Electrophilic trifluoromethylthiolation of allylsilanes with trifluoromethanesulfanamide

Organic Letters

Volumn 15, Issue 4, 2013, Pages 894-897

  Liu, Jianbo ^a   Chu, Lingling ^a   Qing, Feng Ling ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b DONGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; FLUORINATED HYDROCARBON; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALLYL COMPOUNDS; CATALYSIS; HYDROCARBONS, FLUORINATED; MOLECULAR STRUCTURE; SILANES; STEREOISOMERISM;

EID: 84873967548     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400032g     Document Type: Article

References (48)

1. Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525
2. Hansch, C.; Leo, A.; Unger, S. H.; Kim, K. H.; Nikaitani, D.; Lien, E. J. J. Med. Chem. 1973, 16, 1207
3. Leroux, F.; Jeschke, P.; Schlosser, M. Chem. Rev. 2005, 105, 827
4. Wakselman, C.; Tordeux, M. J. Org. Chem. 1985, 50, 4047
5. Tordeux, M.; Wakselman, C.; Langlois, B. J. Org. Chem. 1989, 54, 2452
6. Soloshonok, V.; Kukhar, V.; Pastrait, Y.; Nazaretian, V. Synlett 1992, 657
7. Koshechko, V. G.; Kiprianova, L. A.; Fileleeva, L. I. Tetrahedron Lett. 1992, 33, 6677
8. Umemoto, T.; Ishihara, S. J. Am. Chem. Soc. 1993, 115, 2156
9. Billard, T.; Langlois, B. R. Tetrahedron Lett. 1996, 37, 6865
10. Quiclet-Sire, B.; Saicic, R. N.; Zars, S. Z. Tetrahedron Lett. 1996, 37, 9057
11. Billard, T.; Large, S.; Langlois, B. R. Tetrahedron Lett. 1997, 38, 65
12. Billard, T.; Roques, N.; Langlois, B.R. J. Org. Chem. 1999, 64, 3813
13. Large, S.; Roques, N.; Langlois, B. R. J. Org. Chem. 2000, 65, 8848
14. Pooput, C.; Medebielle, M.; Dolbier, W. R. Org. Lett. 2003, 6, 301
15. Pooput, C.; Dolbier, W. R.; Medebielle, M. J. Org. Chem. 2006, 71, 3564
16. Kieltsch, I.; Eisenberger, P.; Togni, A. Angew. Chem., Int. Ed. 2007, 46, 754
17. Harris, J. F.; Stacey, F. W. J. Am. Chem. Soc. 1961, 83, 840
18. Harris, J. F. J. Am. Chem. Soc. 1962, 84, 3148
19. Sheppard, W.; Andreades, S.; Harris, J. F. J. Org. Chem. 1964, 29, 898
20. Harris, J. F. J. Org. Chem. 1966, 31, 931
21. Munavalli, S.; Rohrbaugh, D. K.; Rossman, D. I.; Wagner, W. G.; Durst, H. D. Phosphorus Sulfur Silicon Relat. Elem. 2002, 177, 1021
22. Adams, D. J.; Clark, J. H. J. Org. Chem. 2000, 65, 1456
23. Adams, D. J.; Goddard, A.; Clark, J. H.; Macquarrie, D. J. Chem. Commun. 2000, 987
24. Tyrra, W.; Naumann, D.; Hoge, B.; Yagupolskii, Y. L. J. Fluorine Chem. 2003, 119, 101
25. Chen, Q.-Y.; Duan, J.-X. J. Chem. Soc., Chem. Commun. 1993, 918
26. Teverovskiy, G.; Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 7312
27. Zhang, C.-P.; Vicic, D. A. J. Am. Chem. Soc. 2011, 134, 183
28. Weng, Z.; He, W.; Chen, C.; Lee, R.; Tan, D.; Lai, Z.; Kong, D.; Yuan, Y.; Huang, K.-W. Angew. Chem., Int. Ed. 2013, 52, 1548
29. Chen, C.; Xie, Y.; Chu, L.; Wang, R.-W.; Zhang, X.; Qing, F.-L. Angew. Chem., Int. Ed. 2012, 51, 2492
30. Zhang, C.-P.; Vicic, D. A. Chem.-Asian J. 2012, 7, 1756
31. Chen, C.; Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2012, 134, 12454
32. Sheppard, W. A. J. Org. Chem. 1964, 29, 895
33. Bogdanowicz-Szwed, K.; Kawalek, B.; Lieb, M. J. Fluorine Chem. 1987, 35, 317
34. Tran, L. D.; Popov, I.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 18237
35. Ferry, A. l.; Billard, T.; Langlois, B. R.; Bacqué, E. J. Org. Chem. 2008, 73, 9362
36. Ferry, A.; Billard, T.; Langlois, B. R.; Bacqué, E. Angew. Chem., Int. Ed. 2009, 48, 8551
37. Ferry, A.; Billard, T.; Bacqué, E.; Langlois, B. R. J. Fluorine Chem. 2012, 134, 160
38. Baert, F.; Colomb, J.; Billard, T. Angew. Chem., Int. Ed. 2012, 51, 10382
39. Yang, Y.; Jiang, X.; Qing, F.-L. J. Org. Chem. 2012, 77, 7538
40. Kirsch, P. Modern Fluoroorganic Chemistry; Wiley-VCH: Weinheim, 2004.
41. Uneyama, K. Organofluorine Chemistry; Blackwell Publishing: Oxford, 2006.
42. Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305
43. Parsons, A. T.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 9120
44. Xu, J.; Fu, Y.; Luo, D. F.; Jiang, Y. Y.; Xiao, B.; Liu, Z. J.; Gong, T. J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 15300
45. Wang, X.; Ye, Y.; Zhang, S.; Feng, J.; Xu, Y.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 16410
46. Chu, L.; Qing, F.-L. Org. Lett. 2012, 14, 2106
47. Shimizu, R.; Egami, H.; Hamashima, Y.; Sodeoka, M. Angew. Chem., Int. Ed. 2012, 51, 4577
48. Mizuta, S.; Galicia-López, O.; Engle, K. M.; Verhoog, S.; Wheelhouse, K.; Rassias, G.; Gouverneur, V. Chem.-Eur. J. 2012, 18, 8583