Iridium-Catalyzed Borylation of Benzene with Diboron. Theoretical Elucidation of Catalytic Cycle Including Unusual Iridium(V) Intermediate

Journal of the American Chemical Society

Volumn 125, Issue 51, 2003, Pages 16114-16126

  Tamura, Hitoshi ^a   Yamazaki, Hideki ^b,c   Sato, Hirofumi ^a   Sakaki, Shigeyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

^b KUMAMOTO UNIVERSITY   (Japan)

^c OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; BORON; CATALYSTS; CHEMICAL ACTIVATION; CHEMICAL BONDS; DISCRETE FOURIER TRANSFORMS; IRIDIUM; ORGANOMETALLICS; OXIDATION;

ACTIVATION BARRIERS; REDUCTIVE ELIMINATION;

BENZENE;

BENZENE; BORON DERIVATIVE; IRIDIUM;

ARTICLE; BORYLATION; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; COMPLEX FORMATION; OXIDATION; REDUCTION;

EID: 0345733884     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0302937     Document Type: Article

References (59)

1. Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995.
2. Iverson, C. N.; Smith, M. R., III. J. Am. Chem. Soc. 1999, 121, 7696. This work first reported the transition-metal-catalyzed borylation of aromatic compounds.
3. (a) Cho, J. Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E.; Smith, M. R., III. Science 2002, 295, 305.
4. (b) Cho, J. Y.; Iverson, C. N.; Smith, M. R., III. J. Am. Chem. Soc. 2000, 122, 12868.
5. (a) Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390.
6. (b) Ishiyama, T.; Takagi, J.; Hartwig, J.; Miyaura, N. Angew. Chem., Int. Ed. 2002, 114, 3182.
7. Shimada, S.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B. Angew. Chem., Int. Ed. 2001, 40, 2168.
8. Takagi, J.; Sato, K.; Hartwig, J. F.; Ishiyama, T.; Miyaura, N. Tetrahedoron Lett. 2002, 43, 5649.
9. (a) Waltz, K. M.; He, X.; Muhoro, C.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11357.
10. (b) Waltz, K. M.; Hartwig, J. F. Science 1997, 277, 211.
11. (c) Waltz, K. M.; Muhoro, C. N.; Hartwig, J. F. Organometallics 1999, 18, 3383.
12. (d) Waltz, K. M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 11358.
13. Nguyen, P.; Blom, H. P.; Westcott, S. A.; Taylor, N. J.; Marder, T. B. J. Am. Chem. Soc. 1993, 115, 9329.
14. Gilbert, T. M.; Hollander, F. J.; Bergman, R. G. J. Am. Chem. Soc. 1985, 107, 3508.
15. Kawamura, K.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 8422.
16. (a) Fernandez, M.-J.; Bailey, P. M.; Bentz, P. O.; Ricci, J. S.; Koetzle, T. F.; Maitlis, P. M. J. Am. Chem. Soc. 1984, 106, 5458.
17. (b) Ricci, J. S., Jr.; Koetzle, T. F.; Fernandez, M. J.; Maitlis, P. M.; Green, J. C. J. Organomet. Chem. 1986, 299, 383.
18. Gilbert, T. M.; Hollander, F. J.; Bergman, R. G. J. Am. Chem. Soc. 1984, 106, 5458.
19. Loza, M.; Faller, J. W.; Crabtree, R. H. Inorg. Chem. 1995, 32, 383.
20. Cotton, F. A.; Wilkinson, G.; Murillo, C. A.; Bochmann, M. Advanced Inorganic Chemistry, 6th ed.; John Wiley & Sons: New York, 1999; p 1059.
21. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1985; pp 312 and 328.
22. Wink, P. A.; Ford, P. C. J. Am. Chem. Soc. 1986, 108, 4838.
23. Buchanan, J. M.; Stryker, J. M.; Bergman, R. G., J. Am. Chem. Soc. 1986, 108, 1537.
24. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
25. (b) Becke, A. D. J. Chem. Phys. 1983, 98, 5648.
26. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
27. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
28. Ditchfiled, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724.
29. Hariharan, P. C.; Pople, J. A. Mol. Phys. 1974, 27, 209.
30. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
31. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
32. Couty, M.; Hall, M. B. J. Comput. Chem. 1996, 17, 1359
33. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb. M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Cliford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian Inc.: Pittsburgh, PA, 1998.
34. Reed, A. E.; Curtis, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 849 and references therein.
35. Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 2000, 19, 3895.
36. (a) Sakaki, S.; Ieki, M. J. Am. Chem. Soc., 1991, 113, 5063.
37. (b) Sakaki, S.; Ieki, M. J. Am. Chem. Soc., 1993, 115, 2373.
38. (c) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. Inorg. Chem. 1994, 33, 1660.
39. (d) Sakaki, S.; Biswas, B.; Sugimoto, M. J. Chem. Soc., Dalton Trans. 1997, 803.
40. (e) Sakaki, S.; Biswas, B.; Sugimoto, M. Organometallics, 1998, 17, 1278.
41. (f) Sakaki, S.; Mizoe, N.; Musashi, Y.; Biswas, B.; Sugimoto, M. J. Phys. Chem. 1998, 102, 8027.
42. Obara, S.; Kitaura, K.; Morokuma, K. J. Am. Chem. Soc. 1984, 106, 7472.
43. Low, J. J.; Goddard, W. A. Organometallics 1986, 5, 609.
44. (a) Blomherg, M. R. A.; Siegbahn, P. E. M.; Nagashima, U.; Wennerberg, J. J. Am. Chem. Soc. 1991, 113, 424.
45. (b) Sieghahn, P. E. M.; Blomberg, M. R. A.; Svensson, M. J. Am. Chem. Soc. 1993, 115, 4191.
46. (c) Siegbahn, P. E. M. Organometallics 1994, 13, 2833.
47. (d) Siegbahn, P. E. M. J. Am. Chem. Soc. 1996, 118, 1487.
48. Baker, R. T.; Calabrese, J. C.; Westcott, S. A.; Nguyen, P.; Marder, T. B. J. Am. Chem. Soc. 1993, 115, 4367.
49. Lesley, G.; Nguyen, P.; Taylor, N. J.; Marder, T. B.; Scott, A. J.; Clegg, W.; Norman, N. C. Organometallics 1996, 15, 5137.
50. Sakaki, S.; Kikuno, T. Inorg. Chem. 1997, 36, 226.
51. Cui, Q.; Musaev, D. G.; Morokuma, K. Organometallics, 1997, 16, 1355.
52. Tamura, H.; Yamazaki, H.; Sato, H.; Sakaki, S. To be published.
53. Hartwig, J. F.; Muhoro, C. N.; He, X.; Eisenstein, O.; Bosque, R.; Maseras, F. J. Am. Chem. Soc., 1996, 118, 10936.
54. The charge-transfer from benzene to Beg1 is considered not to participate in this population change, because the Beg1 plane is almost perpendicular to the benzene plane and the empty p orbital of Beg1 cannot interact with the π orbital of benzene. One plausible reason of this population increase of Beg1 is that Beg1 slightly shifts from a position trans to the N atom of bpy in 14 but it is at a position just trans to the N atom in 15. As a result, the electron donation of Beg1 to the Ir center is suppressed by the trans-influence of bpy in 15, which leads to the increase in the electron population of Beg1 in 15.
55. For instance, (a) Dedieu, A. Chem. Rev. 2000, 100, 543, and references therein.
56. (b) Sakaki, S. Bull. Korean Chem. Soc. 2003, 24, 829, and references there.
57. For instance, (a) Sargent, A. L.; Hall, M. B. Inorg. Chem. 1992, 31, 317.
58. (b) Sargent, A. L.; Hall, M. B.; Guest, M. F. J. Am. Chem. Soc. 1992, 114, 517.
59. (c) Sakaki, S.; Ujino, Y.; Sugimoto, M. Bull. Chem. Soc. Jpn. 1996, 69, 3047.