Double oxidation of α-(alkylideneamino)nitriles to imides by molecular oxygen under mild basic conditions

Chemical Communications

Volumn 50, Issue 92, 2014, Pages 14334-14337

  Zhang, Yu ^a   Pan, Ling ^a   Zou, Yunjia ^a   Xu, Xianxiu ^a   Liu, Qun ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA(ALKYLIDENEAMINO)NITRILE DERIVATIVE; BASE; IMIDE; NITRILE; OXYGEN; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; BUILDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; OXIDATION; ROOM TEMPERATURE;

EID: 84908425539     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc06481j     Document Type: Article

References (60)

1. J. Wang, X. Liu, X. Feng, Chem. Rev. 2011, 111, 6947
2. T. Opatz, Synthesis. 2009, 1941
3. L. Ma, W. Chen, D. Seidel, J. Am. Chem. Soc. 2012, 134, 15305
4. P. Fontaine, A. Chiaroni, G. Masson, J. Zhu, Org. Lett. 2008, 10, 1509
5. I. Schäfer, T. Opatz, Synthesis. 2011, 1691
6. I. Bergner, C. Wiebe, N. Meyer, T. Opatz, J. Org. Chem. 2009, 74, 8243
7. Y. Yamashita, M. Matsumoto, Y.-J. Chen, S. Kobayashi, Tetrahedron. 2012, 68, 7558
8. S. Kobayashi, R. Yazaki, K. Seki, Y. Yamashita, Angew. Chem., Int. Ed. 2008, 47, 5613
9. Y.-J. Chen, K. Seki, Y. Yamashita, S. Kobayashi, J. Am. Chem. Soc. 2010, 132, 3244
10. I. Bergner, T. Opatz, J. Org. Chem. 2007, 72, 7083
11. J.-B. Gualtierotti, X. Schumacher, P. Fontaine, G. Masson, Q. Wang, J. Zhu, Chem. Eur. J. 2012, 18, 14812
12. D. Enders, A. S. Amaya, F. Pierre, New J. Chem. 1999, 261
13. Z. Zhang, Z. Yin, J. F. Kadow, N. A. Meanwell, T. Wang, J. Org. Chem. 2004, 69, 1360
14. S. V. Pawar, V. G. Pawar, W. Dehaen, W. M. De Borggraeve, Org. Lett. 2008, 10, 4473
15. J. Tan, X. Xu, L. Zhang, Y. Li, Q. Liu, Angew. Chem., Int. Ed. 2009, 48, 2868
16. Y. Li, X. Xu, J. Tan, C. Xia, D. Zhang, Q. Liu, J. Am. Chem. Soc. 2011, 133, 1775
17. X. Liu, L. Zhang, X. Xu, S. Wang, L. Pan, Q. Zhang, Q. Liu, Chem. Commun. 2014, 50, 8764
18. Y. Zhang, L. Pan, X. Xu, H. Luo, Q. Liu, Chem. Commun. 2014, 50, 11039
19. X. Xu, L. Zhang, X. Liu, L. Pan, Q. Liu, Angew. Chem., Int. Ed. 2013, 52, 9271
20. Z. Z. Shi, C. Zhang, C. H. Tang, N. Jiao, Chem. Soc. Rev. 2012, 41, 3381
21. W. Q. Wu, H. F. Jiang, Acc. Chem. Res. 2012, 45, 1736
22. A. E. Wendlandt, A. M. Suess, S. S. Stahl, Angew. Chem., Int. Ed. 2011, 50, 11062
23. P. R. Ogilby, Chem. Soc. Rev. 2010, 39, 3181
24. T. Punniyamurthy, S. Velusamy, J. Iqbal, Chem. Rev. 2005, 105, 2329
25. F. Hollmann, I. W. C. E. Arends, K. Buehler, A. Schallmey, B. Bühler, Green Chem. 2011, 13, 226
26. M. M. Hussain, P. J. Walsh, Acc. Chem. Res. 2008, 41, 883
