Silver-catalyzed carboazidation of arylacrylamides

Organic Letters

Volumn 15, Issue 16, 2013, Pages 4158-4161

  Wei, Xiao Hong ^a   Li, Ya Min ^a   Zhou, An Xi ^a   Yang, Ting Ting ^a   Yang, Shang Dong ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84882793502     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol402138y     Document Type: Article

References (58)

1. Sibbald, P. A. Palladium-Catalyzed Oxidative Difunctionalization of Alkenes: New Reactivity and New Mechanisms; ProQuest: UMI, 2011.
2. Jacques, B.; Muiñz, K. In Catalyzed Carbon-Heteroatom Bond Formation; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, 2011; p 119
3. McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981
4. Muiñz, K. Angew. Chem., Int. Ed. 2009, 48, 9412
5. Chemler, S. R. Org. Biomol. Chem. 2009, 7, 3009
6. Jensen, K. H.; Sigman, M. S. Org. Biomol. Chem. 2008, 6, 4083
7. Kotov, V.; Scarborough, C. C.; Stahl, S. S. Inorg. Chem. 2007, 46, 1910
8. Li, G.; Kotti, S. R. S. S.; Timmons, C. Eur. J. Org. Chem. 2007, 17, 2745
9. Jaegli, S.; Dufour, J.; Wei, H.; Piou, T.; Duan, X.; Vors, J.; Neuville, L.; Zhu, J. Org. Lett. 2010, 12, 4498
10. Jaegli, S.; Erb, W.; Retailleau, P.; Vors, J.; Neuville, L.; Zhu, J. Chem.-Eur. J. 2010, 16, 5863
11. Wu, T.; Mu, X.; Liu, G. Angew. Chem., Int. Ed. 2011, 50, 12578
12. Mu, X.; Wu, T.; Wang, H.; Guo, Y.; Liu, G. J. Am. Chem. Soc. 2012, 134, 878
13. Broggini, G.; Barbera, V.; Beccalli, E. M.; Borsini, E.; Galli, S.; Lanza, G.; Zecchi, G. Adv. Synth. Catal. 2012, 354, 159
14. An, G.; Zhou, W.; Zhang, G.; Sun, H.; Han, J.; Pan, Y. Org. Lett. 2010, 12, 4482
15. Pinto, A.; Jia, Y.; Neuville, L.; Zhu, J. Chem.-Eur. J. 2007, 13, 961
16. Han, X.; Lu, X. Org. Lett. 2009, 11, 2381
17. Wei, W.-T.; Zhou, M.-B.; Fan, J.-H.; Liu, W.; Song, R.-J.; Liu, Y.; Hu, M.; Xie, P.; Li, J.-H. Angew. Chem., Int. Ed. 2013, 52, 3638
18. Xie, J.; Xu, P.; Li, H.; Xue, Q.; Jin, H.; Cheng, Y.; Zhu, C. Chem. Commun. 2013, 49, 5672
19. Hu, J.; Zhao, N.; Yang, B.; Wang, G.; Guo, L.-N.; Liang, Y.-M.; Yang, S.-D. Chem.-Eur. J. 2011, 17, 5516
20. Sun, M.; Zhang, H.-Y.; Han, Q.; Yang, K.; Yang, S.-D. Chem.-Eur. J. 2011, 17, 9566
21. Zhang, H.-Y.; Zhou, A.-X; Li, Y.-M.; Yang, S.-D. Org. Biomol. Chem. 2012, 10, 9627
22. Li, Y.-M.; Sun, M.; Wang, H.-L.; Tian, Q.-P.; Yang, S.-D. Angew. Chem., Int. Ed. 2013, 52, 3972
23. Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188
24. Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297
25. Smith, P. A. S. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Ed.; Academic Press: Orlando, 1984.
26. Bräse, S.; Banert, K. Organic Azides: Syntheses and Applications; Wiley: Chichester, 2010.
27. Prabhu, K. R.; Pillarsetty, N.; Gali, H.; Katti, K. V. J. Am. Chem. Soc. 2000, 122, 1554
