M=Nα Cycloaddition and Nα-N β Insertion in the reactions of titanium hydrazido compounds with alkynes: A combined experimental and computational study

Journal of the American Chemical Society

Volumn 132, Issue 30, 2010, Pages 10484-10497

  Schofield, A Daniel ^a   Nova, Ainara ^b   Selby, Jonathan D ^a   Manley, Catherine D ^a   Schwarz, Andrew D ^a   Clot, Eric ^b   Mountford, Philip ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

[2 + 2] CYCLOADDITION; ACTIVATION PARAMETER; ARYL ALKYNES; ARYL GROUP; ATOM MIGRATION; COMPUTATIONAL STUDIES; DFT STUDY; DIAMIDES; ELECTRONWITHDRAWING; HAMMETT ANALYSIS; HYDRAZIDE LIGAND; IMIDO COMPOUNDS; INSERTION REACTIONS; REACTION CONSTANT; REACTION COORDINATES; REGIOCHEMISTRY; ROOM TEMPERATURE;

LIGANDS; TITANIUM;

ACETYLENE;

ALKYNE DERIVATIVE; TITANIUM DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CYCLOADDITION; ROOM TEMPERATURE; SUBSTITUTION REACTION;

EID: 77955035362     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1036513     Document Type: Article

References (96)

1. Johnson, B. F. G., Haymore, B. L., and Dilworth, J. D. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., and McCleverty, J. A., Eds.; Pergamon Press: Oxford, 1987; Vol. 2, p 100.
2. Nugent, W. A. and Mayer, J. M. Metal-Ligand Multiple Bonds; Wiley-Interscience: New York, 1988.
3. Mindiola, D. J. Angew. Chem., Int. Ed. 2008, 47, 1557
4. Fryzuk, M. D. Chem. Rec. 2003, 3, 2
5. MacKay, B. A. and Fryzuk, M. D. Chem. Rev. 2004, 104, 385
6. Kozak, C. M. and Mountford, P. Angew. Chem., Int. Ed. 2004, 43, 1186
7. Chatt, J., Pearman, A. J., and Richards, R. L. Nature 1975, 253, 39
8. Pickett, C. J. and Leigh, G. J. J. Chem. Soc., Chem. Commun. 1981, 1033
9. Hussain, W., Leigh, G. J., and Pickett, C. J. J. Chem. Soc., Chem. Commun. 1982, 747
10. Pickett, C. J. and Talamarin, J. Nature 1985, 317, 652
11. Yandulov, D. V. and Schrock, R. R. Science 2003, 76
12. Schrock, R. R. Acc. Chem. Res. 2005, 38, 955
13. Stephan, G. C., Sivasankar, C., Studt, F., and Tuczek, F. Chem.=Eur. J. 2008, 14, 644
14. Studt, F. and Tuczek, F. Angew. Chem., Int. Ed. 2005, 44, 5639
15. Schrock, R. R. Angew. Chem., Int. Ed. 2008, 47, 5512
16. Schenk, S., Kirchner, B., and Reiher, M. Chem.=Eur. J. 2009, 15, 5073
17. Schenk, S., Le Guennic, B., Kirchner, B., and Reiher, M. Inorg. Chem. 2008, 47, 3634
18. Hidai, M. Coord. Chem. Rev. 1999, 185-186, 99
19. Ohki, Y. and Fryzuk, M. D. Angew. Chem., Int. Ed. 2007, 46, 3180
20. Fryzuk, M. D. and Johnson, S. A. Coord. Chem. Rev. 2000, 200-202, 379
21. Hidai, M. Chem. Rev. 1995, 95, 1115
22. Allen, F. H. and Kennard, O. Chem. Des. Autom. News 1993, 8, 1-31
23. Fletcher, D. A., McMeeking, R. F., and Parkin, D. The United Kingdom Chemical Database Service. J. Chem. Inf. Comput. Sci. 1996, 36, 746; The UK Chemical Database Service: CSD version 5.31, updated May 2010.
24. Lehnert, N. and Tuczek, F. Inorg. Chem. 1999, 38, 1659
25. Mersmann, K., Horn, K. H., Bores, N., Lehnert, N., Studt, F., Paulat, F., Peters, G., Ivanovic-Burmazovic, I., van Eldik, R., and Tuczek, F. Inorg. Chem. 2005, 44, 3031
26. Lehnert, N. and Tuczek, F. Inorg. Chem. 1999, 38, 1671
27. Wiberg, N., Haring, H.-W., Huttner, G., and Friedrich, P. Chem. Ber. 1978, 111, 2708
28. Blake, A. J., McInnes, J. M., Mountford, P., Nikonov, G. I., Swallow, D., and Watkin, D. J. J. Chem. Soc., Dalton Trans. 1999, 379
29. Walsh, P. J., Carney, M. J., and Bergman, R. G. J. Am. Chem. Soc. 1991, 113, 6343
30. Li, Y., Shi, Y., and Odom, A. L. J. Am. Chem. Soc. 2004, 126, 1794
31. Parsons, T. B., Hazari, N., Cowley, A. R., Green, J. C., and Mountford, P. Inorg. Chem. 2005, 44, 8442
32. Patel, S., Li, Y., and Odom, A. L. Inorg. Chem. 2007, 46, 6373
33. Herrmann, H., Fillol, J. L., Gehrmann, T., Enders, M., Wadepohl, H., and Gade, L. H. Chem.=Eur. J. 2008, 14, 8131
34. Selby, J. D., Manley, C. D., Schwarz, A. D., Clot, E., and Mountford, P. Organometallics 2008, 27, 6479
35. Kaltsoyannis, N. and Mountford, P. J. Chem. Soc., Dalton Trans. 1999, 781
36. Cundari, T. R. Chem. Rev. 2000, 100, 807
37. Bolton, P. D., Clot, E., Cowley, A. R., and Mountford, P. J. Am. Chem. Soc. 2006, 128, 15005
38. Schrock, R. R. J. Chem. Soc., Dalton Trans. 2001, 2541
39. Thorman, J. L. and Woo, L. K. Inorg. Chem. 2000, 39, 1301
40. Banerjee, S. and Odom, A. L. Organometallics 2006, 25, 3099
41. Selby, J. D., Manley, C. D., Feliz, M., Schwarz, A. D., Clot, E., and Mountford, P. Chem. Commun. 2007, 4937
42. Herrmann, H., Fillol, J. L., Wadepohl, H., and Gade, L. H. Angew. Chem., Int. Ed. 2007, 46, 8426
43. Herrmann, H., Wadepohl, H., and Gade, L. H. Dalton Trans. 2008, 2111
44. Clulow, A. J., Selby, J. D., Cushion, M. G., Schwarz, A. D., and Mountford, P. Inorg. Chem. 2008, 47, 12049
45. Weitershaus, K., Wadepohl, H., and Gade, L. H. Organometallics 2009, 28, 3381
46. Wigley, D. E. Prog. Inorg. Chem. 1994, 42, 239
47. Mountford, P. Chem. Commun. 1997, 2127
48. Gade, L. H. and Mountford, P. Coord. Chem. Rev. 2001, 216-217, 65
49. Duncan, A. P. and Bergman, R. G. Chem. Rec. 2002, 2, 431
50. Odom, A. L. Dalton Trans. 2005, 225
51. Hazari, N. and Mountford, P. Acc. Chem. Res. 2005, 38, 839
52. Bolton, P. D. and Mountford, P. Adv. Synth. Catal. 2005, 347, 355
