Titanocene borane σ-complexes

Journal of the American Chemical Society

Volumn 121, Issue 21, 1999, Pages 5033-5046

  Muhoro, Clare N ^a   He, Xiaoming ^a   Hartwig, John F ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; TITANOCENE BISBORANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONCENTRATION RESPONSE; CRYSTALLOGRAPHY; ENTROPY; GEOMETRY; MODEL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION TIME; REDUCTION; SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033516333     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9900757     Document Type: Article

References (76)

1. Crabtree, R. H. Angew. Chem., Int. Ed. Engl. 1993, 32, 789.
2. Heinekey, D. M.; Oldham, W. J. Chem. Rev. 1993, 93, 913.
3. Schubert, U. Adv. Organomet. Chem. 1990, 30, 151.
4. For a review of transition metal alkane complexes see: Hall, C.; Perutz, R. N. Chem. Rev. 1996, 96, 3125.
5. Brown, C. E.; Ishikawa, Y.-I.; Hackett, P. A.; Rayner, D. M. J. Am. Chem. Soc. 1990, 112, 2530.
6. Turner, J. J.; Burdett, J. K.; Perutz, R. N.; Poliakoff, M. Pure Appl. Chem. 1977, 49, 271.
7. Rest, A. J.; Whitwell, I.; Graham, W. A. G.; Hoyano, J. K.; McMaster, A. D. J. Chem. Soc. 1987, 1181.
8. Geftakis, S.; Ball, G. E. J. Am. Chem. Soc. 1998, 120, 9953.
9. Buchanan, J. M.; Stryker, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 1537-1550.
10. Gould, G. L.; Heinekey, D. M. J. Am. Chem. Soc. 1989, 111, 5502.
11. Bullock, R. M.; Headford, C. E. L.; Hennessy, K. M.; Kegley, S. E.; Norton, J. R. J. Am. Chem. Soc. 1989, 111, 3897.
12. Bullock, R. M. In Transition Metal Hydrides, Dedieu, A., Ed.; VCH: New York, 1992; p 263.
13. Evans, D. R.; Drovetskaya, T.; Bau, R.; Reed, C. A.; Boyd, P. D. W. J. Am. Chem. Soc. 1997, 119, 3633.
14. Brookhart, M.; Green, M. L. H.; Wong, L.-L. Prog. Inorg. Chem. 1988, 36, 1-124.
15. Halpern, J. Science 1982, 217, 401.
16. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, 2nd ed.; University Science Books: Mill Valley, CA, 1987.
17. Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1965, 87, 16.
18. Sommer, L. H.; Lyons, J. E.; Fujimoto, H. J. Am. Chem. Soc. 1969, 91, 2670.
19. Crabtree, R. H. Chem. Rev. 1995, 95, 987.
20. Hill, C. L. Activation and Functionalization of Alkanes; John Wiley and Sons: New York, 1989.
21. Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Petersen, T. H. Acc. Chem. Res. 1995, 28, 154.
22. Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
23. For a discussion on experiments using isotope effects to determine the intermediacy of alkane complexes in C-H activation see: Bullock, R. M. In Transition Metal Hydrides; Dedieu, A., Ed.; VCH: New York, 1992; pp 263-307.
24. 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.
25. Zeigler, T.; Folga, E. J. Am. Chem. Soc. 1993, 115, 636.
26. Brintzinger, H.; Beck, S.; Leclerc, M.; Stehling, U.; Roll, W. Stud. Surf. Sci. Catal. 1994, 89, 193.
27. Clawson, L.; Soto, J.; Buchwald, S. L.; Steigerwald, M. L.; Grubbs, R. H. J. Am. Chem. Soc. 1985, 107, 3377.
28. Cotter, W. D.; Bercaw, J. E. J. Organomet. Chem. 1991, 417, C1.
29. Grubbs, R. H.; Coates, G. W. Acc. Chem. Res. 1996, 29, 85.
30. Leclerc, M. K.; Brintzinger, H. H. J. Am. Chem. Soc. 1995, 117, 1651.
31. Piers, W. E.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 9406.
32. He, X.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 1696.
33. Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957.
34. Dorigo, A. E.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 115.
35. Westcott, S. A.; Blom, H. P.; Marder, T. B.; Baker, R. T. J. Am. Chem. Soc. 1992, 114, 8863.
36. Evans, D. A.; Fu, G.; Anderson, B. A. J. Am. Chem. Soc. 1992, 114, 6679.
37. Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350.
38. Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179.
39. Hartwig, J. F.; Muhoro, C. N.; He, X.; Eisenstein, O.; Bosque, R.; Maseras, F. J. Am. Chem. Soc. 1996, 118, 10936.
