Nucleophilic tetrafluoroethylation of carbonyl compounds with fluorinated sulfones

Journal of Fluorine Chemistry

Volumn 169, Issue , 2015, Pages 24-31

  Václavík, Jiří ^a,b   Chernykh, Yana ^a   Jurásek, Bronislav ^a,b   Beier, Petr ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

Carbonyl compounds; Fluorine; Nucleophilic addition; Sulfones; Tetrafluoroethylation

Indexed keywords

EID: 84922248628     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2014.10.019     Document Type: Article

References (44)

1. E.A. Ilardi, E. Vitaku, and J.T. Njardarson J. Med. Chem. 57 2014 2832
2. G. Theodoridis Fluorine-containing agrochemicals: an overview of recent developments A. Tressaud, Fluorine and the Environment Agrochemicals, Archaeology, Green Chemistry & Water vol. 2 2006 Elsevier Oxford 121 175
3. X. Liu, C. