Aerobic oxidative Mannich reaction promoted by catalytic amounts of stable radical cation salt

Journal of Organic Chemistry

Volumn 79, Issue 20, 2014, Pages 9860-9864

  Huo, Congde ^a   Wu, Mingxia ^a   Jia, Xiaodong ^a   Xie, Haisheng ^a   Yuan, Yong ^a   Tang, Jing ^a  

^a NORTHWEST NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; KETONES; OXIDANTS;

CATALYTIC AMOUNTS; CHEMICAL EQUATIONS; CHEMICAL OXIDANTS; CYCLIZED PRODUCTS; MANNICH REACTIONS; NEUTRAL CONDITIONS; STABLE RADICALS; TERMINAL OXIDANTS;

CHEMICAL REACTIONS;

ACETONE; ACID; BASE; CATION; KETONE DERIVATIVE; METAL; OXIDIZING AGENT; RADICAL; SODIUM CHLORIDE; TERTIARY AMINE; TETRAHYDROISOQUINOLINE DERIVATIVE;

AEROBIC OXIDATIVE MANNICH REACTION; AIR; ARTICLE; CATALYSIS; COVALENT BOND; MANNICH REACTION; OXIDATIVE COUPLING; STOICHIOMETRY; THIN LAYER CHROMATOGRAPHY;

EID: 84908245524     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5017822     Document Type: Article

References (42)

1. (a) Kleinman, E. D. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 893.
2. (b) Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044.
3. (c) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
4. (d) Ting, A.; Schaus, S. E. Eur. J. Org. Chem. 2007, 5797.
5. (e) Verkade, J. M. M.; van Hemert, L. J. C.; Quaedflieg, P. J. L. M.; Rutjes, F. P. J. T. Chem. Soc. Rev. 2008, 37, 29-41.
6. Murahashi, S.; Komiya, N.; Terai, H.; Nakae, T. J. Am. Chem. Soc. 2003, 125, 15312.
7. (a) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810.
8. (b) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
9. (a) Murahashi, S.; Zhang, D. Chem. Soc. Rev. 2008, 37, 1490.
10. (b) Li, C.-J. Acc. Chem. Res. 2009, 42, 335.
11. (c) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
12. (d) Klussmann, M.; Sureshkumar, D. Synthesis 2011, 3, 353.
13. (e) Girard, S. A.; Knauber, T.; Li, C.-J. Angew. Chem., Int. Ed. 2014, 53, 74.
14. (a) Shen, Y.; Li, M.; Wang, S.; Zhan, T.; Tan, Z.; Guo, C. Chem. Commun. 2009, 953.
15. (b) Sud, A.; Sureshkumar, D.; Klussmann, M. Chem. Commun. 2009, 3169.
16. (c) Shu, X.; Yang, Y.; Xia, X.; Ji, K.; Liu, X.; Liang, Y. Org. Biomol. Chem. 2010, 8, 4077.
17. (d) Zeng, T.; Song, G.; Moores, A.; Li, C. Synlett. 2010, 13, 2002.
18. (e) Xie, J.; Li, H.; Zhou, J.; Cheng, Y.; Zhu, C. Angew. Chem., Int. Ed. 2012, 51, 1252.
19. (f) Rueping, M.; Vila, C.; Koenigs, R.; Poscharny, K.; Fabry, D. Chem. Commun. 2011, 47, 2360.
20. (g) Cherevatskaya, M.; Neumann, M.; Fuldner, S.; Harlander, C.; Kummel, S.; Dankesreiter, S.; Pfitzner, A.; Zeitler, K.; Kc¸nig, B. Angew. Chem., Int. Ed. 2012, 51, 4062.
21. (h) Rueping, M.; Zoller, J.; Fabry, D.; Poscharny, K.; Koenigs, M.; Mayer, E. W. Chem. - Eur. J. 2012, 18, 3478.
22. (i) Xue, Q.; Xie, J.; Jin, H.; Cheng, Y.; Zhu, C. Org. Biomol. Chem. 2013, 11, 1606.
23. (j) To, W.; Liu, Y.; Lau, T.; Che, C. Chem. - Eur. J. 2013, 19, 5654.
24. (k) Pan, Y.; Kee, C.; Chen, L.; Tan, C. Green Chem. 2011, 13, 2682.
25. (l) Liu, Q.; Li, Y.; Zhang, H.; Chen, B.; Tung, C.; Wu, L. Chem. - Eur. J. 2012, 18, 620.
26. (m) Mohlmann, L.; Baar, M.; Rie, J.; Antonietti, M.; Wang, X.; Blechert, S. Adv. Synth. Catal. 2012, 354, 1909.
27. (n) Wang, S.; Nai, C.; Jiang, X.; Pan, Y.; Tan, C.; Nesladek, M.; Xu, Q.; Loh, K. P. J. Phys. Chem. Lett. 2012, 3, 2332.
28. (o) Alagiri, K.; Devadig, P.; Prabhu, R. Chem. - Eur. J. 2012, 18, 5160.
29. (p) Dhineshkumar, J.; Lamani, M.; Alagiri, K.; Prabhu, R. Org. Lett. 2013, 15, 1092.
30. (q) Nobuta, T.; Tada, N.; Fujiya, A.; Kariya, A.; Miura, T.; Itoh, A. Org. Lett. 2013, 15, 574.
31. (a) Huo, C.; Xu, X.; An, J.; Jia, X.; Wang, X.; Wang, C. J. Org. Chem. 2012, 77, 8310.
32. (b) Huo, C.; Kang, L.; Xu, X.; Jia, X.; Wang, X.; Yuan, Y.; Xie, H. Tetrahedron. 2014, 70, 1055.
33. (c) Huo, C.; Wang, C.; Wu, M.; Jia, X.; Xie, H.; Yuan, Y. Adv. Synth. Catal. 2014, 356, 411.
34. (d) Huo, C.; Wang, C.; Sun, C.; Jia, X.; Wang, X.; Chang, W.; Wu, M. Adv. Synth. Catal. 2013, 355, 1911.
35. (e) Huo, C.; Wang, C.; Wu, M.; Jia, X.; Wang, X.; Yuan, Y.; Xie, H. Org. Biomol. Chem. 2014, 12, 3123.
36. (a) Nelsen, S. F. Acc. Chem. Res. 1987, 20, 269.
37. (b) Bauld, N. L. Tetrahedron 1989, 45, 5307.
38. (c) Schmittel, M.; Burghart, A. Angew. Chem., Int. Ed. 1997, 36, 2550.
39. (a) Zhang, G.; Wang, S.; Ma, Y.; Kong, W.; Wang, R. Adv. Synth. Catal. 2013, 355, 874.
40. (b) Nie, S.-Z.; Sun, X.; Wei, W.-T.; Zhang, X.-J.; Yan, M.; Xiao, J.-L. Org. Lett. 2013, 15, 2394.
41. (c) Neel, A. J.; Hehn, J. P.; Tripet, P. F.; Toste, F. D. J. Am. Chem. Soc. 2013, 135, 14044.
42. (d) Barton, D. H.; Nakanishi, K.; Meth-Cohn, O. Comprehensive Natural Chemistry; Elsevier: Oxford, U.K., 1999; Vols. 1-9.