Syntheses of Nitrogen-Containing Heterocycles via Palladium-Catalyzed Intramolecular Dehydrogenative C-H Amination

Synlett

Volumn 26, Issue 18, 2015, Pages 2505-2511

  Nack, William A ^a   Chen, Gong ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

cyclization; heterocycles; metallacycles; nitrogen; palladium

Indexed keywords

AZETIDINE DERIVATIVE; BETA LACTAM; CARBAZOLE DERIVATIVE; CINNAMIC ACID; HETEROCYCLIC COMPOUND; NITROGEN CONTAINING HETEROCYCLE; OXINDOLE; PALLADIUM; PHENYLACETIC ACID; PICOLINIC ACID; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; CROSS COUPLING REACTION; CYCLIZATION; CYCLOPALLADATION; HYDROGEN BOND; METALLATION DEPROTONATION MECHANISM; PALLADIUM CATALYZED INTRAMOLECULAR DEHYDROGENATIVE C H AMINATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 84946490133     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0034-1381051     Document Type: Article

References (35)

1. Joule J. A., Mills K. Heterocyclic Chemistry. 4th ed. Blackwell Oxford: 2000
2. Thansandote P., Lautens M. Chem. Eur. J.: 2009; 15 5874
3. Mei T. S., Kou L., Ma S., Engle K. M., Yu J.-Q. Synthesis: 2012; 44 1778
4. Jeffrey J. L., Sarpong R. Chem. Sci.: 2013; 4 4092
5. Zalatan D. N., Du Bois J. Top. Curr. Chem.: 2010; 292 347
6. Lu H.-J, Zhang X. P. Chem. Soc. Rev.: 2011; 40 1899
7. McIntosh J. A., Coelho P. S., Farwell C. C., Wang Z. J., Lewis J. C., Brown T. R., Arnold F. H. Angew. Chem. Int. Ed.: 2013; 52 9309
8. Louillat M.-L, Patureau F. W. Chem. Soc. Rev.: 2014; 43 901
9. Chen X., Engle K. M., Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed.: 2009; 48 5094
10. Lyons T. W., Sanford M. S. Chem. Rev.: 2010; 110 1147
11. Tsang P. W. C, Zheng N., Buchwald S. L. J. Am. Chem. Soc.: 2005; 127 14560
12. Tsang P. W. C, Munday R. H., Brasche G., Zheng N., Buchwald S. L. J. Org. Chem.: 2008; 73 7603
13. Jordan-Hore J. A., Johansson C. C. C, Guilas M., Beck E. M., Gaunt M. J. J. Am. Chem. Soc.: 2008; 130 16184
14. Wasa M., Yu J.-Q. J. Am. Chem. Soc.: 2008; 130 14058
15. Miura T., Ito Y., Murakami M. Chem. Lett.: 2009; 38 328
16. Mei T.-S, Wang X., Yu J.-Q. J. Am. Chem. Soc.: 2009; 131 10806
17. Nadres E. T., Daugulis O. J. Am. Chem. Soc.: 2012; 134 7
18. He G., Zhao Y., Zhang S., Lu C., Chen G. J. Am. Chem. Soc.: 2012; 134 3
19. He G., Lu C., Zhao Y., Nack W. A., Chen G. Org. Lett.: 2012; 14 2944
20. Ye X., He Z., Ahmed T., Weise K., Akhmedov N. G., Peterson J. L., Shi X. Chem. Sci.: 2013; 4 3712
21. Mei T. S., Leow D., Xiao H., Laforteza B. N., Yu J.-Q. Org. Lett.: 2013; 15 3058
22. Wang C., Chen C., Zhang J., Han J., Wang Q., Guo K., Liu P., Guan M., Yao Y., Zhao Y. Angew. Chem. Int. Ed.: 2014; 53 9884
23. He Y.-P, Zhang C., Fan M., Wu Z., Ma D. Org. Lett.: 2015; 17 496
24. He G., Zhang S.-Y, Nack W. A., Li Q., Chen G. Angew. Chem. Int. Ed.: 2013; 125 11330
25. Li H., Li B.-J, Shi Z.-J. Catal. Sci. Technol.: 2011; 1 191
26. Lapointe D., Fagnou K. Chem. Lett.: 2010; 39 1118
27. Neumann J. J., Rakshit S., Droge T., Glorius F. Angew. Chem. Int. Ed.: 2009; 48 6892
28. Li Q., Zhang S.-Y, He G., Nack W. A., Chen G. Adv. Synth. Catal.: 2014; 356 1544
29. Sun W.-W, Cao P., Mei R.-Q, Li Y., Ma Y.-L, Wu B. Org. Lett.: 2014; 16 480
30. Zhang Q., Chen K., Rao W., Zhang Y., Chen F.-J, Shi B.-F. Angew. Chem. Int. Ed.: 2013; 52 13588
31. Wang Z., Ni J., Kuninobu Y., Kanai M. Angew. Chem. Int. Ed.: 2014; 53 3496
32. Wu X.-S, Zhao Y., Zhang G.-W, Ge H.-B. Angew. Chem. Int. Ed.: 2014; 53 3706
33. Wu X.-S, Yang K., Zhao Y., Sun H., Li G., Ge H.-B. Nat. Commun.: 2015; 6 6462
34. For a recent review on β-lactam synthesis via metal-catalyzed intramolecular C-H amination, see: Zhang Q., Chen K., Shi B. F. Synlett.: 2014; 25 1941
35. McNally A., Haffemayer B., Collins B. S. L, Gaunt M. J. Nature: 2014; 510 129