Competitive ArC-H and ArC-X (X = Cl, Br) activation in halobenzenes at cationic titanium centers

Journal of the American Chemical Society

Volumn 128, Issue 10, 2006, Pages 3303-3312

  Ma, Kuangbiao ^a   Piers, Warren E ^a   Parvez, Masood ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CHEMICAL BONDS; HALOGEN COMPOUNDS; HEATING; POSITIVE IONS;

BOND ACTIVATION PROCESSES; BROMOBENZENE; CATIONIC TITANIUM CENTERS; HALOBENZENES;

TITANIUM;

BENZENE DERIVATIVE; BROMOBENZENE; CARBON; CATION; CHLOROBENZENE; HALIDE; HALOBENZENE; HALOGEN; HYDROGEN; METAL COMPLEX; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTAL STRUCTURE; GAS CHROMATOGRAPHY; HALOGENATION; HEATING; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THERMOSTABILITY; X RAY CRYSTALLOGRAPHY;

EID: 33644957984     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0583618     Document Type: Article

References (70)

1. (a) Metal Catalyzed Cross-Coupling Reactions, 2nd ed.; de Miejere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany. 2004.
2. (b) Negishi, E. I., Ed. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: New York, 2002.
3. Recent mechanistic studies on Ar-X activation: (a) Barrios-Landeros, F.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 6944.
4. (b) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
5. (c) Lewis, A. K. de K.; Caddick, S.; Cloke, F. G. N.; Billingham, N. C.; Hitchcock, P. B.; Leonard, J. J. Am. Chem. Soc. 2003, 125, 10066.
6. (d) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
7. (e) Galardon, E.; Ramdeehul, S.; Brown, J. M.; Cowley, A.; Hii, K. K.; Jutand, A. Angew. Chem., Int. Ed. 2002, 41, 1760.
8. Recent examples employing late metals: (a) Fan, L.; Parkin, S.; Ozerov, O. V. J. Am. Chem. Soc. 2005, 127, 16772.
9. (b) Ben-Ari, E.; Gandelman, M.; Rozenberg, H.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2003, 125, 4714.
10. (c) Zhang, X.; Kanzelberger, M.; Emge, T. J.; Goldman, A. S. J. Am. Chem. Soc. 2004, 126, 13192.
11. (a) Jones, W. D. Dalton Trans. 2003, 3991 and references therein,
12. (b) Turculet, L.; Tilley, T. D. Organometallics 2002, 21, 3961.
13. (c) Kraft, B. M.; Jones, W. D. J. Am. Chem. Soc. 2002, 124, 8681.
14. (d) Clot, E.; Megret, C.; Kraft, B. M.; Eisenstein, O.; Jones, W. D. J. Am. Chem. Soc. 2004, 126, 5647.
15. Wu, F.; Dash, A.; Jordan, R. F. J. Am. Chem. Soc. 2004, 126, 15360.
16. Booij, M.; Deelman, B.-J.; Duchateau, R.; Postma, D. S.; Meetsma, A.; Teuben, J. H. Organometallics 1993, 12, 3531.
17. Maron, L.; Werkema, E. L.; Perrin, L.; Eisenstein, O.; Andersen, R. A. J. Am. Chem. Soc. 2005, 127, 279.
18. 0 metal hydrides: (a) Gavenonis, J.; Tilley, T. D. Organometallics 2004, 23, 31.
19. (b) Deutsch, P. P.; Maguire, J. A.; Jones, W. D.; Eisenberg, R. Inorg. Chem. 1990, 29, 686.
20. (a) Ephritikhine, M. Chem. Rev. 1997, 97, 2193.
21. (b) Emslie, D. J.; Piers, W. E. Coord. Chem. Rev. 2002, 233-34, 129.
22. Ma, K.; Piers, W. E.; Gao, Y.; Parvez, M. J. Am. Chem. Soc. 2004, 126, 5668.
23. Stephan, D. W. Organometallics 2005, 24, 2548 and references therein.
24. Chien, J. C. W.; Tsai, W.-M.; Rausch, M. D. J. Am. Chem. Soc. 1991, 113, 8570.
25. 13b unless this is the thermodynamic isomer in this system,
26. (b) 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.
27. 5X that six hydrogen or deuterium atoms are incorporated. Cationic hydride 1 has also been observed to rapidly hydrogenate anthracene to tetrahydroanthracene (Ma, K.; Piers, W. E. Unpublished results).
28. (a) Cabrera, L.; Hollink, E.; Stewart, J. C.; Wei, P.; Stephan, D. W. Organometallics 2005, 24, 1091.
29. (b) Yue, N. L. S.; Stephan, D. W. Organometallics 2001, 20, 2303.
30. See for example: Zhang, S.; Piers, W. E. Organometallics 2001, 20, 2088.
31. Full details on this particular structure can be found in the Supporting Information of ref 10.
32. Klouras, N.; Nastopoulos, V.; Demekopoulos, I.; Leban, I. Z. Anorg. Allg. Chem. 1993, 619, 1927.
