Electrophilic (phenylsulfonyl)difluoromethylation of thiols with a hypervalent iodine(III)-CF2SO2Ph reagent

Tetrahedron Letters

Volumn 49, Issue 34, 2008, Pages 5006-5008

  Zhang, Wei ^a   Zhu, Jieming ^a   Hu, Jinbo ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Elctrophilic fluoroalkylation; Fluorine; Hypervalent iodine compound

Indexed keywords

FLUORINE DERIVATIVE; IODINE DERIVATIVE; REAGENT; THIOPHENOL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; FLUORINE NUCLEAR MAGNETIC RESONANCE; METHYLATION; TEMPERATURE;

EID: 46949104968     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.06.064     Document Type: Article

References (35)

1. Smart B.E. J. Fluorine Chem. 122 (2003) 1
2. Müller K., Faeh C., and Diederich F. Science 317 (2007) 1881
3. Thayer A.M. Chem. Eng. News 84 (2006) 15-24 27-32
4. In: Hiyama T. (Ed). Organofluorine Compounds: Chemistry and Applications (2000), Springer, New York
5. In: Banks R.E., Smart B.E., and Tatlow J.C. (Eds). Organofluorine Chemistry: Principles and Commercial Applications (1994), Plenum, New York
6. Uneyama K. Organofluorine Chemistry (2006), Blackwell, Oxford
7. Kirsch P. Modern Fluoroorganic Chemistry (2004), Wiley-VCH, Weinheim
8. Chambers R.D. Fluorine in Organic Chemistry (2004), Blackwell, Oxford
9. In: Soloshonok V.A. (Ed). Fluorine-Containing Synthons (2005), ACS, Washington, DC
10. Ma J.-A., and Cahard D. J. Fluorine Chem. 128 (2007) 975-996
11. Ma J.-A., and Cahard D. Chem. Rev. 104 (2004) 6119-6146
12. Umemoto T. Chem. Rev. 96 (1996) 1757-1778 and references cited therein
13. Yagulpol'skii L.M., Maletina I.I., Kondratenko N.V., and Orda V.V. Synthesis (1978) 835-837
14. Yagulpol'skii L.M., Kondratenko N.V., and Timofeeva G.N. Zh. Org. Khim. 20 (1984) 115-118
15. Umemoto T., and Ishihara S. J. Am. Chem. Soc. 115 (1993) 2156-2164
16. Umemoto T. J. Fluorine Chem. 105 (2000) 211-213
17. Yang J.-J., Kirchmeier R.L., and Shreeve J.M. J. Org. Chem. 63 (1998) 2656-2660
18. Magnier E., Blazejewski J.-C., Tordeux M., and Wakselman C. Angew. Chem., Int. Ed. 45 (2006) 1279-1282
19. Prakash G.K.S., Weber C., Chacko S., and Olah G.A. Org. Lett. 9 (2007) 1863-1866
20. Prakash G.K.S., Ledneczki I., Chacko S., and Olah G.A. Org. Lett. 10 (2008) 557-560
21. Prakash G.K.S., Weber C., Chacko S., and Olah G.A. J. Comb. Chem. 9 (2007) 920-923
22. Adachi, K.; Ishihara, S. JP 20030388769, 2003.
23. Zhang W., Zhu L., and Hu J. Tetrahedron 63 (2007) 10569-10575
24. Eisenberger P., Gischig S., and Togni A. Chem. Eur. J. 12 (2006) 2579-2586
25. Kieltsch I., Eisenberger P., and Togni A. Angew. Chem., Int. Ed. 46 (2007) 754
26. Eisenberger P., Kieltsch I., Armanino N., and Togni A. Chem. Commun. (2008) 10.1039/b801424h
27. See a recent review:. Prakash G.K.S., and Hu J. Acc. Chem. Res. 40 (2007) 921-930
28. Li Y., and Hu J. Angew. Chem., Int. Ed. 44 (2005) 5882-5886
29. Ni C., and Hu J. Tetrahedron Lett. 46 (2005) 8273-8277
30. Ni C., Liu J., Zhang L., and Hu J. Angew. Chem., Int. Ed. 46 (2007) 786-789
31. Liu J., Ni C., Wang F., and Hu J. Tetrahedron Lett. 49 (2008) 1605-1608
32. Li Y., Liu J., Zhang L., Zhu L., and Hu J. J. Org. Chem. 72 (2007) 5824-5827
33. 3S: C, 42.49; H, 3.34. Found: C, 42.74; H, 3.58.
34. +, 0.26), 159 (100.00). The characterization data was consistent with the previous report, see: Stahly, G. P. J. Fluorine Chem. 1989, 43, 53.
35. 2 was consistent with the previous report, see:. Weigert F.J. J. Org. Chem. 45 (1980) 3476-3483