Palladium-catalyzed cascade process consisting of isocyanide insertion and benzylic C(sp3)-H activation: Concise synthesis of indole derivatives

Organic Letters

Volumn 14, Issue 16, 2012, Pages 4270-4273

  Nanjo, Takeshi ^a   Tsukano, Chihiro ^a   Takemoto, Yoshiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; INDOLE DERIVATIVE; NITRILE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKYNES; CATALYSIS; INDOLES; MOLECULAR STRUCTURE; NITRILES; PALLADIUM;

EID: 84865264744     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302035j     Document Type: Article

References (64)

1. Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902
2. Li, H.; Li, B.-J.; Shi, Z.-J. Catal. Sci. Technol. 2011, 1, 191
3. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885
4. Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976
5. Ackermann, L. Chem. Rev. 2011, 111, 1315
6. Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654
7. Martin, N.; Pierre, C.; Davi, M.; Jazzar, R.; Baudoin, O. Chem.-Eur. J. 2012, 18, 4480
8. Saget, T.; Lemouzy, S. J.; Cramer, N. Angew. Chem., Int. Ed. 2012, 51, 2238
9. Rousseaux, S.; Liégault, B.; Fagnou, K. Chem. Sci. 2012, 3, 244
10. Pan, J.; Su, M.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 8647
11. Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. Angew. Chem., Int. Ed. 2011, 50, 7438
12. Renaudat, A.; Jean-Gérard, L.; Jazzar, R.; Kefalidis, C. E.; Clot, E.; Baudoin, O. Angew. Chem., Int. Ed. 2010, 49, 7261
13. Rousseaux, S.; Davi, M.; Sofack-Kreutzer, J.; Pierre, C.; Kefalidis, C. E.; Clot, E.; Fagnou, K.; Baudoin, O. J. Am. Chem. Soc. 2010, 132, 10706
14. Rousseaux, S.; Gorelsky, S. I.; Chung, B. K.W.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 10692
15. Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 9886
16. Chaumontet, M.; Piccardi, R.; Audic, N.; Hitce, J.; Peglion, J.-L.; Clot, E.; Baudoin, O. J. Am. Chem. Soc. 2008, 130, 15157
17. Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2008, 10, 1759
18. Campeau, L.-C.; Schipper, D. J.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3266
19. Lafrance, M.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 14570
20. Ren, H.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 3462
21. Dong, C.-G.; Hu, Q.-S. Angew. Chem., Int. Ed. 2006, 45, 2289
22. Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685
23. Baudoin, O.; Herrbach, A.; Guéritte, F. Angew. Chem., Int. Ed. 2003, 42, 5736
24. Cattelani, M.; Motti, E.; Ghelli, S. Chem. Commun. 2000, 2003
25. For recent work in our laboratory, see: Tsukano, C.; Okuno, M.; Takemoto, Y. Angew. Chem., Int. Ed. 2012, 51, 2763
26. Novák, P.; Correa, A.; Gallardo-Donaire, J.; Martin, R. Angew. Chem., Int. Ed. 2011, 50, 12236
27. Liégault, B.; Fagnou, K. Organometallics 2008, 27, 4841
28. Wang, D.-H.; Wasa, M.; Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 7190
29. Delcamp, J. H.; White, M. C. J. Am. Chem. Soc. 2006, 128, 15076
30. Iglesias, á.; álvarez, R.; de Lera, á. R.; Muñiz, K. Angew. Chem., Int. Ed. 2012, 51, 2225
31. He, G.; Zhao, Y.; Zhang, S.; Lu, C.; Chen, G. J. Am. Chem. Soc. 2012, 134, 3
32. Ano, Y.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 12984
33. He, G.; Chen, G. Angew. Chem., Int. Ed. 2011, 50, 5192
34. Feng, Y.; Wang, Y.; Landgraf, B.; Liu, S.; Chen, G. Org. Lett. 2010, 12, 3414
35. Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965
36. Giri, R.; Maugel, N.; Li, J.-J.; Wang, D.-H.; Breazzano, S. P.; Saunders, L. B.; Yu, J.-Q. J. Am. Chem. Soc. 2007, 129, 3510
37. Zaitsev, V. G.; Shaboshov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154
38. For a recent review on the Pd-catalyzed cascade reaction, see: Vlaar, T.; Ruijter, E.; Orru, R. V. A. Adv. Synth. Catal. 2011, 353, 809
39. Wang, Y.; Wang, H.; Peng, J.; Zhu, Q. Org. Lett. 2011, 13, 4604
40. Tobisu, M.; Imoto, S.; Ito, S.; Chatani, N. J. Org. Chem. 2010, 75, 4835
41. Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215
42. Hsu, G. C.; Kosar, W. P.; Jones, W. D. Organometallic 1994, 13, 385
43. Jones, W. D.; Kosar, W. P. J. Am. Chem. Soc. 1986, 108, 5640
44. Mei, T.-S.; Kou, L.; Ma, S.; Engle, K. M.; Yu, J.-Q. Synthesis 2012, 44, 1778
45. Taber, D. F.; Tirunahari, P. K. Tetrahedron 2011, 67, 7195
46. Cacchi, S.; Fabrizi, G. Chem. Rev. 2011, 111, DOI: 10.1021/cr100403z.
47. Song, J. J.; Reeves, J. T.; Fandrick, D. R.; Tan, Z.; Yee, N. K.; Senanayake, C. H. ARKIVOC 2010, 390
48. Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875
49. Seong, C. M.; Park, C. M.; Choi, J.; Park, N. S. Tetrahedron Lett. 2009, 50, 1029
50. Lee, S.; Lee, W.-M.; Sulikowski, G. A. J. Org. Chem. 1999, 64, 4224
51. Tokuyama, H.; Yamashita, T.; Reding, M. T.; Kaburagi, Y.; Fukuyama, T. J. Am. Chem. Soc. 1999, 121, 3791
52. Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468
53. Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127
54. Ito, Y.; Kobayashi, K.; Seko, N.; Saegusa, T. Bull. Chem. Soc. Jpn. 1984, 57, 73
55. Houlihan, W. J.; Parrino, V. A.; Uike, Y. J. Org. Chem. 1981, 46, 4511
56. Ito, Y.; Kobayashi, K.; Saegusa, T. J. Am. Chem. Soc. 1977, 99, 3532
57. Jones, C. D. J. Org. Chem. 1972, 37, 3624
58. Onitsuka, K.; Suzuki, S.; Takahashi, S. Tetrahedron Lett. 2002, 43, 6197
59. Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153
60. Yamamoto, Y. Coord. Chem. Rev. 1980, 32, 193
61. Baelen, G. V.; Kuijer, S.; Rýček, L.; Sergeyev, S.; Janssen, E.; de Kanter, F. J. J.; Maes, B. U. W.; Ruijter, E.; Orru, R. V. A. Chem.-Eur. J. 2011, 17, 15039
62. Vlaar, T.; Ruijter, E.; Znabet, A.; Janssen, E.; de Kanter, F. J. J.; Maes, B. U. W.; Orru, R. V. A. Org. Lett. 2011, 13, 6496
63. Schmidt, A. W.; Reddy, K. R.; Knölker, H.-J. Chem. Rev. 2012, 112, 3193
64. Janosik, T.; Wahlström, N.; Bergman, J. Tetrahedron 2008, 64, 9159