Iridium- and rhodium-catalyzed dehydrogenative silylations of C(sp 3) - H bonds adjacent to a nitrogen atom using hydrosilanes

Chemistry - An Asian Journal

Volumn 8, Issue 12, 2013, Pages 2970-2973

  Mita, Tsuyoshi ^a   Michigami, Kenichi ^a   Sato, Yoshihiro ^a,b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

C H activation; carbon dioxide; iridium; pyridine; rhodium

Indexed keywords

1 ,5-CYCLOOCTADIENE; C-H ACTIVATION; DEHYDROGENATIVE COUPLING; IRIDIUM CATALYSIS; NITROGEN ATOM; RHODIUM CATALYSIS; RHODIUM CATALYSTS; RHODIUM-CATALYZED;

ACTIVATION ANALYSIS; CARBON DIOXIDE; CATALYSIS; NITROGEN; PYRIDINE; RHODIUM;

IRIDIUM;

CARBON DIOXIDE; IRIDIUM; NITROGEN; ORGANOMETALLIC COMPOUND; PYRIDINE; RHODIUM; SILANE DERIVATIVE;

ARTICLE; C H ACTIVATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; SYNTHESIS;

C H ACTIVATION; CARBON DIOXIDE; IRIDIUM; PYRIDINE; RHODIUM;

CATALYSIS; HYDROGENATION; IRIDIUM; MOLECULAR STRUCTURE; NITROGEN; ORGANOMETALLIC COMPOUNDS; RHODIUM; SILANES;

EID: 84888369128     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201300930     Document Type: Article

References (74)

