion, R. P. J. Chem. Soc., Chem. Commun. 1984, 1260-1261.
82. Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222-7227.
83. Eilbracht, P.; Mayser, U. Chem. Ber. 1980, 113, 2211-2220.
84. Benfield, F. W. S.; Green, M. L. H. J. Chem. Soc., Dalton Trans. 1974, 1324-1331.
85. Elschenbroich, A. S. Organometallics, A Concise Introduction, 2nd ed.; VCH: New York, 1992; p 154.
86. For safety concerns, see ref 28.
87. XPREP, v. 5.03 (part of the SHELXTL Crystal Structure Determination Package); Siemens Industrial Automation, Inc., 1995.
88. Sheldrick, G. SADABS: Siemens Area Detector Absorption correction program; Siemens Industrial Automation, Inc., 1996.
89. teXsan: Crystal Structure Analysis Package; Molecular Structure Corp., 1985 and 1992.