Transition-metal-free oxidative α-C-H amination of ketones via a radical mechanism: Mild synthesis of α-amino ketones

Journal of Organic Chemistry

Volumn 79, Issue 18, 2014, Pages 8750-8756

  Jiang, Qing ^a   Xu, Bin ^a   Zhao, An ^a   Jia, Jing ^a   Liu, Tian ^a   Guo, Cancheng ^a  

^a HUNAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; AMINES; AMMONIUM IODIDE; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL); TRANSITION METALS;

CROSS-COUPLINGS; MECHANISTIC STUDIES; ONE STEP SYNTHESIS; PHARMACEUTICAL AGENTS; RADICAL MECHANISM; RADICAL PATHWAY; REACTION PROCESS; SODIUM PERCARBONATE;

KETONES;

AMFEPRAMONE; AMIDE; AMMONIUM DERIVATIVE; ANILINE DERIVATIVE; AROMATIC COMPOUND; KETONE DERIVATIVE; OXIDIZING AGENT; SODIUM DERIVATIVE; TRANSITION ELEMENT;

AMINATION; ARTICLE; CATALYST; CROSS COUPLING REACTION; OXIDATION; RADICAL RESECTION; REACTION ANALYSIS; SYNTHESIS;

EID: 84907975478     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5015855     Document Type: Article

References (72)