33. Bochmann, M.; Jaggar, A. J.; Wilson, L. M.; Hursthouse, M. B.; Motevalli, M. Polyhedron 1989, 8, 1838.
34. 2, which contains both phosphinimido (Ti-N = 1.777(4) Å) and phosphinimine (Ti-N = 2.134(4) Å) ligands, was observed: Grun, M.; Harms, K.; zu Kocker, R. M.; Dehnicke, K.; Goesmann, H. Z. Anorg. Allg. Chem. 1996, 622, 1091.
35. Kraft, B. M.; Jones, W. D. J. Organomet. Chem. 2002, 658, 132.
36. Halogen carbon bond cleavage in aliphatic RX substrates by Ti(III): (a) Yanlong, Q.; Guisheng, L.; Huang, Y. Z. J. Organomet. Chem. 1990, 381, 29.
37. (b) Qian, Y.; Guisheng, Z.; Xiaofan, H.; Huang, Y. Z. Synlett 1991, 489.
38. (c) Covert, K. J.; Mayol, A.-R.; Wolczanski, P. T. Inorg. Chim. Acta 1997, 263, 263.
39. (d) Agapie, T.; Dianescu, P. L.; Mindiola, D. J.; Cummins, C. C. Organometallics 2002, 21, 1329.
40. (e) C-O bond cleavage: Rajanbabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986.
41. Lagoa, A. L. C.; Diogo, H. P.; Dias, M. P.; Minas da Piedade, M. E.; Amaral, L. M. P. F.; Ribeiro da Silva, M. A. V.; Martinho Simoes, J. A.; Guedes, R. C.; Costa Cabral, B. J.; Schwarz, K.; Epple, M. Chem.-Eur. J. 2001, 7, 483 and references therein.
42. 24b
43. (b) Andrieux, C. P.; Blocman, C.; Dumas-Bouchiat, J.-M.; Saveant, J.-M. J. Am. Chem. Soc. 1979, 101, 3432.
44. 25b.c but it is not clear that it would be kinetically significant under our conditions, especially in light of the significant quantities of biphenyl produced,
45. (b) Mebel, A. M.; Lin, M. C.; Yu, T.; Morokuma, K. J. Phys. Chem. A 1997, 101, 3189.
46. (c) Park, J.; Dyakov, I. V.; Lin, M. C. J. Phys. Chem. A 1997, 101, 8839.
47. - generated as described,
48. (b) Chesnut, D. B.; Sloan, G. J. J. Chem. Phys. 1960, 33, 637.
49. (c) Volz, H.; Lotsch, W.; Schnell, H.-W. Tetrahedron 1970, 26, 5343.
50. Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391.
51. (a) Jordan, R. F.; Dasher, W. E.; Echols, S. F. J. Am. Chem. Soc. 1986, 108, 1718.
52. (b) Jordan, R. F.; Bajgur, C. S.; Willett, R.; Scott, B. J. Am. Chem. Soc. 1986, 108, 7410.
53. (c) Jordan, R. F.; Lapointe, R. E.; Bajgur, C. S.; Willett, R. J. Am. Chem. Soc. 1987, 109, 4111.
54. (a) Chase, P. A.; Piers, W. E.; Parvez, M. Organometallics 2000, 19, 2040.
55. (b) Luinstra, G. A.; ten Cate, L. C.; Heeres, H. J.; Pattiasina, J. W.; Meetsma, A.; Teuben, J. H. Organometallics 1991, 10, 3227.
56. (c) Pattiasina, J.; Heeres, H. J.; van Bolhuis, F.; Meetsma, A.; Teuben, J. H.; Spek, A. L. Organometallics 1987, 6, 1004.
57. The intensity of the ESR signal for the trityl radical, in equilibrium with its dimer, is ∼30 times lower than the signal observed for the Ti(III) species present during the reaction.
58. 1 to a thermodynamic mixture governed by an equilibrium isotope effect is slow under these conditions.
59. Bouwkamp, M. W.; Budzelaar, P. H. M.; Gercama, J.; Del Hierro Morales, I.; de Wolf, J.; Meetsma, A.; Troyanov, S. I.; Teuben, J. H.; Hessen, B. J. Am. Chem. Soc. 2005, 127, 14310.
60. 33b
61. (b) Kulawiec, R. J.; Crabtree, R. H. Coord. Chem. Rev. 1990, 99, 89.
62. (a) Stoekland, R. A., Jr.; Jordan, R. F. J. Am. Chem. Soc. 2000, 122, 6315.
63. (b) Shen, H.; Jordan, R. F. Organometallics 2003, 22, 2080.
64. (c) Stockland, R. A., Jr.; Foley, S. R.; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 796.
65. (d) Strazisar, S. A.; Wolezanski, P. T. J. Am. Chem. Soc. 2001, 123, 4728.
66. (a) Kraft, B. M.; Lachicotte, R. J.; Jones, W. D. J. Am. Chem. Soc. 2001, 123, 10973.
67. (b) van Rooyen, P. H.; Schindehutte, M.; Lotz, S. Organometallics 1992, 11, 1104.
68. This reaction was followed only to 65% completion.
69. Stephan, D. W.; Stewart, J. C.; Guérin, F.; Courtney, S.; Kickam, J.; Hollink, E.; Beddie, C.; Graham, T.; Wei, P.; Spence, R. E. v. H.; Xu, W.; Koch, L.; Gao, X.; Harrison, D. G. Organometallics 2003, 22, 1937.
70. Roberts, J. D.; Semenow, D. A.; Simmons, H. E.; Carlsmith, L. A. J. Am. Chem. Soc. 1956, 78, 601.