Rh-catalyzed oxidative coupling between primary and secondary benzamides and alkynes: Synthesis of polycyclic amides

Journal of Organic Chemistry

Volumn 75, Issue 21, 2010, Pages 7487-7490

  Song, Guoyong ^a   Chen, Dan ^a   Pan, Cheng Ling ^a   Crabtree, Robert H ^c   Li, Xingwei ^a,b  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

^c YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZAMIDES; C-H ACTIVATION; EFFICIENT CATALYSTS; FACILE SYNTHESIS; HETEROCYCLES; HIGH YIELD; OXIDATIVE COUPLINGS; TRICYCLIC PRODUCTS;

ACTIVATION ANALYSIS; AMIDES; RHODIUM;

ACETYLENE;

ALKYNE; AMIDE; BENZAMIDE; ISOQUINOLINE DERIVATIVE;

ARTICLE; BIOSYNTHESIS; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION KINETICS; REACTION OPTIMIZATION;

ALKYNES; BENZAMIDES; CATALYSIS; OXIDATION-REDUCTION; POLYCYCLIC COMPOUNDS; RHODIUM;

EID: 78049513726     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101596d     Document Type: Article

References (41)

1. For leading reviews, see: Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
2. Sun, C.-L.; Shi, Z.-J. Chem. Commun. 2010, 46, 677
3. Chen, X.; Engle, K. M.; Wang, D. H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
4. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
5. Xu, L.-M.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712
6. Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013
7. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 3013
8. Satoh, T.; Miura, M. Top. Organomet. Chem. 2008, 24, 61
9. Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731
10. Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826
11. Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698
12. For selected examples, see: Abet, V.; Nunez, A.; Mendicuti, F.; Burgos, C.; Alvarez-Builla, J. J. Org. Chem. 2008, 73, 8800
13. Ahmed, E.; Briseno, A. L.; Xia, Y.; Jenekhe, S. A. J. Am. Chem. Soc. 2008, 130, 1118
14. Parenty, A. D. C.; Song, Y.-F.; Richmond, C. J.; Cronin, L. Org. Lett. 2007, 9, 2253
15. Barrio, J. R.; Sattsangi, P. D.; Gruber, B. A.; Dammann, L. G.; Leonard, N. J. J. Am. Chem. Soc. 1976, 98, 7408
16. Le, T. N.; Gang, S. G.; Cho, W.-J. J. Org. Chem. 2004, 69, 2768
17. Ruchelman, A. L.; Houghton, P. J.; Zhou, N.; Liu, A.; Liu, L. F.; LaVoie, E. J. J. Med. Chem. 2005, 48, 792
18. Miura, T.; Yamaushi, M.; Murakami, M. Org. Lett. 2008, 10, 3085
19. Kajita, Y.; Matsubara, S.; Kurahashi, T. J. Am. Chem. Soc. 2008, 130, 6058
20. Guimond, N.; Fagnou, K. J. Am. Chem. Soc. 2009, 131, 12050
21. Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474
22. Fukutani, T.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. Chem. Commun. 2009, 5141
23. Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 7094
24. Ueura, K.; Satoh, T.; Miura, M. J. Org. Chem. 2007, 72, 5362
25. Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2007, 9, 1407
26. Mochida, S.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 6295
27. Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 2068
28. Uto, T.; Shimizu, M.; Ueura, K.; Tsurugi, H.; Satoh, T.; Miura, M. J. Org. Chem. 2008, 73, 298
29. Umeda, N.; Tsurugi, H.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2008, 47, 4019
30. Mochida, S.; Shimizu, M.; Hirano, K.; Satoh, T.; Miura, M. Chem. Asian J. 2010, 5, 847
31. Li, L.; Brennessel, W. W.; Jones, W. D. J. Am. Chem. Soc. 2008, 130, 12414
32. Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9982
33. Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9585
34. Li, B.-J.; Tian, S.-L.; Fang, Z.; Shi, Z.-J. Angew. Chem., Int. Ed. 2008, 47, 1115
35. Wan, X.; Ma, Z.; Li., B.; Zhang, K.; Cao, S.; Zhang, S.; Shi., Z. J. Am. Chem. Soc. 2006, 128, 7416
36. Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P.W. N. M. J. Am. Chem. Soc. 2002, 124, 1586
37. Giri, R.; Lam, J. K.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 686
38. During the preparation of this manuscript, similar studies leading to isoquinolone synthesis catalyzed by Rh(III) were reported by the groups of T. Rovis and M. Miura; see: Hyster, T. K.; Rovis, T. J. Am. Chem. Soc. 2010, 132, 10565
39. Mochida, S.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. Chem. Lett. 2010, 39, 744
40. Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908
41. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147