1. For recent reviews on functionalization of C-H bonds, see: (a) Li, B.; Dixneuf, P. H. Chem. Soc. Rev. 2013, 42, 5744.
2. (b) Wencel-Delord, J.; Glorius, F. Nat. Chem. 2013, 5, 369.
3. (c) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960.
4. (d) Xu, L.-M.; Li, B.-J.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712.
5. (e) Ackermann, L. Chem. Commun. 2010, 46, 4866.
6. (f) Ackermann, L. Chem. Rev. 2011, 111, 1315.
7. (g) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624.
8. (h) Sehnal, P.; Taylor, R. J. K.; Fairlamb, I. J. S. Chem. Rev. 2010, 110, 824.
9. (i) McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885.
10. (j) Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902.
11. (k) Li, B.-J.; Shi, Z.-J. Chem. Soc. Rev. 2012, 41, 5588.
12. (l) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
13. (m) Chen, D. Y.-K.; Youn, S. W. Chem.. Eur. J. 2012, 18, 9452.
14. (n) Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.. Eur. J. 2010, 16, 2654.
15. (o) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890.
16. (p) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
17. (q) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
18. (r) Wencel-Delord, J.; Dräge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740.
19. For selected reviews: (a) Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3464.
20. (b) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068.
21. (c) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
22. (d) McGlacken, G. P.; Bateman, L. M. Chem. Soc. Rev. 2009, 38, 2447.
23. (e) Ashenhurst, J. A. Chem. Soc. Rev. 2010, 39, 540.
24. (f) Li, C.-J. Acc. Chem. Res. 2009, 42, 335.
25. (a) The Alkaloids: Chemistry and Biology; Knälker, H.-J., Ed.; Elsevier: San Diego, CA, 2011; Vol. 70.
26. (b) Ciric-Marjanovic, G. Synth. Met. 2013, 177, 1.
27. For some recent selected examples on tandem C (sp2)-H/N-H activation, see: (a) Antonchick, A. P.; Samanta, R.; Kulikov, K.; Lategahn, J. Angew. Chem., Int. Ed. 2011, 50, 8605.
28. (b) Kim, H. J.; Kim, J.; Cho, S. H.; Chang, S. J. Am. Chem. Soc. 2011, 133, 16382.
29. (c) Kantak, A. A.; Potavathri, S.; Barham, R. A.; Romano, K. M.; De Boef, B. J. Am. Chem. Soc. 2011, 133, 19960.
30. (d) Shrestha, R.; Mukherjee, P.; Tan, Y.; Litman, Z. C.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 8480.
31. (e) Alla, S. K.; Kumar, R. K.; Sadhu, P.; Punniyamurthy, T. Org. Lett. 2013, 15, 1334.
32. (f) Tran, L. D.; Roane, J.; Daugulis, O. Angew. Chem., Int. Ed. 2013, 52, 6043.
33. (g) Samanta, R.; Bauer, J. O.; Strohmann, C.; Antonchick, A. P. Org. Lett. 2012, 14, 5518.
34. (h) Huang, J.; He, Y.; Wang, Y.; Zhu, Q. Chem.. Eur. J. 2012, 18, 13964.
35. (i) Oda, Y.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2012, 14, 664.
36. (j) Cho, S. H.; Yoon, J.; Chang, S. J. Am. Chem. Soc. 2011, 133, 5996.
37. (k) Lamani, M.; Prabhu, K. R. J. Org. Chem. 2011, 76, 7938.
38. (l) Kim, J. Y.; Cho, S. H.; Joseph, J.; Chang, S. Angew. Chem., Int. Ed. 2010, 49, 9899.
39. (m) Wang, J.; Hou, J.-T.; Wen, J.; Zhang, J.; Yu, X.-Q. Chem. Commun. 2011, 47, 3652.
40. (n) John, A.; Nicholas, K. M. J. Org. Chem. 2011, 76, 4158.
41. (o) Xiao, B.; Gong, T.-J.; Xu, J.; Liu, Z.-J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 1466.
42. (p) Sun, K.; Li, Y.; Xiong, T.; Zhang, J.; Zhan, Q. J. Am. Chem. Soc. 2011, 133, 1694.
43. (q) Yoo, E. J.; Ma, S.; Mei, T.-S.; Chan, K. S. L.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 7652.
44. For some selected examples on tandem C (sp3)-H/N-H activation, see: (a) Evans, R. W.; Zbieg, J. R.; Zhu, S.; Li, W.; MacMillan, D. W. C. J. Am. Chem. Soc. 2013, 135, 16074.
45. (b) Lamani, M.; Prabhu, K. R. Chem.. Eur. J. 2012, 18, 14638.
46. (c) Tian, J.-S.; Ng, K. W. J.; Wong, J.-R.; Loh, T.-P. Angew. Chem., Int. Ed. 2012, 51, 9105.
47. (d) Mao, L.; Li, Y.; Xiong, T.; Sun, K.; Zhang, Q. J. Org. Chem. 2013, 78, 733.
48. (e) Souto, J. A.; Zian, D.; Muniz, K. J. Am. Chem. Soc. 2012, 134, 7242.
49. (f) Lv, Y.; Li, Y.; Xiong, T.; Lu, Y.; Liu, Q.; Zhang, Q. Chem. Commun. 2014, 50, 2367.
50. (a) Xu, J.-H.; Jiang, Q.; Guo, C.-C. J. Org. Chem. 2013, 78, 11881.
51. (b) Jiang, Q.; Zhao, A.; Xu, B.; Jia, J.; Liu, X.; Guo, C. J. Org. Chem. 2014, 79, 2709.
52. (c) Jiang, Q.; Sheng, W.; Guo, C. Green Chem. 2013, 15, 2175.
53. (d) Wang, J.-Y.; Jiang, Q.; Guo, C.-C. Synth. Commun. 2014, DOI: 10.1080/00397911.2014.928938.
54. (a) Meltzer, P. C.; Butler, D.; Deschamps, J. R.; Madras, B. K. J. Med. Chem. 2006, 49, 1420.
55. (b) Carrol, F. I.; Blough, B. E.; Abraham, P.; Mills, A. C.; Holleman, J. A.; Wolchenhauer, S. A.; Decker, A. M.; Landavazo, A. K.; McElroy, T.; Navarro, H. A.; Gatch, M. B.; Forster, M. J. J. Med. Chem. 2009, 52, 6768.
56. (c) Bouteiller, C.; Becerril-Ortega, J.; Marchand, P.; Nicole, O.; Barre, L.; Buisson, A.; Perrio, C. Org. Biomol. Chem. 2010, 8, 1111.
57. (d) Meyers, M. C.; Wang, J.-L.; Iera, J. A.; Bang, J.-K.; Hara, T.; Saito, S.; Zambetti, G. P.; Appella, D. H. J. Am. Chem. Soc. 2005, 127, 6152.
58. (a) Paleo, M. R.; Calaza, M. I.; Sardina, F. J. J. Org. Chem. 1997, 62, 6862.
59. (b) Hill, R. K.; Nugara, P. N.; Holt, E. M.; Holland, K. P. J. Org. Chem. 1992, 57, 1045.
60. (c) Belot, S.; Sulzer-Moss, S.; Kehrli, S.; Alexakis, A. Chem. Commun. 2008, 4694.
61. (a) Negishi, E. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; Vol. I, pp 213-1119.
62. (b) Metal-Catalyzed Cross-Coupling Reactions; De Meijere, A.; Diederich, F., Eds.; Wiley-VCH: New York, 2004; and references therein.
63. (c) Yu, D.-G.; Li, B.-J.; Shi, Z.-J. Acc. Chem. Res. 2010, 43, 1486.
64. Silverstone, T. Drugs 1992, 43, 820.
65. For selected reviews and examples on I2-catalyzed reactions, see: (a) Zhang, J.; Zhu, D.; Yu, C.; Wan, C.; Wang, Z. Org. Lett. 2010, 12, 2841.
66. (b) Do, H. Q.; Daugulis, O. J. Am. Chem. Soc. 2011, 133, 13577.
67. (c) Uyanik, M.; Ishihara, K. Chem Cat Chem 2012, 4, 177.
68. (d) Wei, W.; Shao, Y.; Hu, H. Y.; Zhang, F.; Zhang, C.; Xu, Y.; Wan, X. B. J. Org. Chem. 2012, 77, 7157.
69. (e) Parvatkar, P. T.; Parameswaran, P. S.; Tilve, S. G. Chem.. Eur. J. 2012, 18, 5460.
70. (f) Zhu, Y. P.; Liu, M. C.; Jia, F. C.; Yuan, J. J.; Gao, Q. H.; Lian, M.; Wu, A. X. Org. Lett. 2012, 14, 3392.
71. (g) Gao, M.; Yang, Y.; Wu, Y. D.; Deng, C.; Cao, L. P.; Meng, X. G.; Wu, A. X. Org. Lett. 2010, 12, 1856.
72. (h) Yin, G. D.; Zhou, B. H.; Meng, X. G.; Wu, A. X.; Pan, Y. J. Org. Lett. 2006, 8, 2245.