Efficient C(sp3alkyl)-SCF3 bond formations via copper-mediated trifluoromethylthiolation of alkyl halides

Organic and Biomolecular Chemistry

Volumn 12, Issue 29, 2014, Pages 5500-5508

  Lin, Quanfu ^a   Chen, Li ^a   Huang, Yangjie ^a   Rong, Mingguang ^a   Yuan, Yaofeng ^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

FUNCTIONAL GROUPS;

ALKYL HALIDES; BOND FORMATION; THIOETHERS; TRIFLUOROMETHYL;

COPPER;

EID: 84903772571     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c4ob00403e     Document Type: Article

References (61)

1. C. Hansch A. Leo S. H. Unger K. H. Kim D. Nikaitani E. J. Lien J. Med. Chem. 1973 16 1207 1216
2. F. Leroux P. Jeschke M. Schlosser Chem. Rev. 2005 105 827 856
3. A. Becker, Inventory of Industrial Fluoro-Biochemicals, Eyrolles, Paris, 1996
4. B. R. Langlois, T. Billard, S. Large and N. Roques, Fluorinated Bio-active Compounds, Fluorine Technology, Cheshire, 1999, Paper 24
5. V. N. Boiko Beilstein J. Org. Chem. 2010 6 880 921
6. A. Tlili T. Billard Angew. Chem., Int. Ed. 2013 52 6818 6819
7. G. Landelle A. Panossian S. Pazenok J.-P. Vors F. R. Leroux Beilstein J. Org. Chem. 2013 9 2476 2536
8. C. Pooput W. R. Dolbier M. Médebielle J. Org. Chem. 2006 71 3564 3568
9. G. Blond T. Billard B. R. Langlois Tetrahedron Lett. 2001 42 2473 2475
10. N. Roques J. Fluorine Chem. 2001 107 311 314
11. T. Billard B. R. Langlois Tetrahedron Lett. 1996 37 6865 6868
12. U. Teruo I. Sumi Tetrahedron Lett. 1990 31 3579 3582
13. T. Umemoto S. Ishihara J. Am. Chem. Soc. 1993 115 2156 2164
14. I. Kieltsch P. Eisenberger A. Togni Angew. Chem., Int. Ed. 2007 46 754 757
15. C. Wakselman M. Tordeux J. Org. Chem. 1985 50 4047 4051
16. C. Wakselman M. Tordeux J.-L. Clavel B. Langlois J. Chem. Soc., Chem. Commun. 1991 993 994
17. B. Quiclet-Sire R. N. Saicic S. Z. Zard Tetrahedron Lett. 1996 37 9057 9058
18. T. Billard N. Roques B. R. Langlois J. Org. Chem. 1999 64 3813 3820
19. C. Pooput M. Medebielle W. R. Dolbier Org. Lett. 2004 6 301 303
20. A. Harsányi É. Dorkó Á. Csapó T. Bakó C. Peltz J. Rábai J. Fluorine Chem. 2011 132 1241 1246
21. L. M. Yagupolskii N. V. Kondratenko V. P. Sambur Synthesis 1975 721 723
22. D. C. Remy K. E. Rittle C. A. Hunt M. B. Freedman J. Org. Chem. 1976 41 1644 1646
23. Q.-Y. Chen J.-X. Duan J. Chem. Soc., Chem. Commun. 1993 918 919
24. D. J. Adams A. Goddard J. H. Clark D. J. Macquarrie Chem. Commun. 2000 987 988
25. D. J. Adams J. H. Clark J. Org. Chem. 2000 65 1456 1460
26. W. Tyrra D. Naumann B. Hoge Y. L. Yagupolskii J. Fluorine Chem. 2003 119 101 107
27. G. Teverovskiy D. S. Surry S. L. Buchwald Angew. Chem., Int. Ed. 2011 50 7312 7314
28. C. Chen Y. Xie L. Chu R.-W. Wang X. Zhang F.-L. Qing Angew. Chem., Int. Ed. 2012 51 2492 2495
29. C.-P. Zhang D. A. Vicic J. Am. Chem. Soc. 2012 134 183 185
