Pd-catalyzed sequential C-C and C-N bond formations for the synthesis of N-heterocycles: Exploiting protecting group-directed C-H activation under modified reaction conditions

Chemistry - An Asian Journal

Volumn 6, Issue 8, 2011, Pages 1952-1957

  Kim, Byung Seok ^a   Lee, Sun Young ^b   Youn, So Won ^a  

^a Hanyang University   (South Korea)

^b Pukyong National University   (South Korea)

Author keywords

C H activation; domino reactions; heterocycles; olefins; palladium

Indexed keywords

ACTIVATED OLEFINS; BOND FORMATION; C-H ACTIVATION; DOMINO REACTIONS; HETEROCYCLES; N-HETEROCYCLES; OLEFINATION; REACTION CONDITIONS;

ACTIVATION ANALYSIS; ADDITION REACTIONS; CATALYSIS; FUNCTIONAL GROUPS; OLEFINS; REACTION KINETICS;

SYNTHESIS (CHEMICAL);

EID: 79961078838     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201100024     Document Type: Article

References (80)

1. A. E. Shilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879
2. G. Dyker, Angew. Chem. 1999, 111, 1808
3. Angew. Chem. Int. Ed. 1999, 38, 1698
4. C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633
5. F. Kakiuchi, S. Murai, Acc. Chem. Res. 2002, 35, 826
6. V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731
7. K. Godula, D. Sames, Science 2006, 312, 67
8. E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318
9. M. Zhang, Adv. Synth. Catal. 2009, 351, 2243.
10. I. Moritanl, Y. Fujiwara, Tetrahedron Lett. 1967, 8, 1119
11. Y. Fujiwara, I. Moritani, S. Danno, R. Asano, S. Teranishi, J. Am. Chem. Soc. 1969, 91, 7166
12. Y. Fujiwara, R. Asano, I. Moritani, S. Teranishi, J. Org. Chem. 1976, 41, 1681
13. Y. Fujiwara, O. Maruyama, M. Yoshidomi, H. Taniguchi, J. Org. Chem. 1981, 46, 851
14. C. Jia, W. Lu, T. Kitamura, Y. Fujiwara, Org. Lett. 1999, 1, 2097
15. C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, Y. Fujiwara, Science 2000, 287, 1992. For selected examples of olefination of arenes, see
16. E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2003, 125, 9578
17. S. H. Cho, S. J. Hwang, S. Chang, J. Am. Chem. Soc. 2008, 130, 9254
18. J. Wu, X. Cui, L. Chen, G. Jiang, Y. Wu, J. Am. Chem. Soc. 2009, 131, 13888
19. X. Zhang, S. Fan, C.-Y. He, X. Wan, Q.-Q. Min, J. Yang, Z.-X. Jiang, J. Am. Chem. Soc. 2010, 132, 4506.
20. R. F. Heck, Acc. Chem. Res. 1979, 12, 146
21. I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009
22. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4516
23. Angew. Chem. Int. Ed. 2005, 44, 4442.
24. J.-Q. Yu, R. Giri, X. Chen, Org. Biomol. Chem. 2006, 4, 4041
25. O. Daugulis, V. G. Zaitzev, D. Shabashov, Q.-N. Pham, A. Lazareva, Synlett 2006, 3382
26. B.-J. Li, S.-D. Yang, Z.-J. Shi, Synlett 2008, 949
27. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
28. Angew. Chem. Int. Ed. 2009, 48, 5094
29. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
30. R. Jazzar, J. Hitce, A. Renaudat, J. Sofack-Kreutzer, O. Baudoin, Chem. Eur. J. 2010, 16, 2654.
31. B.-F. Shi, Y.-H. Zhang, J. K. Lam, D.-H. Wang, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 460
32. D.-H. Wang, K. M. Engle, B.-F. Shi, J.-Q. Yu, Science 2010, 327, 315
33. Y.-H. Zhang, B.-F. Shi, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 5072.
34. B. S. Kim, C. Jang, D. J. Lee, S. W. Youn, Chem. Asian J. 2010, 5, 2336.
