Orthogonal reactivity of acyl azides in C-H activation: Dichotomy between C-C and C-N amidations based on catalyst systems

Organic Letters

Volumn 16, Issue 7, 2014, Pages 2022-2025

  Shin, Kwangmin ^a,b   Ryu, Jaeyune ^a,b   Chang, Sukbok ^a,b  

^a Institute for Basic Science   (South Korea)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84898716383     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500602b     Document Type: Article

References (52)

1. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
2. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
3. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
4. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
5. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788
6. Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726
7. Jun, C.-H.; Moon, C. W.; Lee, D.-Y. Chem. Eur. J. 2002, 8, 2422
8. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
9. Satoh, T.; Miura, M. Chem. Eur. J. 2010, 16, 11212
10. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651
11. Zhou, C.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 2302
12. Tsai, A. S.; Tauchert, M. E.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2011, 133, 1248
13. Li, Y.; Li, B.-J.; Wang, W.-H.; Huang, W.-P.; Zhang, X.-S.; Chen, K.; Shi, Z.-J. Angew. Chem., Int. Ed. 2011, 50, 2115
14. Lian, Y.; Huber, T.; Hesp, K. D.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2013, 52, 629
15. Yoshino, T.; Ikemoto, H.; Matsunaga, S.; Kanai, M. Angew. Chem., Int. Ed. 2013, 52, 2207
16. Kuninobu, Y.; Tokunaga, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128, 202
17. Kuninobu, Y.; Tokunaga, Y.; Takai, K. Chem. Lett. 2007, 36, 872
18. Hesp, K. D.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2011, 133, 11430
19. Muralirajan, K.; Parthasarathy, K.; Cheng, C.-H. Org. Lett. 2012, 14, 4262
20. Zhou, B.; Hou, W.; Yang, Y.; Li, Y. Chem. Eur. J. 2013, 19, 4701
21. Curtius, T. Ber. Dtsch. Chem. Ges. 1890, 23, 3023
22. Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188
23. Lebel, H.; Leogane, O.; Huard, K.; Lectard, S. Pure Appl. Chem. 2006, 78, 363
24. Wang, Y.-F.; Chiba, S. J. Am. Chem. Soc. 2009, 131, 12570
25. Nguyen, Q.; Sun, K.; Driver, T. G. J. Am. Chem. Soc. 2012, 134, 7262
26. Nishioka, Y.; Uchida, T.; Katsuki, T. Angew. Chem., Int. Ed. 2013, 52, 1739
27. Hennessy, E. T.; Betley, T. A. Science 2013, 340, 591
28. Yu, D.-G.; Suri, M.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 8802
29. Lian, Y.; Hummel, J. R.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2013, 135, 12548
30. Kim, J. Y.; Park, S. H.; Ryu, J.; Cho, S. H.; Kim, S. H.; Chang, S. J. Am. Chem. Soc. 2012, 134, 9110
31. Ryu, J.; Shin, K.; Park, S. H.; Kim, J. Y.; Chang, S. Angew. Chem., Int. Ed. 2012, 51, 9904
32. Shin, K.; Baek, Y.; Chang, S. Angew. Chem., Int. Ed. 2013, 52, 8031
33. Park, S. H.; Park, Y.; Chang, S. Org. Synth. 2014, 91, 52
34. Kim, H. J.; Ajitha, M. J.; Lee, Y.; Ryu, J.; Kim, J.; Lee, Y.; Jung, Y.; Chang, S. J. Am. Chem. Soc. 2014, 136, 1132
35. Park, S. H.; Kwak, J.; Shin, K.; Ryu, J.; Park, Y.; Chang, S. J. Am. Chem. Soc. 2014, 136, 2492
36. Kim, J.; Kim, J.; Chang, S. Chem. Eur. J. 2013, 19, 7328
37. Ryu, J.; Kwak, J.; Shin, K.; Lee, D.; Chang, S. J. Am. Chem. Soc. 2013, 135, 12861
38. Lee, D.; Kim, Y.; Chang, S. J. Org. Chem. 2013, 78, 11102
39. Kim, J.; Chang, S. Angew. Chem., Int. Ed. 2014, 53, 2203
40. Umeda, N.; Tsurugi, H.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2008, 47, 4019
41. Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908
42. Rakshit, S.; Grohmann, C.; Besset, T.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2350
43. Li, H.; Li, Y.; Zhang, X.-S.; Chen, K.; Wang, X.; Shi, Z.-J. J. Am. Chem. Soc. 2011, 133, 15244
44. Chan, W.-W.; Lo, S.-F.; Zhou, Z.; Yu, W.-Y. J. Am. Chem. Soc. 2012, 134, 13565
45. Hyster, T. K.; Knörr, L.; Ward, T. R.; Rovis, T. Science 2012, 338, 500
46. White, C.; Thompson, S. J.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1977, 1654
47. Ackermann, L. Chem. Rev. 2011, 111, 1315
48. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879
49. Ackermann, L. Acc. Chem. Res. 2014, 47, 281
50. Ackermann, L.; Vicente, R.; Althammer, A. Org. Lett. 2008, 10, 2299
51. Ackermann, L.; Vicente, R.; Potukuchi, H. K.; Pirovano, V. Org. Lett. 2010, 12, 5032
52. Flegeau, E. F.; Bruneau, C.; Dixneuf, P. H.; Jutand, A. J. Am. Chem. Soc. 2011, 133, 10161