53. Fout, A. R., Kilgore, U. J., and Mindiola, D. J. Chem.=Eur. J. 2007, 13, 9428
54. Selby, J. D., Schulten, C., Schwarz, A. D., Stasch, A., Clot, E., Jones, C., and Mountford, P. Chem. Commun. 2008, 5101
55. Gehrmann, T., Fillol, J. L., Wadepohl, H., and Gade, L. H. Angew. Chem., Int. Ed. 2009, 48, 2152
56. Weitershaus, K., Fillol, J. L., Wadepohl, H., and Gade, L. H. Organometallics 2009, 28, 4747
57. Gehrmann, T., Fillol, J. L., Wadepohl, H., and Gade, L. H. Organometallics 2010, 29, 28
58. Tiong, P.-J., Schofield, A. D., Selby, J. D., Nova, A., Clot, E., and Mountford, P. Chem. Commun. 2010, 46, 85
59. Knobloch, D. J., Lobkovsky, E., and Chirik, P. J. Nat. Chem. 2010, 2
60. Kaplan, A. W., Polse, J. L., Ball, G. E., Andersen, R. A., and Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 11649
61. Bytschkov, I. and Doye, S. Eur. J. Org. Chem. 2003, 935
62. Doye, S. Synlett 2004, 1653
63. Hultzsch, K. C. Adv. Synth. Catal. 2005, 347, 367
64. Johnson, J. S. and Bergman, R. G. J. Am. Chem. Soc. 2001, 123, 2923
65. Cao, C., Shi, Y., and Odom, A. L. Org. Lett. 2002, 4, 2853
66. Banerjee, S., Barnea, E., and Odom, A. L. Organometallics 2008, 27, 1005
67. Ackermann, L. and Born, R. Tetrahedron Lett. 2004, 45, 9541
68. Khedkar, V., Tillack, A., Michalik, M., and Beller, M. Tetrahedron Lett. 2004, 45, 3123
69. Tillack, A., Jiao, H., Garcia Castro, I., Hartung, C. G., and Beller, M. Chem.=Eur. J. 2004, 10, 2410
70. Banerjee, S., Shi, Y., Cao, C., and Odom, A. L. J. Organomet. Chem. 2005, 690, 5066
71. Polse, J. L., Andersen, R. A., and Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 13405
72. Ward, B. D., Maisse-Francois, A., Mountford, P., and Gade, L. H. Chem. Commun. 2004, 704
73. Wang, H., Chan, H., and Xie, Z. Organometallics 2005, 24, 3772
74. Bolton, P. D., Feliz, M., Cowley, A. H., Clot, E., and Mountford, P. Organometallics 2008, 27, 6096
75. Vujkovic, N., Ward, B. D., Maisse-Francois, A., Wadepohl, H., Mountford, P., and Gade, L. H. Organometallics 2007, 26, 5522
76. Walsh, P. J., Baranger, A. M., and Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708
77. Basuli, F., Aneetha, H., Huffman, J. C., and Mindiola, D. J. J. Am. Chem. Soc. 2005, 127, 17992
78. Pugh, S. M., Clark, H. S. C., Love, J. B., Blake, A. J., Cloke, F. G. N., and Mountford, P. Inorg. Chem. 2000, 39, 2001
79. Blake, A. J., Collier, P. E., Gade, L. H., Mountford, P., Lloyd, J., Pugh, S. M., Schubart, M., Skinner, M. E. G., and Trösch, J. M. Inorg. Chem. 2001, 40, 870
80. Doxsee, K. M., Farahi, J. B., and Hope, H. J. Am. Chem. Soc. 1991, 113, 8889
81. Bailey, B. C., Fout, A. R., Fan, H., Tomaszewski, J., Huffman, J. C., Gary, J. B., Johnson, M. J. A., and Mindiola, D. J. J. Am. Chem. Soc. 2007, 129, 2234
82. Lee, S. Y. and Bergman, R. G. Tetrahedron 1995, 51, 4255
83. Jordan, R. B. Reaction Mechanisms of Inorganic and Organometallic Systems; Oxford University Press: Oxford, 1998.
84. Hansch, C., Leo, A., and Taft, R. W. Chem. Rev. 1991, 91, 165
85. Stewart, P. J., Blake, A. J., and Mountford, P. Inorg. Chem. 1997, 36, 3616
86. Hartwig, J. F., Cook, K. S., Hapke, M., Incarvito, C. D., Fan, Y., Webster, C. E., and Hall, M. B. J. Am. Chem. Soc. 2005, 127, 2538
87. Nguyen, T. A. Frontier Orbitals: A Practical Manual; John Wiley & Sons: Chichester, 2007.
88. Polse, J. L., Kaplan, A. W., Andersen, R. A., and Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 6316
89. Hanna, T. E., Keresztes, I., Lobkovsky, E., Bernskoetter, W. H., and Chirik, P. J. Organometallics 2004, 23, 3448
90. Frisch, M. J.; et al. Gaussian 03, Revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
91. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
92. Perdew, J. P. and Wang, Y. Phys. Rev. B 1992, 45, 13244
93. Andrae, D., Haussermann, U., Dolg, M., Stoll, H., and Preuss, H. Theor. Chim. Acta 1990, 77, 123
94. Hariharan, P. C. and Pople, J. A. Theor. Chim. Acta 1973, 28, 213
95. Bergner, A., Dolg, M., Kuchle, W., Stoll, H., and Preuss, H. Mol. Phys. 1993, 30, 1431
96. Hollwarth, A., Bohme, H., Dapprich, S., Ehlers, A. W., Gobbi, A., Jonas, V., Kohler, K. F., Stagmann, R., Veldkamp, A., and Frenking, G. Chem. Phys. Lett. 1993, 203, 237