Rhodium acetate/base-catalyzed N-silylation of indole derivatives with hydrosilanes

Chemical Communications

Volumn 48, Issue 74, 2012, Pages 9269-9271

  Itagaki, Shintaro ^a   Kamata, Keigo ^a   Yamaguchi, Kazuya ^a   Mizuno, Noritaka ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETATE RHODIUM; ACETIC ACID DERIVATIVE; ACETONITRILE; BASE; CARBAZOLE DERIVATIVE; INDOLE DERIVATIVE; PYRROLE; RHODIUM DERIVATIVE; SILANE DERIVATIVE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL INTERACTION; HYDROGEN BOND; HYDROGENATION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SILYLATION; SOLVENT EFFECT;

EID: 84865206862     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc34381a     Document Type: Article

References (51)

1. S. E. Denmark and R. F. Sweis, in Metal-Catalyzed Cross-Coupling Reactions, ed. A. D. Meijere and F. Diederich, Wiley, Weinheim, 2004, vol. 1, pp. 163-216
2. N. Miyaura, A. Suzuki, Chem. Rev., 1995, 95, 7
3. K. Hirabayashi, J. Kawashima, Y. Nishihara, A. Mori, T. Hiyama, Org. Lett., 1999, 1, 299
4. M. Negwer, Organic-Chemical Drugs and Their Synonyms: An International Survey, Akademic Verlag, Berlin, 1994
5. P. N. Craig, in Comprehensive Medicinal Chemistry, ed. C. J. Drayton, Pergamon, New York, 1991, vol. 8
6. A. K. Franz, Curr. Opin. Drug Discovery Dev., 2007, 10, 654
7. R. Dalpozzo, G. Bartoli, Curr. Org. Synth., 2005, 9, 163
8. S. Cacchi, G. Fabrizi, Chem. Rev., 2005, 105, 2873
9. G. R. Humphrey, J. T. Kuethe, Chem. Rev., 2006, 106, 2875
10. G. W. Gribble, Pure Appl. Chem., 2003, 75, 1417
11. S. Agarwal, S. Cämmerer, S. Filali, W. Froöhner, J. Knöll, M. P. Krahl, K. R. Reddy, H.-J. Knölker, Curr. Org. Chem., 2005, 9, 1601
12. L. Joucla, L. Djakovitch, Adv. Synth. Catal., 2009, 351, 673
13. G. Sartori, R. Maggi, Chem. Rev., 2006, 106, 1077
14. M. Bandini, A. Eichholzer, Angew. Chem., Int. Ed., 2009, 48, 9608
15. R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1970
16. H.-J. Borschberg, Curr. Org. Chem., 2005, 9, 1465
17. C.-G. Yang, G. Liu, B. Jiang, J. Org. Chem., 2002, 67, 9392
18. A. B. Smith III, H. Cui, Org. Lett., 2003, 5, 587
19. M. Kim, E. Vedejs, J. Org. Chem., 2004, 69, 7262
20. K. R. Buszek, N. Brown, D. Luo, Org. Lett., 2009, 11, 201
21. D. A. Brown, M. Mishra, S. Zhang, S. Biswas, I. Parrington, T. Antonio, M. E. A. Reith, A. K. Dutta, Bioorg. Med. Chem., 2009, 17, 3923
22. G.-Y. J. Im, S. M. Bronner, A. E. Goetz, R. S. Paton, P. H.-Y. Cheong, K. N. Houk, N. K. Garg, J. Am. Chem. Soc., 2010, 132, 17933
23. D. S. Carter, H.-Y. Cai, E. K. Lee, P. S. Iyer, M. C. Lucas, R. Roetz, R. C. Schoenfeld, R. J. Weikert, Bioorg. Med. Chem. Lett., 2010, 20, 3941
24. D. W. Robbins, T. A. Boebel, J. F. Hartwig, J. Am. Chem. Soc., 2010, 132, 4068
25. D. Dhanak, C. B. Reese, J. Chem. Soc., Perkin. Trans. 1, 1986, 2181
26. J. Poisson, I. Wharf, D. S. Bohle, M. M. Barsan, Y. Gu, I. S. Butler, J. Organomet. Chem., 2010, 695, 2557
27. J. A. Reichl, D. H. Berry, Adv. Organomet. Chem., 1998, 43, 197
28. Z. Rappaport and Y. Apeloig, The Chemistry of Organic Silicon Compounds, vol. 2, Wiley, New York, 1998
29. F. Kakiuchi, N. Chatani, Adv. Synth. Catal., 2003, 345, 1077
30. F. Kakiuchi, M. Matsumoto, K. Tsuchiya, K. Igi, T. Hayamizu, N. Chatani, S. Murai, J. Organomet. Chem., 2003, 686, 134
31. F. Kakiuchi, K. Tsuchiya, M. Matsumoto, E. Mizushima, N. Chatani, J. Am. Chem. Soc., 2004, 126, 12792
32. B. Lu, J. R. Falck, Angew. Chem., Int. Ed., 2008, 47, 7508
33. H. F. T. Klare, M. Oestreich, J. Ito, H. Nishiyama, Y. Ohki, K. Tatsumi, J. Am. Chem. Soc., 2011, 133, 3312
34. T. Tsuchimoto, Y. Iketani, M. Sekine, Chem. Eur. J., 2012, 18, 9500
35. D. M. Gutsulyak, S. F. Vyboishchikov, G. I. Nikonov, J. Am. Chem. Soc., 2010, 132, 5950
36. J. F. Dunne, S. R. Neal, J. Engelkemier, A. Ellern, A. D. Sadow, J. Am. Chem. Soc., 2011, 133, 16782
37. L. H. Sommer, J. D. Citron, J. Org. Chem., 1967, 32, 2470
38. J. X. Wang, A. K. Dash, J. C. Berthet, M. Ephritikhine, M. S. Eisen, J. Organomet. Chem., 2000, 610, 49
39. W.-D. Wang, R. Eisenberg, Organometallics, 1991, 10, 2222
40. H. Q. Liu, J. F. Harrod, Organometallics, 1992, 11, 822
41. T. Kimura, K. Kamata, N. Mizuno, Angew. Chem., Int. Ed., 2012, 51, 6700
42. Y. Ojima, K. Yamaguchi, N. Mizuno, Adv. Synth. Catal., 2009, 351, 1405
43. R. J. P. Corriu, J. J. E. Moreau, J. Organomet. Chem., 1976, 114, 135
44. I. Ojima, M. Nihonyanagi, Y. Nagai, J. Chem. Soc., Chem. Commun., 1972, 938
45. B. Marciniec, Silicon Chem., 2002, 1, 155
46. S. Díez-González, S. P. Nolan, Org. Prep. Proced. Int., 2007, 39, 523
47. M. P. Doyle, K. G. High, V. Bagheri, R. J. Pieters, P. J. Lewis, M. M. Pearson, J. Org. Chem., 1990, 55, 6082
48. E. Grinenval, J.-M. Basset, F. Lefebvre, Inorg. Chem., 2010, 49, 8749
49. V. K. Dioumaev, R. M. Bullock, Nature, 2003, 424, 530
50. G. Du, P. E. Fanwick, M. M. Abu-Omar, J. Am. Chem. Soc., 2007, 129, 5180
51. D. V. Gutsulyak, S. F. Vyboishchikov, G. I. Nikonov, J. Am. Chem. Soc., 2010, 132, 5950