28. Hsiao, Y.; Hegedus, L. S. J. Org. Chem. 1997, 62, 3586
29. Roychowdhury, A.; Illangkoon, H.; Hendrickson, C. L.; Benner, S. A. Org. Lett. 2004, 6, 489
30. Saito, Y.; Matsumoto, K.; Bag, S. S.; Ogasawara, S.; Fujimoto, K.; Hanawa, K.; Saito, I. Tetrahedron 2008, 64, 3578
31. Zhou, L.; Gao, C.; Zhu, D. D.; Xu, W. J.; Frank Chen, F. Q.; Amit, P.; Echegoyen, L.; Kong, E. S.W. Chem.-Eur. J. 2009, 15, 1389
32. Jimeno, C.; Renaud, P. Radical Chemistry with Azides, in Organic Azides: Syntheses and Applications; Bräse, S.; Banert, K., Eds.; Wiley: Chichester, 2010.
33. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004
34. Binder, W. H.; Kluger, C. Curr. Org. Chem. 2006, 10, 1791
35. Debets, M. F.; van Berkel, S. S.; Dommerholt, J.; Dirks, A. J.; Rutjes, F. P. J. T.; van Delft, F. L. Acc. Chem. Res. 2011, 44, 805
36. Amblard, F.; Cho, J. H.; Schinazi, R. F. Chem. Rev. 2009, 109, 4207
37. Köhn, M.; Breinbauer, R. Angew. Chem., Int. Ed. 2004, 43, 3106
38. Workentin, M. S.; Wagner, B. D.; Lusztyk, J.; Wayner, D. D. M. J. Am. Chem. Soc. 1995, 117, 119
39. Stell, L. In Radical in Organic Synthesis; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, p 407.
40. Lapointe, G.; Kapat, A.; Weidner, K.; Renaud, P. Pure Appl. Chem. 2012, 84, 1633
41. Zard, S. Z. Chem. Soc. Rev. 2008, 37, 1603
42. Minozzi, M.; Nanni, D.; Spagnolo, P. Chem.-Eur. J. 2009, 15, 7830
43. Kapat, A.; König, A. K; Montermini, F.; Renaud, P. J. Am. Chem. Soc. 2011, 133, 13890
44. Lapointe, G.; Schenk, K.; Renaud, P. Chem.-Eur. J. 2011, 17, 3207
45. Weidner, K.; Giroult, A.; Panchaud, P.; Renaud, P. J. Am. Chem. Soc. 2010, 132, 17511
46. Chouthaiwale, P. V.; Karabal, P. U.; Suryavanshi, G.; Sudalai, A. Synthesis 2010, 3879
47. Waser, J.; Gaspar, B.; Nambu, H.; Carreira, E. M. J. Am. Chem. Soc. 2006, 128, 11693
48. Chung, R.; Yu, E.; Incarvito, C. D.; Austin, D. J. Org. Lett. 2004, 6, 3881
49. Tiecco, M.; Testaferri, L.; Santi, C.; Tomassini, C.; Marini, F.; Bagnoli, L.; Temperini, A. Angew. Chem., Int. Ed. 2003, 42, 3131
50. Magnus, P.; Lacour, J.; Evans, P. A.; Roe, M. B.; Hulme, C. J. Am. Chem. Soc. 1996, 118, 3406
51. Trahanovsky, W. S.; Robbins, M. D. J. Am. Chem. Soc. 1971, 93, 5256
52. Hassner, A.; Levy, L. A. J. Am. Chem. Soc. 1965, 87, 4203
53. Lizos, D. E.; Murphy, J. A. Org. Biomol. Chem. 2003, 1, 117
54. Bindra, J. S. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1973; p 84.
55. Cui, C. B.; Kakeya, H.; Osada, H. Tetrahedron 1996, 52, 12651
56. Renaud, P.; Ollivier, C.; Panchaud, P. Angew. Chem., Int. Ed. 2002, 41, 3460
57. Montanari, F.; Quici, S.; Henry-Riyad, H.; Tidwell, T. T. 2,2,6,6-Tetramethylpiperidin-1-oxyl. Encyclopedia of Reagents for Organic Synthesis; Wiley: New York, 2005.
58. Frazier, C. P.; Engelking, J. R.; Alaniz, J. R. J. Am. Chem. Soc. 2011, 133, 10430