Rhodium-catalyzed alkylation of C-H bonds in aromatic amides with α,β-unsaturated esters

Organic Letters

Volumn 16, Issue 19, 2014, Pages 5148-5151

  Shibata, Kaname ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84907701100     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502500c     Document Type: Article

References (56)

1. Thirunavukkarasu, V. S.; Kozhushkov, S. I.; Ackermann, L. Chem. Commun. 2014, 50, 29
2. Girard, S. A.; Knauber, T.; Li, C.-J. Angew. Chem., Int. Ed. 2014, 53, 74
3. Ackermann, L. Acc. Chem. Res. 2014, 47, 281
4. Miura, M.; Satoh, T.; Hirano, K. Bull. Chem. Soc. Jpn. 2014, 87, 751
5. Gao, K.; Yoshikai, N. Acc. Chem. Res. 2014, 47, 1208
6. Kapdi, A. R. Dalton Trans. 2014, 43, 3021
7. For a review on C-H bond alkylation with alkyl halides, see: Ackermann, L. Chem. Commun. 2010, 46, 4866
8. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529
9. Kakuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62
10. Simon, M.-O.; Ung, G.; Darses, S. Adv. Synth. Catal. 2011, 353, 1045
11. Qi, J.; Huang, L.; Wang, Z.; Jiang, H. Org. Biomol. Chem. 2013, 11, 8009
12. Schinkel, M.; Marek, I.; Ackermann, L. Angew. Chem., Int. Ed. 2013, 52, 3977
13. Lim, S.-G.; Ahn, J.-A.; Jun, C.-H. Org. Lett. 2004, 6, 4687
14. Park, Y. J.; Jun, C.-H. Bull. Korean Chem. Soc. 2005, 26, 871
15. Kuninobu, Y.; Nishina, Y.; Okaguchi, K.; Shouho, M.; Takai, K. Bull. Chem. Soc. Jpn. 2008, 81, 1393
16. Kuninobu, T.; Kikuchi, K.; Tokunaga, Y.; Nishina, Y.; Takai, K. Tetrahedron 2008, 64, 5974
17. Yang, L.; Correia, C. A.; Li, C.-J. Org. Biomol. Chem. 2011, 9, 7176
18. Yang, L.; Qian, B.; Huang, H. Chem. - Eur. J. 2012, 18, 9511
19. Pan, S.; Ryu, N.; Shibata, T. Adv. Synth. Catal. 2014, 356, 929
20. Shibata, T.; Shizuno, T. Angew. Chem., Int. Ed. 2014, 53, 5410
21. Kommagalla, Y.; Srinivas, K.; Ramana, C. V. Chem. - Eur. J. 2014, 20, 7884
22. Rouquet, G.; Chatani, N. Chem. Sci. 2013, 4, 2201
23. Kozhushkov, S. I.; Ackermann, L. Chem. Sci. 2013, 4, 886
24. Zhou, L.; Lu, W. Chem. - Eur. J. 2014, 20, 634
25. Melnick, M.; Reich, S. H.; Lewis, K. K.; Mitchell, L. J., Jr.; Nguyen, D.; Trippe, A. J.; Dawson, H.; Davies, J. F., II; Appelt, K.; Wu, B.-W.; Musick, L.; Gehlhaar, D. K.; Webber, S.; Shetty, B.; Kosa, M.; Kahil, D.; Andrada, D. J. Med. Chem. 1996, 39, 2795
26. Asada, M.; Obitsu, T.; Nagase, T.; Tanaka, M.; Yamaura, Y.; Takizawa, H.; Yoshikawa, K.; Sato, K.; Narita, M.; Ohuchida, S.; Nakai, H.; Toda, M. Bioorg. Med. Chem. 2010, 18, 80
27. Asada, M.; Iwahashi, M.; Obitsu, T.; Kinoshita, A.; Nakai, Y.; Onoda, T.; Nagase, T.; Tanaka, M.; Yamaura, Y.; Takizawa, H.; Yoshikawa, K.; Sato, K.; Narita, M.; Ohuchida, S.; Nakai, H.; Toda, M. Bioorg. Med. Chem. 2010, 18, 1641
28. Asada, M.; Obitsu, T.; Kinoshita, A.; Nagase, T.; Yoshida, T.; Yamaura, Y.; Takizawa, H.; Yoshikawa, K.; Sato, K.; Narita, M.; Nakai, H.; Toda, M.; Tobe, Y. Bioorg. Med. Chem. 2010, 18, 321
29. U.S. Pat. Appl. Publ. 20120270915, Oct 25, 2012).
30. Oxidative alkenylation of C-H bonds in amides followed by hydrogenation with Pd/C was carried out to construct 3-(2-carbamoylphenyl)propanoate. Yadav, M. R.; Rit, R. K.; Shankar, M.; Sahoo, A. K. J. Org. Chem. 2014, 79, 6123
31. Corbet, M.; De Campo, F. Angew. Chem., Int. Ed. 2013, 52, 9896
32. Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726
33. Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3680
34. Wang, F.; Song, G.; Li, X. Org. Lett. 2010, 12, 5430
35. Hashimoto, Y.; Ueyama, T.; Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M. Chem. Lett. 2011, 40, 1165
36. Zhu, C.; Falck, J. R. Org. Lett. 2011, 13, 1214
37. Wrigglesworth, J. W.; Cox, B.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. Org. Lett. 2011, 13, 5326
38. Ackermann, L.; Wang, L.; Wolfram, R.; Lygin, A. V. Org. Lett. 2012, 14, 728
39. Zhu, C.; Falck, J. R. Tetrahedron 2012, 68, 9192
40. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814
41. Pan, F.; Lei, Z.-Q.; Wang, H.; Li, H.; Sun, J.; Shi, Z.-J. Angew. Chem., Int. Ed. 2013, 52, 2063
42. Zhou, W.; Yang, Y.; Wang, Z.; Deng, G.-J. Org. Biomol. Chem. 2014, 12, 251
43. Aïssa, C.; Ho, K. Y. T.; Tetlow, D. J.; Pin-Nó, M. Angew. Chem., Int. Ed. 2014, 53, 4209
44. Keske, E. C.; Moore, B. D.; Zenkina, O. V.; Wang, R.; Schatte, G.; Crudden, C. M. Chem. Commun. 2014, 50, 9883
45. Inoue, S.; Shiota, H.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 6898
46. Hasegawa, N.; Charra, V.; Inoue, S.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 8070
47. Shiota, H.; Ano, Y.; Aihara, Y.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 14952
48. Shibata, K.; Hasegawa, N.; Fukumoto, Y.; Chatani, N. ChemCatChem. 2012, 4, 1733
49. Hasegawa, N.; Shibata, K.; Charra, V.; Inoue, S.; Fukumoto, Y.; Chatani, N. Tetrahedron 2013, 69, 4466
50. Ano, Y.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 12984
51. Ano, Y.; Tobisu, M.; Chatani, N. Org. Lett. 2012, 14, 354
52. Aihara, Y.; Chatani, N. Chem. Sci. 2013, 4, 664
53. Aihara, Y.; Chatani, N. J. Am. Chem. Soc. 2013, 135, 5308
54. Aihara, Y.; Chatani, N. J. Am. Chem. Soc. 2014, 136, 898
55. Yokota, A.; Aihara, Y.; Chatani, N. J. Org. Chem. 2014, 10.1021/jo501697n
56. Iyanaga, M.; Aihara, Y.; Chatani, N. J. Org. Chem. 2014, 10.1021/jo501691f