Fluoride ion-mediated nucleophilic fluoroalkylation of alkyl halides with Me3SiCF2SPh: Synthesis of PhSCF2- and CF2H-containing compounds

Journal of Fluorine Chemistry

Volumn 129, Issue 5, 2008, Pages 382-385

  Li, Ya ^a   Hu, Jinbo ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

(Phenylthio)difluoromethylation; Alkyl halides; Difluoromethylation; Nucleophilic substitution; Selective fluoroalkylation

Indexed keywords

EID: 42049101428     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2008.01.010     Document Type: Article

References (34)

1. Biomedical Frontiers of fluorine chemistry. In: Ojima I., McCarthy J.R., and Welch J.T. (Eds). ACS Symposium Series 639. ACS, Washington, DC (1996)
2. In: Filler R., Kobayashi Y., and Yagupolskii L.M. (Eds). Organofluorine Compounds in Medicinal Chemistry and Biomedicinal Applications (1993), Elsevier, Amsterdam
3. In: Welch J.T., and Eswarakrishnan S. (Eds). Fluorine in Bioorganic Chemistry (1991), Wiley, New York
4. Uneyama K. Organofluorine Chemistry (2006), Blackwell, New Delhi
5. Kirsch P. Modern Fluoroorganic Chemistry (2004), Wiley-VCH, Weinheim
6. Chambers R.D. Fluorine in Organic Chemistry (2004), Blackwell, Oxford
7. Hiyama T. Organofluorine Compounds: Chemistry and Applications (2000), Springer, New York
8. Muller K., Fash C., and Diederich F. Science 317 (2007) 1881-1886
9. Thayer A.M. Chem. Eng. News 84 23 (2006) 15-24 pp. 27-32
10. Prakash G.K.S., Yudin A.K., Deffieux D., Bradley M., Bau R., and Olah G.A. J. Am. Chem. Soc. 119 (1997) 1572-1581 (and the references cited therein)
11. Erickson J.A., and McLoughlin J.I. J. Org. Chem. 60 (1995) 1626-1631
12. Sasson R., Hagooly A., and Rozen S. Org. Lett. 5 (2003) 769-771
13. Prakash G.K.S., Hu J., Wang Y., and Olah G.A. Org. Lett. 6 (2004) 4315-4317
14. Li Y., and Hu J. Angew. Chem. Int. Ed. 44 (2005) 5882-5886
15. Prakash G.K.S., Weber C., Chacko S., and Olah G.A. Org. Lett. 9 (2007) 1863-1866
16. Prakash G.K.S., Hu J., Wang Y., and Olah G.A. Org. Lett. 6 (2004) 4315-4317 (and the references cited therein)
17. Middleton W.J. J. Org. Chem. 40 (1975) 574-578
18. Olah G.A., Nojima M., and Kerekes I. J. Am. Chem. Soc. 96 (1974) 925-927
19. Martinez G.A., Barcina O.J., Rys A.Z., and Subramanian L.R. Tetrahedron Lett. 33 (1992) 7787-7788
20. Sondej S.C., and Katzenellenbogen J.A. J. Org. Chem. 51 (1986) 3508-3513
21. In: Olah G.A., Chambers R.D., and Prakash G.K.S. (Eds). Synthetic Fluorine Chemistry (1992), Wiley, New York
22. Gonzales J., Foti C.J., and Elsheimer S. J. Org. Chem. 56 (1991) 4322-4325
23. Langlois B.R. J. Fluorine Chem. 41 (1988) 247-261
24. Hagiwara T., and Fuchikami T. Synlett (1995) 717-718
25. Prakash G.K.S., and Hu J. Acc. Chem. Res. 40 (2007) 921-930 (and the references cited therein)
26. Tyrra W., Naumann D., Quadt S., Buslei S., Yagupolskii Y.L., and Kremlev M.M. J. Fluorine Chem. 128 (2007) 813-817
27. 2SPh (1):
28. Prakash G.K.S., Hu J., and Olah G.A. J. Org. Chem. 68 (2003) 4457-4463
29. Prakash G.K.S., Hu J., Wang Y., and Olah G.A. J. Fluorine Chem. 126 (2005) 529-534
30. Pohmakotr M., Boonkitpattarakul K., Ieawsuwan W., Jarussophon S., Duangdee N., Tuchinda P., and Reutrakul V. Tetrahedron 62 (2006) 5973-5985
31. Mizuta S., Shibata N., Ogawa S., Fujimoto H., Nakamura S., and Toru T. Chem. Commun. (2006) 2575-2577
32. Li Y., and Hu J. Angew. Chem. Int. Ed. 46 (2007) 2489-2494
33. Pohmakotr M., Panichakul D., Tuchinda P., and Reutrakul V. Tetrahedron 63 (2007) 9429-9436
34. Toulgoat F., Langlois B.R., Medebielle M., and Sanchez J.-Y. J. Org. Chem. 72 (2007) 9046-9052