Copper-Catalyzed Intermolecular Trifluoromethylthiocyanation of Alkenes: Convenient Access to CF3-Containing Alkyl Thiocyanates

Organic Letters

Volumn 17, Issue 10, 2015, Pages 2438-2441

  Liang, Zhaoli ^a   Wang, Fei ^a   Chen, Pinhong ^a   Liu, Guosheng ^a  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; COPPER; FLUORINATED HYDROCARBON; THIOCYANIC ACID DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKENES; CATALYSIS; COPPER; HYDROCARBONS, FLUORINATED; MOLECULAR STRUCTURE; THIOCYANATES;

EID: 84929573535     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00939     Document Type: Article

References (53)

1. Grishchuk, B. D.; Prodanchuk, N. G.; Sinchenko, V. G.; Gorbovoi, P. M.; Kudrik, E. Y. Pharm. Chem. J. 1994, 28, 657
2. Long, J. K.; Hanagan, M. A.; Marshall, E. A.; Sharpe, P. L.; Ding, A. X. WO 2012/030922A1, 2012.
3. Szajnman, S. H.; Yan, W.; Bailey, B. N.; Docampo, R.; Elhalem, E.; Rodriguez, J. B. J. Med. Chem. 2000, 43, 1826
4. Wood, J. L. Org. React. 1946, 3, 240
5. Kelly, T. R.; Kim, M. H.; Curtis, A. D. M. J. Org. Chem. 1993, 58, 5855
6. Lehmkuhl, H.; Rabet, F.; Hauchild, K. Synthesis 1977, 184
7. Ando, T.; Clark, J. H.; Cork, D. G.; Fujita, M.; Kimura, T. J. Org. Chem. 1987, 52, 681
8. Kiasat, A. R.; Badri, R.; Sayyahi, S. Chin. Chem. Lett. 2008, 19, 1301
9. Gorjizadeh, M.; Sayyahi, S. Chin. Chem. Lett. 2011, 22, 659
10. Tamura, Y.; Kawasaki, T.; Adachi, M.; Tanio, M.; Kita, Y. Tetrahedron Lett. 1977, 18, 4417
11. Iranpoor, N.; Firouzabadi, H.; Shaterian, H. R. J. Chem. Res.(S) 1999, 676
12. Mokhtari, B.; Azadi, R.; Nezhad, S. R. Tetrahedron Lett. 2009, 50, 6588
13. Khazaei, A.; Rahmati, S.; Nezhad, A. K.; Saednia, S. J. Fluorine Chem. 2012, 137, 123
14. Guram, A. S. Synlett 1993, 259
15. Prakash, O.; Kaur, H.; Batra, H.; Rani, N.; Singh, S. P.; Moriarty, R. M. J. Org. Chem. 2001, 66, 2019
16. Kumar, A.; Ahamd, P.; Maurya, R. A. Tetrahedron Lett. 2007, 48, 1399
17. Wu, D. Z.; Yang, X. J.; Wu, L. Q. J. Chem. Sci. 2012, 124, 901
18. Hiyama, T. Organofluorine Compounds: Chemistry and Applications; Springer: Berlin, 2000.
19. Ojima, I. Fluorine in Medical Chemistry and Chemical Biology; Wiley-Blackwell: Chichester, U.K., 2009.
20. Jeschke, P. ChemBioChem 2004, 5, 570
21. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
22. 3 formation, see: Parsons, A. T.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 9120
23. Xu, J.; Fu, Y.; Luo, D.; Jiang, Y.; Xiao, B.; Liu, Z.; Gong, T.; Liu, L. J. Am. Chem. Soc. 2011, 133, 15300
24. Wang, X.; Ye, Y.; Zhang, S.; Feng, J.; Xu, Y.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 16410
25. Shimizu, R.; Egami, H.; Hamashima, Y.; Sodeoka, M. Angew. Chem., Int. Ed. 2012, 51, 4577
26. Chu, L.; Qing, F. Org. Lett. 2012, 14, 2106
27. For recent reviews on trifluoromethylation of alkenes, see: Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8950
28. Chen, P.; Liu, G. Synthesis 2013, 2919
29. Merino, E.; Nevado, C. Chem. Soc. Rev. 2014, 43, 6598
30. For recent trifluoromethylation of alkenes, see: Janson, P. G.; Ghoneim, I.; IIchenko, N. O.; Szabó, K. J. Org. Lett. 2012, 14, 2882
31. Li, Y.; Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8221
32. Yasu, Y.; Koike, T.; Akita, M. Angew. Chem., Int. Ed. 2012, 51, 9567
33. Zhu, R.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 12462
34. Feng, C.; Loh, T.-P. Chem. Sci. 2012, 3, 3458
35. Mizuta, S.; Verhoog, S.; Engle, K. M.; Khotavivattana, T.; O'Duill, M.; Wheelhouse, K.; Rassias, G.; Médebielle, M.; Gouverneur, V. J. Am. Chem. Soc. 2013, 135, 2505
36. Wu, X.; Chu, L.; Qing, F. Angew. Chem., Int. Ed. 2013, 52, 2198
37. Egami, H.; Shimizu, R.; Kawamura, S.; Sodeoka, M. Angew. Chem., Int. Ed. 2013, 52, 4000
38. Egami, H.; Kawamura, S.; Miyazaki, A.; Sodeoka, M. Angew. Chem., Int. Ed. 2013, 52, 7841
39. Feng, C.; Loh, T.-P. Angew. Chem., Int. Ed. 2013, 52, 12414
40. Egami, H.; Shimizu, R.; Usui, Y.; Sodeoka, M. Chem. Commun. 2013, 49, 7346
41. Egami, H.; Shimizua, R.; Sodeoka, M. J. Fluorine Chem. 2013, 152, 51
42. Liu, X.; Xiong, F.; Huang, X.; Xu, L.; Li, P.; Wu, X. Angew. Chem., Int. Ed. 2013, 52, 6962
43. Chen, Z.-M.; Bai, W.; Wang, S.-H.; Yang, B.-M.; Tu, Y.-Q.; Zhang, F.-M. Angew. Chem., Int. Ed. 2013, 52, 9781
44. Ilchenko, N. O.; Janson, P. G.; Szabó, K. J. J. Org. Chem. 2013, 78, 11087
45. He, Y.-T.; Li, L.-H.; Yang, Y.-F.; Zhou, Z.-Z.; Hua, H.-L.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2014, 16, 270
46. Zhu, R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2013, 52, 12655
47. Ling, L.; Liu, K.; Li, X.; Li, Y. ACS Catal. 2015, 5, 2458
48. Kawamura, S.; Egami, H.; Sodeoka, M. J. Am. Chem. Soc. 2015, 137, 4865
49. Wang, F.; Qi, X.; Liang, Z.; Chen, P.; Liu, G. Angew.Chem., Int. Ed. 2014, 53, 1881
50. Wang, F.; Wang, D.; Mu, X.; Chen, P.; Liu, G. J. Am. Chem. Soc. 2014, 136, 10202
51. Liang, Z.; Wang, F.; Chen, P.; Liu, G. J. Fluorine Chem. 2014, 167, 55
52. The reaction monitored by NMR undergoes the initial trifluoromethylthiocyanation to give the C-S bond exclusively and then gradually converted to the C-N bond. For the related reports, see: Smith, P. S.; Emerson, D. W. J. Am. Chem. Soc. 1960, 82, 3076
53. Metzger, J. V. In Comprehensive Heterocyclic Chemistry; Katritzky, A., Ed.; Pergamon: Oxford, 1984; Vol. 6, p 235.