Iridium-catalyzed direct C-H amidation with weakly coordinating carbonyl directing groups under mild conditions

Angewandte Chemie - International Edition

Volumn 53, Issue 8, 2014, Pages 2203-2207

  Kim, Jinwoo ^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

azides; C H amidation; esters; iridium; weakly coordinating groups

Indexed keywords

AMIDATION; AZIDES; DIRECTING GROUPS; KETONE GROUP; LITHIUM CARBONATES; REACTION EFFICIENCY; WEAKLY COORDINATING GROUPS;

CATALYSIS; ESTERIFICATION; ESTERS; KETONES;

IRIDIUM;

EID: 84893857090     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201310544     Document Type: Article

References (62)

1. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, Nature 1993, 366, 529.
2. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
3. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
4. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651
5. I. P. Beletskaya, A. V. Cheprakov, Organometallics 2012, 31, 7753
6. P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 2012, 112, 5879
7. G. Rouquet, N. Chatani, Angew. Chem. 2013, 125, 11942
8. Angew. Chem. Int. Ed. 2013, 52, 11726.
9. K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788.
10. B. M. Trost, K. Imi, I. W. Davies, J. Am. Chem. Soc. 1995, 117, 5371
11. M. Sonoda, F. Kakiuchi, A. Kamatani, N. Chatani, S. Murai, Chem. Lett. 1996, 25, 109
12. S. Kawamorita, H. Ohmiya, K. Hara, A. Fukuoka, M. Sawamura, J. Am. Chem. Soc. 2009, 131, 5058
13. N. M. Neisius, B. Plietker, Angew. Chem. 2009, 121, 5863
14. Angew. Chem. Int. Ed. 2009, 48, 5752
15. B. Xiao, Y. Fu, J. Xu, T.-J. Gong, J.-J. Dai, J. Yi, L. Liu, J. Am. Chem. Soc. 2010, 132, 468
16. K. Kitazawa, M. Kotani, T. Kochi, M. Langeloth, F. Kakiuchi, J. Organomet. Chem. 2010, 695, 1163
17. S. H. Park, J. Y. Kim, S. Chang, Org. Lett. 2011, 13, 2372
18. T. Besset, N. Kuhl, F. W. Patureau, F. Glorius, Chem. Eur. J. 2011, 17, 7167
19. Y. Yang, Y. Lin, Y. Rao, Org. Lett. 2012, 14, 2874
20. K. Graczyk, W. Ma, L. Ackermann, Org. Lett. 2012, 14, 4110
21. G. Shan, X. Yang, L. Ma, Y. Rao, Angew. Chem. 2012, 124, 13247
22. Angew. Chem. Int. Ed. 2012, 51, 13070.
23. P. G. M. Wuts, T. W. Greene, Greene's Protective Groups in Organic Synthesis, Wiley, Hoboken, 2006.
24. R. C. Larock, Comprehensive Organic Transformations, Wiley, New York, 1999.
25. L. Ackermann, Chem. Rev. 2011, 111, 1315
26. L. Ackermann, Acc. Chem. Res. 2013, DOI:.
27. Y. Jiang, J. Hess, T. Fox, H. Berke, J. Am. Chem. Soc. 2010, 132, 18233
28. E. FerrerFlegeau, C. Bruneau, P. H. Dixneuf, A. Jutand, J. Am. Chem. Soc. 2011, 133, 10161
29. T. Shiba, T. Kurahashi, S. Matsubara, J. Am. Chem. Soc. 2013, 135, 13636.
