Rh(III)-catalyzed C-H activation and double directing group strategy for the regioselective synthesis of naphthyridinones

Journal of the American Chemical Society

Volumn 135, Issue 39, 2013, Pages 14492-14495

  Huckins, John R ^a   Bercot, Eric A ^a,b   Thiel, Oliver R ^a   Hwang, Tsang Lin ^a   Bio, Matthew M ^a  

^a AMGEN INC   (United States)

^b Suterra LLC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

C-H ACTIVATION; CATALYST LOADINGS; CATALYZED SYNTHESIS; DIRECTING GROUPS; ELEVATED TEMPERATURE; HIGH YIELD; REGIOSELECTIVE SYNTHESIS; ROOM TEMPERATURE;

ACTIVATION ANALYSIS; CATALYST SELECTIVITY; HYDROCARBONS; RHODIUM;

CATALYSIS;

ALKYNE DERIVATIVE; DEUTERIUM; HYDROXYL GROUP; NAPHTHYRIDINE DERIVATIVE; NICOTINAMIDE DERIVATIVE; OXIDE; RHODIUM; TRANSITION ELEMENT;

ANNULATION REACTION; ARTICLE; CATALYSIS; CATALYST; ELECTRON; OXIDATIVE COUPLING; REACTION OPTIMIZATION; REGIOSELECTIVE SYNTHESIS; ROOM TEMPERATURE; STOICHIOMETRY; SYNTHESIS;

CATALYSIS; NAPHTHYRIDINES; NIACINAMIDE; RHODIUM; STEREOISOMERISM;

EID: 84885107598     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja405140f     Document Type: Article

References (35)

1. Bull, J. A.; Mousseau, J. J.; Guillaume, P.; Charrette, A. B. Chem. Rev. 2012, 112, 2642
2. Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications, 3 rd ed.; Wiley-VCH: Weinheim, Germany, 2012.
3. Patureau, F. W.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 1977
4. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
5. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 43, 814
6. Umeda, N.; Tsurgi, H.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2008, 47, 4019
7. Fukutani, T.; Umeda, M.; Hirano, K.; Satoh, T.; Miura, M. Chem. Commun. 2009, 5141
8. Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474
9. Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 3645
10. Hyster, T. K.; Rovis, T. J. Am. Chem. Soc. 2010, 132, 10565
11. Hyster, T. K.; Rovis, T. Chem. Sci. 2011, 2, 1606
12. Guimond, N.; Fagnou, K. J. Am. Chem. Soc. 2009, 131, 12050
13. Rakshit, S.; Grohmann, C.; Besset, T.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2350
14. Wang, H.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 7318
15. Wang, H.; Grohmann, C.; Nimphius, C.; Glorius, F. J. Am. Chem. Soc. 2012, 134, 19592
16. Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908
17. Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 133, 6449
18. Ye, B.; Cramer, N. J. Am. Chem. Soc. 2013, 135, 636
19. Xu, X.; Liu, Y.; Park, C. M. Angew. Chem., Int. Ed. 2012, 51, 9372
20. Song, G.; Gong, X.; Li, X. J. Org. Chem. 2011, 76, 7583
21. Fang, Y.-Q.; Bio, M. M.; Hansen, K. B.; Potter, M. S.; Clausen, A. J. Am. Chem. Soc. 2010, 132, 15525
22. Johnson, D. S.; Chung, C.; Fay, L. K.; Favor, D. A.; Repine, J. T.; White, A. D.; Akunne, H. C.; Fitzgerald, L.; Nicholls, K.; Snyder, B. J.; Whetzel, S. Z.; Zhang, L.; Serpa, K. A. Bioorg. Med. Chem. Lett. 2011, 21, 2621
23. Siu, T.; Kozina, E. S.; Jung, J.; Altman, M. D.; Rush, T.; Dinsmore, C. J.; Young, J. R.; Rosenstein, C.; Chan, G.; Mathur, A.; Bachman, E.; Mo, J.-R.; Xu, L.; Bouthillette, M.; Marshall, C. G. Bioorg. Med. Chem. Lett. 2010, 20, 7421
24. Li, Y.; Rossi, M. A.; Liang, J.; Siu, T.; Hu, E.; Cosford, N.; Prasit, P.; Barnett, S. F.; Defeo-Jones, D.; Jones, R. E.; Robinson, R. G.; Leander, K.; Huber, H. E.; Mittal, S. Bioorg. Med. Chem. Lett. 2009, 19, 834
25. Cho, S. H.; Hwang, S. J.; Chang, S. J. Am. Chem. Soc. 2008, 130, 9254
26. Campeau, L.-C.; Rousseaux, S.; Fagnou, K. J. Am. Chem. Soc. 2005, 127, 1820
27. Kanyiva, K. S.; Nako, Y.; Hiyama, T. Angew. Chem., Int. Ed. 2007, 46, 8872
28. Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 7094
29. Mochida, S.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 5776
30. Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2007, 9, 1407
31. Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9982
32. Patureau, F. W.; Besset, T. Angew. Chem., Int. Ed. 2010, 50, 1064
33. Tsai, A. S.; Brasse, M.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2011, 13, 540
34. Aoyagi, Y.; Abe, T.; Ohta, A. Synthesis 1997, 891
35. After completion of this research, a single example of regioselective functionalization of a nicotinamide was reported in closely related chemistry: Presset, M.; Oehlreich, D.; Rombouts, F.; Molander, G. A. Org. Lett. 2013, 15, 1528