Regioselective aromatic C-H silylation of five-membered heteroarenes with fluorodisilanes catalyzed by iridium(I) complexes

Chemical Communications

Volumn , Issue 40, 2005, Pages 5065-5067

  Ishiyama, Tatsuo ^a   Sato, Kazuaki ^a   Nishio, Yukihiro ^a   Saiki, Takeaki ^a   Miyaura, Norio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,10 PHENANTHROLINE; 1,2 DI TERT BUTYL 1,1,2,2 TETRAFLUORODISILANE; 2 TERT BUTYL 1,10 PHENANTHROLINE; CARBON; HYDROGEN; IRIDIUM COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYSIS; COMPLEX FORMATION; HIGH TEMPERATURE; QUANTUM YIELD; REACTION ANALYSIS; SILYLATION; STEREOCHEMISTRY; STEREOSPECIFICITY; TEMPERATURE DEPENDENCE;

EID: 27644566181     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b511171d     Document Type: Article

References (37)

1. For a review, see: F. Kakiuchi and N. Chatani, Adv. Synth. Catal., 2003, 345, 1077.
2. (a) T. Sakakura, Y. Tokunaga, T. Sodeyama and M. Tanaka, Chem. Lett., 1987, 2375;
3. (b) M. Ishikawa, S. Okazaki, A. Naka and H. Sakamoto, Organometallics, 1992, 11, 4135;
4. (c) M. Ishikawa, A. Naka and J. Ohshita, Organometallics, 1993, 12, 4987;
5. (d) N. A. Williams, Y. Uchimaru and M. Tanaka, J. Chem. Soc., Chem. Commun., 1995, 1129;
6. (e) A. Naka, K. K. Lee, K. Yoshizawa, T. Yamabe and M. Ishikawa, Organometallics, 1999, 18, 4524;
7. (f) N. A. Williams, Y. Uchimaru and M. Tanaka, Dalton Trans., 2003, 236.
8. (a) W. A. Gustavson, P. S. Epstein and M. D. Curtis, Organometallics, 1982, 1, 884;
9. (b) Y. Uchimaru, A. M. M. El Sayed and M. Tanaka, Organometallics, 1993, 12, 2065;
10. (c) K. Ezbiansky, P. I. Djurovich, M. LaForest, D. J. Sinning, R. Zayes and D. H. Berry, Organometallics, 1998, 17, 1455;
11. (d) F. Kakiuchi, K. Igi, M. Matsumoto, N. Chatani and S. Murai, Chem. Lett., 2001, 422;
12. (e) F. Kakiuchi, K. Igi, M. Matsumoto, T. Hayamizu, N. Chatani and S. Murai, Chem. Lett., 2002, 396;
13. (f) F. Kakiuchi, M. Matsumoto, K. Tsuchiya, K. Igi, T. Hayamizu, N. Chatani and S. Murai, J. Organomet. Chem., 2003, 686, 134.
14. T. Ishiyama, K. Sato, Y. Nishio and N. Miyaura, Angew. Chem., Int. Ed., 2003, 42, 5346.
15. The catalysts were also effective for aromatic C-H borylation, see: (a) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 390;
16. (b) J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama and N. Miyaura, Tetrahedron Lett., 2002, 43, 5649;
17. (c) T. Ishiyama, J. Takagi, J. F. Hartwig and N. Miyaura, Angew. Chem., Int. Ed., 2002, 41, 3056;
18. (d) T. Ishiyama, J. Takagi, Y. Yonekawa, J. F. Hartwig and N. Miyaura, Adv. Synth. Catal., 2003, 345, 1103;
19. (e) T. Ishiyama, Y. Nobuta, J. F. Hartwig and N. Miyaura, Chem. Commun., 2003, 2924;
20. (f) T. Ishiyama and N. Miyaura, J. Organomet. Chem., 2003, 680, 3;
21. (g) T. Ishiyama and N. Miyaura, Chem. Rec., 2004, 3, 271;
22. (h) K. Kurotobi, M. Miyauchi, K. Takakura, T. Marufuji and Y. Sugihara, Eur. J. Org. Chem., 2003, 3663;
23. (i) A. Datta, A. Köllhofer and H. Plenio, Chem. Commun., 2004, 1508;
24. (j) D. N. Coventry, A. S. Batsanov, A. E. Goeta, J. A. K. Howard, T. B. Marder and R. N. Perutz, Chem. Commun., 2005, 2172;
25. (k) G. A. Chotana, M. A. Rak and M. R. Smith, III, J. Am. Chem. Soc., 2005, 127, 10539.
26. For a theoretical study, see: (l) H. Tamura, H. Yamazaki, H. Sato and S. Sakaki, J. Am. Chem. Soc., 2003, 125, 16114.
27. (a) T. Hiyama and E. Shirakawa, Top. Curr. Chem., 2002, 219, 61;
28. (b) S. E. Denmark and R. F. Sweis, Acc. Chem. Res., 2002, 35, 835.
29. (a) S. Oi, M. Moro and Y. Inoue, Organometallics, 2001, 20, 1036;
30. (b) T.-S. Huang and C.-J. Li, Chem. Commun., 2001, 2348;
31. (c) K. Fagnou and M. Lautens, Chem. Rev., 2003, 103, 169.
32. M. P. T. Sjögren, S. Hansson, B. Åkermark and A. Vitagliano, Organometallics, 1994, 13, 1963.
33. J. J. Li and G. W. Gribble, in Tetrahedron Organic Chemistry Series, ed. J. E. Baldwin and R. M. Williams, Pergamon, Amsterdam, 2000, vol. 20, pp. 233.
34. D. P. Curran, in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon, Oxford, 1991, vol. 4, pp. 715.
35. (a) L. Dong, S. B. Duckett, K. F. Ohman and W. D. Jones, J. Am. Chem. Soc., 1992, 114, 151;
36. (b) T. Morikita, M. Hirano, A. Sasaki and S. Komiya, Inorg. Chim. Acta, 1999, 291, 341;
37. (c) S. N. Ringelberg, A. Meetsma, B. Hessen and J. H. Teuben, J. Am. Chem. Soc., 1999, 121, 6082.