30. J. Y. Kim, S. H. Park, J. Ryu, S. H. Cho, S. H. Kim, S. Chang, J. Am. Chem. Soc. 2012, 134, 9110
31. J. Ryu, K. Shin, S. H. Park, J. Y. Kim, S. Chang, Angew. Chem. 2012, 124, 10042
32. Angew. Chem. Int. Ed. 2012, 51, 9904
33. J. Kim, J. Kim, S. Chang, Chem. Eur. J. 2013, 19, 7328
34. K. Shin, Y. Baek, S. Chang, Angew. Chem. 2013, 125, 8189
35. Angew. Chem. Int. Ed. 2013, 52, 8031
36. J. Ryu, J. Kwak, K. Shin, D. Lee, S. Chang, J. Am. Chem. Soc. 2013, 135, 12861
37. D. Lee, Y. Kim, S. Chang, J. Org. Chem. 2013, 78, 11102
38. S. H. Park, Y. Park, S. Chang, Org. Synth. 2014, 91, 52.
39. M. Meldal, C. W. Tornøe, Chem. Rev. 2008, 108, 2952
40. G. Dequirez, V. Pons, P. Dauban, Angew. Chem. 2012, 124, 7498
41. Angew. Chem. Int. Ed. 2012, 51, 7384
42. S. Chiba, Synlett 2012, 21
43. K. Sun, R. Sachwani, K. J. Richert, T. G. Driver, Org. Lett. 2009, 11, 3598
44. H. Zhao, M. Wang, W. Su, M. Hong, Adv. Synth. Catal. 2010, 352, 1301
45. H. Zhao, Y. Shang, W. Su, Org. Lett. 2013, 15, 5106.
46. A. H. Janowicz, R. G. Bergman, J. Am. Chem. Soc. 1982, 104, 352
47. R. G. Bergman, Science 1984, 223, 902
48. J. A. Labinger, J. E. Bercaw, Nature 2002, 417, 507
49. J. Liu, X. Wu, J. A. Iggo, J. Xiao, Coord. Chem. Rev. 2008, 252, 782
50. K. L. Engelman, Y. Feng, E. A. Ison, Organometallics 2011, 30, 4572.
51. Fagnou and co-workers reasoned that a carbonate base makes a C-H cleavage step irreversible by segregating an abstracted proton as a less-soluble bicarbonate salt; see:, S. Rousseaux, S. I. Gorelsky, B. K. W. Chung, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 10692.
52. T. Katsuki, Chem. Lett. 2005, 34, 1304
53. S. Cenini, E. Gallo, A. Caselli, F. Ragaini, S. Fantauzzi, C. Piangiolino, Coord. Chem. Rev. 2006, 250, 1234
54. H.-Y. Thu, W.-Y. Yu, C.-M. Che, J. Am. Chem. Soc. 2006, 128, 9048
55. W. G. Shou, J. Li, T. Guo, Z. Lin, G. Jia, Organometallics 2009, 28, 6847
56. Y. Liu, X. Guan, E. L.-M. Wong, P. Liu, J.-S. Huang, C.-M. Che, J. Am. Chem. Soc. 2013, 135, 7194.
57. C. Z. Ding, etal., J. Med. Chem. 1999, 42, 5241 (for the full author list, see the Supporting Information)
58. J. I. Levin, F. C. Nelson, E. DelosSantos, M. T. Du, G. MacEwan, J. M. Chen, S. Ayral-Kaloustian, J. Xu, G. Jin, T. Cummons, D. Barone, Bioorg. Med. Chem. Lett. 2004, 14, 4147
59. E. A. Stigter, Z. Guo, R. S. Bon, Y.-W. Wu, A. Choidas, A. Wolf, S. Menninger, H. Waldmann, W. Blankenfeldt, R. S. Goody, J. Med. Chem. 2012, 55, 8330.
60. B. Xiao, T.-J. Gong, J. Xu, Z.-J. Liu, L. Liu, J. Am. Chem. Soc. 2011, 133, 1466.
61. D. L. Davies, O. Al-Duaij, J. Fawcett, M. Giardiello, S. T. Hilton, D. R. Russell, Dalton Trans. 2003, 4132
62. Y. Boutadla, O. Al-Duaij, D. L. Davies, G. A. Griffith, K. Singh, Organometallics 2009, 28, 433.