30. C.-P. Zhang D. A. Vicic Chem.-Asian J. 2012 7 1756 1758
31. L. D. Tran I. Popov O. Daugulis J. Am. Chem. Soc. 2012 134 18237 18240
32. Y.-D. Yang A. Azuma E. Tokunaga M. Yamasaki M. Shiro N. Shibata J. Am. Chem. Soc. 2013 135 8782 8785
33. M. Rueping N. Tolstoluzhsky P. Nikolaienko Chem.-Eur. J. 2013 19 14043 14046
34. A. Ferry T. Billard B. R. Langlois E. Bacqué Angew. Chem., Int. Ed. 2009 48 8551 8555
35. A. Ferry T. Billard E. Bacqué B. R. Langlois J. Fluorine Chem. 2012 134 160 163
36. F. Baert J. Colomb T. Billard Angew. Chem., Int. Ed. 2012 51 10382 10385
37. X. Shao X. Wang T. Yang L. Lu Q. Shen Angew. Chem., Int. Ed. 2013 52 3457 3460
38. T. Bootwicha X. Liu R. Pluta I. Atodiresei M. Rueping Angew. Chem., Int. Ed. 2013 52 12856 12859
39. A. A. Kolomeitsev K. Y. Chabanenko G. V. Röschenthaler Y. L. Yagupolskii Synthesis 1994 145 146
40. R. M. DeMarinis J. R. E. Hoover G. L. Dunn P. Actor J. V. Uri J. A. Weisbach J. Antibiot. 1975 28 463 470
41. A. Rudolph M. Lautens Angew. Chem., Int. Ed. 2009 48 2656 2670
42. E. Anselmi J.-C. Blazejewski M. Tordeux C. Wakselman J. Fluorine Chem. 2000 105 41 44
43. T. Billard S. Large B. R. Langlois Tetrahedron Lett. 1997 38 65 68
44. N. V. Ignat'ev V. N. Boiko L. M. Yagupolskii Zh. Org. Khim. 1985 21 653
45. Z. Weng W. He C. Chen R. Lee D. Tan Z. Lai D. Kong Y. Yuan K.-W. Huang Angew. Chem., Int. Ed. 2013 52 1548 1552
46. D. Kong Z. Jiang S. Xin Z. Bai Y. Yuan Z. Weng Tetrahedron 2013 69 6046 6050
47. J. Tan G. Zhang Y. Ou Y. Yuan Z. Weng Chin. J. Chem. 2013 31 921 926
48. P. Zhu X. He X. Chen Y. You Y. Yuan Z. Weng Tetrahedron 2014 70 672 677
49. T. M. Figg M. Wasa J.-Q. Yu D. G. Musaev J. Am. Chem. Soc. 2013 135 14206 14214
50. K. Urgin C. Aubé M. Pipelier V. Blot C. Thobie-Gautier S. Sengmany J. Lebreton E. Léonel D. Dubreuil S. Condon Eur. J. Org. Chem. 2013 117 124
51. S. K. Gurung S. Thapa A. S. Vangala R. Giri Org. Lett. 2013 15 5378 5381
52. H.-F. Duan J.-H. Xie W.-J. Shi Q. Zhang Q.-L. Zhou Org. Lett. 2006 8 1479 1481
53. B. Maillard D. Forrest K. U. Ingold J. Am. Chem. Soc. 1976 98 7024 7026
54. Y. Liu C. Chen H. Li K.-W. Huang J. Tan Z. Weng Organometallics 2013 32 6587 6592
55. Y. Dai F. Wu Z. Zang H. You H. Gong Chem.-Eur. J. 2012 18 808 812
56. P. Ren O. Vechorkin K. v. Allmen R. Scopelliti X. Hu J. Am. Chem. Soc. 2011 133 7084 7095
57. W. L. F. Armerego and C. L. L. Chai, Purification of Laboratory Chemicals, Elsevier, Amsterdam, 6th edn, 2009
58. V. M. Timoshenko C. Portella J. Fluorine Chem. 2009 130 586 590
59. J. W. Cubbage Y. Guo R. D. McCulla W. S. Jenks J. Org. Chem. 2001 66 8722 8736
60. A. Hasegawa T. Ishikawa K. Ishihara H. Yamamoto Bull. Chem. Soc. Jpn. 2005 78 1401 1410
61. J. B. Hendrickson P. L. Skipper Tetrahedron 1976 32 1627 1635