1. For selected reviews on C - H activation, see R. Jazzar, J. Hitce, A. Renaudat, J. Sofack-Kreutzer, O. Baudoin, Chem. Eur. J. 2010, 16, 2654
2. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
3. J. J. Mousseau, A. B. Charette, Acc. Chem. Res. 2013, 46, 412.
4. For Ir-catalyzed C - H silylations, see W. A. Gustavson, P. S. Epstein, M. D. Curtis, Organometallics 1982, 1, 884
5. T. Ishiyama, K. Sato, Y. Nishio, N. Miyaura, Angew. Chem. 2003, 115, 5504
6. Angew. Chem. Int. Ed. 2003, 42, 5346
7. T. Ishiyama, K. Sato, Y. Nishio, T. Saiki, N. Miyaura, Chem. Commun. 2005, 5065
8. T. Saiki, Y. Nishio, T. Ishiyama, N. Miyaura, Organometallics 2006, 25, 6068
9. B. Lu, J. R. Falck, Angew. Chem. 2008, 120, 7618
10. Angew. Chem. Int. Ed. 2008, 47, 7508
11. E. M. Simmons, J. F. Hartwig, J. Am. Chem. Soc. 2010, 132, 17092
12. E. M. Simmons, J. F. Hartwig, Nature 2012, 483, 70.
13. For Rh-catalyzed C - H silylations, see T. Sakakura, Y. Tokunaga, T. Sodeyama, M. Tanaka, Chem. Lett. 1987, 16, 2375
14. P. I. Djurovich, A. R. Dolich, D. H. Berry, J. Chem. Soc. Chem. Commun. 1994, 1897
15. K. Ezbiansky, P. I. Djurovich, M. LaForest, D. J. Sinning, R. Zayes, D. H. Berry, Organometallics 1998, 17, 1455
16. M. Tobisu, Y. Ano, N. Chatani, Chem. Asian J. 2008, 3, 1585
17. T. Ureshino, T. Yoshida, Y. Kuninobu, K. Takai, J. Am. Chem. Soc. 2010, 132, 14324
18. Y. Kuninobu, K. Yamauchi, N. Tamura, T. Seiki, K. Takai, Angew. Chem. 2013, 125, 1560
19. Angew. Chem. Int. Ed. 2013, 52, 1520
20. Y. Kuninobu, T. Nakahara, H. Takeshima, K. Takai, Org. Lett. 2013, 15, 426.
21. For other transition-metal-catalyzed C - H silylations, see M. Ishikawa, S. Okazaki, A. Naka, H. Sakamoto, Organometallics 1992, 11, 4135
22. Y. Uchimaru, A. M. M. E. Sayed, M. Tanaka, Organometallics 1993, 12, 2065
23. M. Ishikawa, A. Naka, J. Ohshita, Organometallics 1993, 12, 4987
24. N. A. Williams, Y. Uchimaru, M. Tanaka, J. Chem. Soc. Chem. Commun. 1995, 1129
25. A. Naka, K. K. Lee, K. Yoshizawa, T. Yamabe, M. Ishikawa, Organometallics 1999, 18, 4524
26. F. Kakiuchi, M. Matsumoto, M. Sonoda, T. Fukuyama, N. Chatani, S. Murai, N. Furukawa, Y. Seki, Chem. Lett. 2000, 29, 750
27. F. Kakiuchi, K. Igi, M. Matsumoto, N. Chatani, S. Murai, Chem. Lett. 2001, 30, 422
28. F. Kakiuchi, K. Igi, M. Matsumoto, T. Hayamizu, N. Chatani, S. Murai, Chem. Lett. 2002, 31, 396
29. N. A. Williams, Y. Uchimaru, M. Tanaka, Dalton Trans. 2003, 236
30. F. Kakiuchi, M. Matsumoto, K. Tsuchiya, K. Igi, T. Hayamizu, N. Chatani, S. Murai, J. Organomet. Chem. 2003, 686, 134
31. N. Tsukada, J. F. Hartwig, J. Am. Chem. Soc. 2005, 127, 5022
32. M. Murata, N. Fukuyama, J. Wada, S. Watanabe, Y. Masuda, Chem. Lett. 2007, 36, 910
33. H. Ihara, M. Suginome, J. Am. Chem. Soc. 2009, 131, 7502.
34. 3)-H silylations, see A. D. Sadow, T. D. Tilley, Angew. Chem. 2003, 115, 827
35. Angew. Chem. Int. Ed. 2003, 42, 803
36. F. Kakiuchi, K. Tsuchiya, M. Matsumoto, E. Mizushima, N. Chatani, J. Am. Chem. Soc. 2004, 126, 12792
37. A. D. Sadow, T. D. Tilley, J. Am. Chem. Soc. 2005, 127, 643
38. J. M. Larsson, T. S. N. Zhao, K. J. Szabó, Org. Lett. 2011, 13, 1888
39. H. Ihara, A. Ueda, M. Suginome, Chem. Lett. 2011, 40, 916.
40. G. R. Jones, Y. Landais, Tetrahedron 1996, 52, 7599.
41. T. Hiyama, E. Shirakawa, Top. Curr. Chem. 2002, 219, 61
42. Y. Nakao, T. Hiyama, Chem. Soc. Rev. 2011, 40, 4893.
43. 2, see F. Effenberger, W. Spiegler, Chem. Ber. 1985, 118, 3900
44. M. Ohno, H. Tanaka, M. Komatsu, Y. Ohshiro, Synlett 1991, 919
45. R. P. Singh, J. M. Shreeve, Chem. Commun. 2002, 1818
46. L. A. Babadzhanova, N. V. Kirij, Y. L. Yagupolskii, J. Fluorine Chem. 2004, 125, 1095
47. K. I. Petko, S. Y. Kot, L. M. Yagupolskii, J. Fluorine Chem. 2008, 129, 301
48. T. Mita, J. Chen, M. Sugawara, Y. Sato, Org. Lett. 2012, 14, 6202
49. M. Yonemoto-Kobayashi, K. Inamoto, Y. Tanaka, Y. Kondo, Org. Biomol. Chem. 2013, 11, 3773.
50. T. Mita, K. Michigami, Y. Sato, Org. Lett. 2012, 14, 3462.
51. 3) - H bonds adjacent to a nitrogen atom, see:, S. Kawamorita, T. Miyazaki, T. Iwai, H. Ohmiya, M. Sawamura, J. Am. Chem. Soc. 2012, 134, 12924.
52. For electronic effects of the pyridine ring on C-H triborylation, see T. Mita, Y. Ikeda, K. Michigami, Y. Sato, Chem. Commun. 2013, 49, 5601; For a related work, see
53. S. Kawamorita, R. Murakami, T. Iwai, M. Sawamura, J. Am. Chem. Soc. 2013, 135, 2947.
54. N. Dastbaravardeh, M. Schnürch, M. D. Mihovilovic, Org. Lett. 2012, 14, 1930.
55. The reaction seemed to proceed via a σ-CAM (σ-complex- assisted metathesis) process. See:, J. F. Hartwig, K. S. Cook, M. Hapke, C. D. Incarvito, Y. Fan, C. E. Webster, M. B. Hall, J. Am. Chem. Soc. 2005, 127, 2538. For a review on a σ-CAM, see
56. R. N. Perutz, S. Sabo-Etienne, Angew. Chem. 2007, 119, 2630
57. Angew. Chem. Int. Ed. 2007, 46, 2578.
58. 2 incorporation reactions, see T. Sakakura, J.-C. Choi, H. Yasuda, Chem. Rev. 2007, 107, 2365
59. M. Mori, Eur. J. Org. Chem. 2007, 4981
60. A. Correa, R. Martín, Angew. Chem. 2009, 121, 6317
61. Angew. Chem. Int. Ed. 2009, 48, 6201
62. S. N. Riduan, Y. Zhang, Dalton Trans. 2010, 39, 3347
63. I. I. F. Boogaerts, S. P. Nolan, Chem. Commun. 2011, 47, 3021
64. L. Ackermann, Angew. Chem. 2011, 123, 3926
65. Angew. Chem. Int. Ed. 2011, 50, 3842
66. Y. Zhang, S. N. Riduan, Angew. Chem. 2011, 123, 6334
67. Angew. Chem. Int. Ed. 2011, 50, 6210
68. M. Cokoja, C. Bruckmeier, B. Rieger, W. A. Herrmann, F. E. Kühn, Angew. Chem. 2011, 123, 8662
69. Angew. Chem. Int. Ed. 2011, 50, 8510
70. Y. Tsuji, T. Fujihara, Chem. Commun. 2012, 48, 9956.
71. T. Mita, J. Chen, M. Sugawara, Y. Sato, Angew. Chem. 2011, 123, 1429
72. Angew. Chem. Int. Ed. 2011, 50, 1393
73. T. Mita, M. Sugawara, H. Hasegawa, Y. Sato, J. Org. Chem. 2012, 77, 2159
74. T. Mita, Y. Higuchi, Y. Sato, Chem. Eur. J. 2013, 19, 1123.