Synthesis of vinyl trifluoromethyl thioethers via copper-mediated trifluoromethylthiolation of vinyl bromides

Journal of Organic Chemistry

Volumn 80, Issue 5, 2015, Pages 2912-2917

  Huang, Yangjie ^a   Ding, Jianping ^a   Wu, Chuyi ^a   Zheng, Huidong ^a   Weng, Zhiqiang ^a,b  

^a FUZHOU UNIVERSITY   (China)

^b FUJIAN INSTITUTE OF RESEARCH ON THE STRUCTURE OF MATTER   (China)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; FUNCTIONAL GROUPS;

HETEROCYCLIC GROUPS; HIGH YIELD; THIOETHERS; TRIFLUOROMETHYL; VINYL BROMIDES;

SYNTHESIS (CHEMICAL);

BROMINE DERIVATIVE; COPPER; FLUORINE; HALIDE; SULFIDE; FLUORINATED HYDROCARBON; HALOGEN; HETEROCYCLIC COMPOUND; NITRILE; VINYL BROMIDE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION TIME; REDUCTION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE; TRIFLUOROMETHYLTHIOLATION; CATALYSIS; CHEMISTRY;

CATALYSIS; COPPER; HALOGENS; HETEROCYCLIC COMPOUNDS; HYDROCARBONS, FLUORINATED; NITRILES; SULFIDES; VINYL COMPOUNDS;

EID: 84924308574     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00144     Document Type: Article

References (44)

1. Kirsch, P. Modern fluoroorganic chemistry: synthesis, reactivity, applications; Wiley-VCH: Weinheim, 2004.
2. Ojima, I., Ed. Fluorine in Medicinal Chemistry and Chemical Biology; John Wiley & Sons Ltd.: 2009.
3. Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432
4. Zhu, W.; Wang, J.; Wang, S.; Gu, Z.; Aceña, J. L.; Izawa, K.; Liu, H.; Soloshonok, V. A. J. Fluorine Chem. 2014, 167, 37
5. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165
6. Tlili, A.; Billard, T. Angew. Chem., Int. Ed. 2013, 52, 6818
7. Toulgoat, F.; Alazet, S.; Billard, T. Eur. J. Org. Chem. 2014, 2415
8. Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513
9. Wang, H.; Vicic, D. A. Synlett 2013, 24, 1887
10. He, W.; Weng, Z. Prog. Chem. 2013, 25, 1071
11. Xu, X.-H.; Matsuzaki, K.; Shibata, N. Chem. Rev. 2015, 115, 731
12. Chen, C.; Xie, Y.; Chu, L.; Wang, R.-W.; Zhang, X.; Qing, F.-L. Angew. Chem., Int. Ed. 2012, 51, 2492
13. Zhang, C.-P.; Vicic, D. A. Chem. - Asian J. 2012, 7, 1756
14. Pluta, R.; Nikolaienko, P.; Rueping, M. Angew. Chem., Int. Ed. 2014, 53, 1650
15. Shao, X.; Liu, T.; Lu, L.; Shen, Q. Org. Lett. 2014, 16, 4738
16. Xu, J.; Mu, X.; Chen, P.; Ye, J.; Liu, G. Org. Lett. 2014, 16, 3942
17. Danoun, G.; Bayarmagnai, B.; Gruenberg, M. F.; Goossen, L. J. Chem. Sci. 2014, 5, 1312
18. Tran, L. D.; Popov, I.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 18237
19. Xu, C.; Ma, B.; Shen, Q. Angew. Chem., Int. Ed. 2014, 53, 9316
20. Chen, C.; Xu, X.-H.; Yang, B.; Qing, F.-L. Org. Lett. 2014, 16, 3372
21. Xu, C.; Shen, Q. Org. Lett. 2014, 16, 2046
22. Hu, F.; Shao, X.; Zhu, D.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2014, 53, 6105
23. Teverovskiy, G.; Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 7312
24. Zhang, C.-P.; Vicic, D. A. J. Am. Chem. Soc. 2012, 134, 183
25. Shao, X.; Wang, X.; Yang, T.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2013, 52, 3457
26. Rueping, M.; Tolstoluzhsky, N.; Nikolaienko, P. Chem. - Eur. J. 2013, 19, 14043
27. Bates, C. G.; Saejueng, P.; Doherty, M. Q.; Venkataraman, D. Org. Lett. 2004, 6, 5005
28. Zheng, Y.; Du, X.; Bao, W. Tetrahedron Lett. 2006, 47, 1217
29. Kabir, M. S.; Van Linn, M. L.; Monte, A.; Cook, J. M. Org. Lett. 2008, 10, 3363
30. Kabir, M. S.; Lorenz, M.; Van Linn, M. L.; Namjoshi, O. A.; Ara, S.; Cook, J. M. J. Org. Chem. 2010, 75, 3626
31. Kao, H.-L.; Lee, C.-F. Org. Lett. 2011, 13, 5204
32. Xu, R.-S.; Yue, L.; Pan, Y.-J. Tetrahedron 2012, 68, 5046
33. 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
34. Kong, D.; Jiang, Z.; Xin, S.; Bai, Z.; Yuan, Y.; Weng, Z. Tetrahedron 2013, 69, 6046
35. Tan, J.; Zhang, G.; Ou, Y.; Yuan, Y.; Weng, Z. Chin. J. Chem. 2013, 31, 921
36. Zhu, P.; He, X.; Chen, X.; You, Y.; Yuan, Y.; Weng, Z. Tetrahedron 2014, 70, 672
37. Lin, Q.; Chen, L.; Huang, Y.; Rong, M.; Yuan, Y.; Weng, Z. Org. Biomol. Chem. 2014, 12, 5500
38. Hou, C.; Lin, X.; Huang, Y.; Chen, Z.; Weng, Z. Synthesis 2015, 47, doi: 10.1055/s-0034-1379972.
39. Cohen, T.; Cristea, I. J. Am. Chem. Soc. 1976, 98, 748
40. Telvekar, V. N.; Arote, N. D.; Herlekar, O. P. Synlett 2005, 2495
41. Fursule, R. A.; Patil, P. O.; Shewale, B. D.; Kosalge, S. B.; Deshmukh, P. K.; Patil, D. A. Chem. Pharm. Bull. 2009, 57, 1243
42. Kaloko, J.; Hayford, A. Org. Lett. 2005, 7, 4305
43. Cheung, L. L. W.; Yudin, A. K. Org. Lett. 2009, 11, 1281
44. Adams, D. J.; Clark, J. H. J. Org. Chem. 2000, 65, 1456