27. L. Zhang, X. Bi, X. Guan, X. Li, Q. Liu, B.-D. Barry, P. Liao, Angew. Chem., Int. Ed. 2013, 52, 11303
28. Y. Li, X. Xu, C. Xia, L. Pan, Q. Liu, Adv. Synth. Catal. 2012, 354, 1712
29. N. Travert, A. Al-Mourabit, J. Am. Chem. Soc. 2004, 126, 10252
30. Q. Lu, J. Zhang, F. Wei, Y. Qi, H. Wang, Z. Liu, A. Lei, Angew. Chem., Int. Ed. 2013, 52, 7156
31. Y.-F. Liang, N. Jiao, Angew. Chem., Int. Ed. 2014, 53, 548
32. J. Zhu and H. Bienaymé, Multicomponent Reactions, Wiley-VCH, Weinheim, 2005
33. D. J. Ramón, M. Yus, Angew. Chem., Int. Ed. 2005, 44, 1602
34. A. Dömling, Chem. Rev. 2006, 106, 17
35. D. Tejedor, F. García-Tellado, Chem. Soc. Rev. 2007, 36, 484
36. A. Dömling, W. Wang, K. Wang, Chem. Rev. 2012, 112, 3083
37. N. Isambert, M. del M. S. Duque, J.-C. Plaquevent, Y. Génisson, J. Rodriguez, T. Constantieux, Chem. Soc. Rev. 2011, 40, 1347
38. M. R. Nahm, J. R. Potnick, P. S. White, J. S. Johnson, J. Am. Chem. Soc. 2006, 128, 2751
39. Y. Shibata, K. Tanaka, J. Am. Chem. Soc. 2009, 131, 12552
40. P. S. Baran, M. P. DeMartino, Angew. Chem., Int. Ed. 2006, 45, 7083
41. K. S. Yang, A. E. Nibbs, Y. E. Turkmen, V. H. Rawal, J. Am. Chem. Soc. 2013, 135, 16050
42. H. Nemoto, T. Kawamura, N. Miyoshi, J. Am. Chem. Soc. 2005, 127, 14546
43. H. Nemoto, Y. Kubota, Y. Yamamoto, J. Org. Chem. 1990, 55, 4515
44. H. Nemoto, X. Li, R. Ma, I. Suzuki, M. Shibuya, Tetrahedron Lett. 2003, 44, 73
45. Y. Zhang, L. Pan, X. Xu, Q. Liu, RSC Adv. 2012, 2, 5138
46. T. Tomizawa, K. Orimoto, T. Niwa, M. Nakada, Org. Lett. 2012, 14, 6294
47. A. Schnyder, A. F. Indolese, J. Org. Chem. 2002, 67, 594
48. Z. Jin, B. Xu, S. G. DiMagno, G. B. Hammond, J. Fluorine Chem. 2012, 143, 226
49. K. C. Nicolaou, C. J. N. Mathison, Angew. Chem., Int. Ed. 2005, 44, 5992
50. R. Ito, N. Umezawa, T. Higuchi, J. Am. Chem. Soc. 2005, 127, 834
51. L. Xu, S. Zhang, M. L. Trudell, Chem. Commun. 2004, 1668
52. D. A. Evans, P. Nagorny, R. Xu, Org. Lett. 2006, 8, 5669
53. J. Sperry, Synthesis. 2011, 3569
54. X. Yan, K. Fang, H. Liu, C. Xi, Chem. Commun. 2013, 49, 10650
55. L. Pan, Q. Liu, Synlett. 2011, 1073
56. L. Pan, X. Bi, Q. Liu, Chem. Soc. Rev. 2013, 42, 1251
57. Q. Liu, 1,1-Bis(organosulfanyl)alk-1-enes (Ketene S, S-Acetals), in Science of Synthesis, Compounds with Four and Three Carbon-Heteroatom Bonds, ed. M. B. Nielsen, Georg Thieme, Stuttgart, 2014, p. 245
58. Y. H. Cho, C.-Y. Lee, D.-C. Ha, C.-H. Cheon, Adv. Synth. Catal. 2012, 354, 2992
59. Y. Liu, X. Yun, D. Zhang-Negrerie, J. Huang, Y. Du, K. Zhao, Synthesis. 2011, 2984
60. L. Pinheiro, D. Buisson, S. Cortial, M. Delaforge, J. Ouazzani, J. Mol. Catal. B: Enzym. 2011, 68, 211