35. M. Miura, T. Tsuda, T. Satoh, S. Pivsa-Art, M. Nomura, J. Org. Chem. 1998, 63, 5211
36. N. Della Cá, E. Motti, M. Catellani, Adv. Synth. Catal. 2008, 350, 2513.
37. M. Wasa, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 3680
38. J.-J. Li, T.-S. Mei, J.-Q. Yu, Angew. Chem. 2008, 120, 6552
39. Angew. Chem. Int. Ed. 2008, 47, 6452.
40. K. Ueura, T. Satoh, M. Miura, Org. Lett. 2007, 9, 1407
41. F. Wang, G. Song, X. Li, Org. Lett. 2010, 12, 5430
42. F. W. Patureau, T. Besset, F. Glorius, Angew. Chem. 2011, 123, 1096
43. Angew. Chem. Int. Ed. 2011, 50, 1064.
44. L. F. Tietze, Chem. Rev. 1996, 96, 115
45. E. Negishi, C. Copéret, S. Ma, S. Y. Liou, F. Liu, Chem. Rev. 1996, 96, 365
46. R. Grigg, V. Sridharan, J. Organomet. Chem. 1999, 576, 65
47. J. Montgomery, Angew. Chem. 2004, 116, 3980
48. Angew. Chem. Int. Ed. 2004, 43, 3890
49. T. Miura, M. Murakami, Chem. Commun. 2007, 217
50. S. W. Youn, Eur. J. Org. Chem. 2009, 2597. For selected examples, see
51. S. W. Youn, J.-H. Song, D.-I. Jung, J. Org. Chem. 2008, 73, 5658
52. J. O. Park, S. W. Youn, Org. Lett. 2010, 12, 2258.
53. S. J. Pastine, S. W. Youn, D. Sames, Org. Lett. 2003, 5, 1055
54. S. J. Pastine, S. W. Youn, D. Sames, Tetrahedron 2003, 59, 8859
55. S. W. Youn, S. J. Pastine, D. Sames, Org. Lett. 2004, 6, 581
56. S. W. Youn, J. I. Eom, Org. Lett. 2005, 7, 3355
57. S. W. Youn, J. Org. Chem. 2006, 71, 2521
58. S. W. Youn, Org. Prep. Proced. Int. 2006, 38, 505
59. S. W. Youn, J. I. Eom, J. Org. Chem. 2006, 71, 6705
60. S. W. Youn, Synlett 2007, 3050
61. S. W. Youn, J. H. Bihn, Tetrahedron Lett. 2009, 50, 4598
62. S. K. Ock, S. W. Youn, Bull. Korean Chem. Soc. 2010, 31, 704.
63. M. Balasubramanian, J. G. Keay, in Comprehensive Heterocyclic Chemistry II, Vol. 5 (Eds.:, A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon Press, Oxford, New York, 1996, p. 245
64. A. J. Molinari, M. A. Ashwell, B. H. Ridgway, A. A. Failli, W. J. Moore, PCT Int. Appl. WO 2004050631A1, 2004
65. S. Pegoraro, M. Lang, J. Feurle, J. Krauss, PCT Int. Appl. WO 2005105752A1, 2005
66. B. H. Ridgway, W. J. Moore, M. A. Ashwell, W. R. Solvibile, A. T.-T. Lee, M. E. Hoke, M. Antane, A. A. Failli, PCT Int. Appl. WO 2006009831A1, 2006
67. G. Beke, É. Bozó, G. Czíra, J. Éles, S. Farkas, K. Hornok, É. Schmidt, É. Szentirmay, I. Vágó, M. Vastag, PCT Int. Appl. WO 2007072092A2, 2007
68. K. R. Shaw, M. Zhang, PCT Int. Appl. WO 2008016596A2, 2008
69. J. Fotie, D. S. Bohle, M. Olivier, M. A. Gomez, S. Nzimiro, J. Nat. Prod. 2007, 70, 1650.
70. M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de Vries, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen, J. Am. Chem. Soc. 2002, 124, 1586.
71. I. V. Seregin, V. Ryabova, V. Gevorgyan, J. Am. Chem. Soc. 2007, 129, 7742
72. B. S. Lane, M. A. Brown, D. Sames, J. Am. Chem. Soc. 2005, 127, 8050
73. H. A. Chiong, O. Daugulis, Org. Lett. 2007, 9, 1449.
74. K. Muñiz, Angew. Chem. 2009, 121, 9576
75. III catalytic cycle, see
76. D. C. Powers, T. Ritter, Nat. Chem. 2009, 1, 302
77. IV catalytic cycle, see
78. C. F. Rosewall, P. A. Sibbald, D. V. Liskin, F. E. Michael, J. Am. Chem. Soc. 2009, 131, 9488
79. G.-W. Wang, T.-T. Yuan, X.-L. Wu, J. Org. Chem. 2008, 73, 4717
80. L. V. Desai, H. A. Malik, M. S. Sanford, Org. Lett. 2006, 8, 1141.