40. Muhoro, C. N.; Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1997, 36, 1510.
41. Hartwig, J. F.; DeGala, S. R. J. Am. Chem. Soc. 1994, 116, 3661.
42. Lantero, D. R.; Motry, D. H.; Ward, D. L.; Smith, M. R. J. Am. Chem. Soc. 1994, 116, 10811.
43. Lauher, J. W.; Hoffmann, R. J. Am. Chem. Soc. 1976, 98, 1729.
44. Spaltenstein, E.; Palma, P.; Kreutzer, K. A.; Willoughby C. A.; Davis, W. M.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 10308.
45. 3) is unstable in the absence of added silane, excess silane was added to the sample before addition of borane.
46. Hartwig, J. F.; He, X. Angew. Chem., Int. Ed. Engl. 1996, 35, 315.
47. 2 of 2.439-2.483 Å.
48. Miao, F. M.; Prout, K. Cryst. Struct. Commun. 1982, 11, 269.
49. Prout, K.; Cameron, T. S.; Forder, R. A.; Critchley, S. R.; Denton, B.; Rees, G. V. Acta Crystallogr., B 1974, 30, 2290.
50. McCamley, A.; Miller, T. J. Acta Crystallogr., C 1994, 50, 33.
51. Labella, L.; Chernega, A.; Green, M. L. H. J. Organomet. Chem. 1995, C18, 485.
52. Pattasina, J. W.; Heeres, H. J.; van Boulhuis, F.; Meetsma, A.; Teuben, J. H. Organometallics 1987, 6, 1004.
53. Nöth, H.; Wrackmeyer, B. Nuclear Magnetic Resonance Spectroscopy of Boron Compounds, 1st ed.; Springer-Verlag: New York, 1978; p 460.
54. Goetze, R.; Nöth, H.; Pommerening, H.; Sedlak, D.; Wrackmeyer, B. Chem. Ber. 1981, 114, 1884.
55. The electronic properties of the borane can be systematically perturbed by changing the identity of the substituent on the aromatic ring of the catecholborane. Hammett substituent constants for the respective benzoic acids were used to estimate the electronic properties of the boranes, bearing in mind that the substituents have different σ parameters when located in the metal and para positions. The electrophilicity of the boranes should decrease in the trend HBcat-4-Cl > HBcat-4-SMe > HBcat > HBcat-4-Me. Connors, K. A. Chemical Kinetics: the study of reaction rates in solution, 1st ed.; VCH: New York, 1990; p 480.
56. Hartwig, J. F.; Huber, S. J. Am. Chem. Soc. 1993, 115, 4908.
57. Kaez, H. D.; Fellmann, W.; Wilkes, G. R.; Dahl, L. F. J. Am. Chem. Soc. 1965, 87, 2755.
58. Andersen, E. L.; Felhner, T. P. J. Am. Chem. Soc. 1978, 100, 4606.
59. Marks, T. J.; Kolb, J. R. Chem. Rev. 1977, 77, 263.
60. Brookhart, M.; Green, M. L. H. J. Organomet. Chem. 1983, 250, 395.
61. Binger, P.; Sandmeyer, F.; Krüger, C.; Kuhnigk, J.; Goddard, R.; Erker, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 197.
62. Bercaw, J. E.; Brintzinger, H. H. J. Am. Chem. Soc. 1972, 94, 1219.
63. Bennet, J. L.; Wolczanski, P. T. J. Am. Chem. Soc. 1994, 116, 2179.
64. Davies, N.; James, B. D.; Wallbridge, M. G. H. J. Chem. Soc. A 1969, 2601.
65. Palmer, G. T.; Basolo, F.; Kool, L. B.; Rausch, M. D. J. Am. Chem. Soc. 1986, 108, 4417.
66. For an early example with monocyclopentadienyl compounds see: Schuster-Woldan, H. G.; Basolo, F. J. Am. Chem. Soc. 1966, 88, 1657.
67. 3 cyclopentadienyl complex is less consistent with the large positive entropy of activation and steric effects described below.
68. Atwood, J. D. Inorganic and Organometallic Reaction Mechanisms; Cole Publishing Co.; Monterey, CA, 1985; p 17.
69. Rablen, P. R.; Hartwig, J. F.; Nolan, S. P. J. Am. Chem. Soc. 1994, 116, 4121.
70. Kool, L. B.; Rausch, M. D.; Alt, H. G.; Herberhold, M.; Thewalt, U.; Wolf, B. Angew. Chem., Int. Ed. Engl. 1985, 24, 394.
71. Erskine, G. H.; Wilson, D. A.; McCowan, J. D. J. Organomet. Chem. 1976, 114, 119.
72. Shur, V. B.; Burlakov, V. V.; Vol'pin, M. E. J. Organomet. Chem. 1988 347, 77.
73. Kabalka, G. W.; Reddy, N. K.; Narayana, C. Tetrahedron Lett. 1992, 33, 865.
74. Cooksey, C., J.; Land, E. J.; Riley, P. A. Org. Prep. Proced. Int. 1996, 28, 463.
75. Männig, D.; Nöth, H. J. Chem. Soc., Dalton Trans. 1985, 1689.
76. Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1971, 93, 1816.