Lewis basic selenium catalyzed chloroamidation of olefins using nitriles as the nucleophiles

Organic Letters

Volumn 15, Issue 6, 2013, Pages 1310-1313

  Tay, Daniel Weiliang ^a,b   Tsoi, Ivan Tan ^a,b   Er, Jun Cheng ^a   Leung, Gulice Yiu Chung ^b   Yeung, Ying Yeung ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84875178340     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400249x     Document Type: Article

References (52)

1. Kemp, J. E. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 471-513 and references cited therein.
2. Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1991, 113, 5863-5864
3. Driguez, H.; Vermes, J. P.; Lessard, J. Can. J. Chem. 1978, 56, 119-130
4. Doniher, F. A.; Butler, P. E. J. Org. Chem. 1968, 33, 4336-4340
5. Orlek, B. S.; Stemp, G. Tetrahedron Lett. 1991, 32, 4045-4048
6. Barton, D. H. R.; Britten-Kelly, M. R.; Ferreira, D. J. Chem. Soc., Perkin Trans. 1 1978, 1090-1100
7. Lessard, J.; Driguez, H.; Vermes, J.-P. Tetrahedron Lett. 1970, 11, 4887-4891
8. Qui, J.; Silverman, R. B. J. Med. Chem. 2000, 43, 706-720
9. Karur, S.; Kotti, S. R. S. S.; Xu, X.; Cannon, J. F.; Headley, A. D.; Li, G. J. Am. Chem. Soc. 2003, 125, 13340-13341
10. Li, G.; Wei, H.-X.; Kim, S. H. Org. Lett. 2000, 2, 2249-2252
11. Wei, H.-X.; Kim, S. H.; Li, G. Tetrahedron 2001, 57, 3869-3973
12. Chen, D.; Timmons, C.; Chao, S.; Li, G. Eur. J. Org. Chem. 2004, 3097-3101
13. Kotti, S. R. S. S.; Xu, X.; Wang, Y.; Headley, A. D.; Li, G. Tetrahedron Lett. 2004, 45, 7209-7212
14. Thakur, V. V.; Talluri, S. K.; Sudalai, A. Org. Lett. 2003, 5, 861-864
15. Volonterio, A.; Bravo, P.; Panzeri, W.; Pesenti, C.; Zanda, M. Eur. J. Org. Chem. 2002, 19, 3336-3340
16. Bach, T.; Schlummer, B.; Harms, K. Chem. Commun. 2000, 287-288
17. Kirschning, A.; Hashem, M. D.; Monenschein, H.; Rose, L.; Schonng, K. U. J. Org. Chem. 1999, 64, 6522-6526
18. Bellucci, G.; Bianchini, R.; Chiappe, C. J. Org. Chem. 1991, 56, 3067-3073
19. Jung, S. H.; Kohn, H. J. Am. Chem. Soc. 1985, 107, 2931-2943
20. Wang, Z. G.; Warren, J. D.; Dudkin, V. Y.; Zhang, X.; Iserloh, U.; Visser, M.; Eckhardt, M.; Seeberger, P. H.; Danishefsky, S. J. Tetrahedron 2006, 62, 4954-4978
21. Li, G.; Kotti, S. R. S. S.; Timmons, C. Eur. J. Org. Chem. 2007, 2745-2758
22. Feng, X. Angew. Chem., Int. Ed. 2010, 49, 6160-6164
23. Cai, Y.; Liu, X.; Jiang, J.; Chen, W.; Lin, L.; Feng, X. J. Am. Chem. Soc. 2011, 133, 5636-5639
24. Cai, Y.; Liu, X.; Li, J.; Chen, W.; Wang, W.; Lin, L.; Feng, X. Chem.-Eur. J. 2011, 17, 14916-14921
25. Yeung, Y.-Y.; Gao, X.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 9644-9645
26. Yadav, J. S.; Reddy, B. V. S.; Chary, D. N.; Chandrakanth, D. Tetrahedron Lett. 2009, 50, 1136-1138
27. Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560-1638
28. Denmark, S. E.; Collins, W. R. Org. Lett. 2007, 9, 3801
29. Denmark, S. E.; Burk, M. T. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20655-20660
30. Denmark, S. E.; Kalyani, D.; Collins, W. R. J. Am. Chem. Soc. 2010, 132, 15752-15765
31. Mellegaard, S. R; Tunge, J. A. J. Org. Chem. 2004, 69, 8979-8981
32. Balkrishna, S. J.; Prasad, C. D.; Panini, P.; Detty, M. R.; Chopra, D.; Kumar, S. J. Org. Chem. 2012, 77, 9541-9542
33. Denmark, S. E.; Kornfilt, D. J. P.; Vogler, T. J. Am. Chem. Soc. 2011, 133, 15308-15311
34. Snyder, A. S.; Treitler, D. S.; Brucks, A. P. J. Am. Chem. Soc. 2010, 132, 14303-14314
35. Snyder, A. S.; Treitler, D. S.; Brucks, A. P.; Sattler, W. J. Am. Chem. Soc. 2011, 133, 15898-15901
36. Chu, Q.; Wang, Z.; Huang, Q.; Yan, C.; Zhu, S. New J. Chem. 2003, 27, 1522-1527
37. Cinüčić, D.; Friščić, T.; Jones, W. CrystEngComm 2011, 13, 3224-3231
38. Zhou, L.; Tan, C. K.; Jiang, X.; Chen, F.; Yeung, Y.-Y. J. Am. Chem. Soc. 2010, 132, 15474-15476
39. Tan, C. K.; Zhou, L.; Yeung, Y.-Y. Org. Lett. 2011, 13, 2738-2741
40. Zhou, L.; Chen, J.; Tan, C. K.; Yeung, Y.-Y. J. Am. Chem. Soc. 2011, 133, 9164-9167
41. Chen, J.; Zhou, L.; Tan, C. K.; Yeung, Y.-Y. J. Org. Chem. 2012, 77, 999-1009
42. Chen, J.; Zhou, L.; Yeung, Y.-Y. Org. Biomol. Chem. 2012, 10, 3808-3811
43. Tan, C. K.; Le, C.; Yeung, Y.-Y. Chem. Commun. 2012, 48, 5793-5795
44. Jiang, X.; Tan, C. K.; Zhou, L.; Yeung, Y.-Y. Angew. Chem., Int. Ed. 2012, 51, 7771-7775
45. Cheng, Y. A.; Chen, T.; Tan, C. K.; Heng, J. J.; Yeung, Y.-Y. J. Am. Chem. Soc. 2012, 134, 16492-16495
46. Zhou, L.; Tay, D. W.; Chen, J.; Leung, G. Y. C.; Yeung, Y.-Y. Chem. Commun. 2013, Advanced Article, DOI: 10.1039/C2CC36578B.
47. Chen, F.; Tan, C. K.; Yeung, Y.-Y. J. Am. Chem. Soc. 2013, 135, 1232-1235
48. Tan, C. K.; Chen, F.; Yeung, Y.-Y. Tetrahedron Lett. 2011, 52, 4892-4895
49. Brook, M. A.; Hadi, M. A.; Neuy, A. J. Chem. Soc., Chem. Commun. 1989, 957-958
50. Zhang, W.; Stone, J. A.; Brook, M. A.; McGibbon, G. A. J. Am. Chem. Soc. 1996, 118, 5764-5771
51. Detty, M. R.; Friedman, A. E.; Oseroff, A. R. J. Org. Chem. 1994, 59, 8245-8250
52. Detty, M. R. J. Org. Chem. 1980, 45, 274-279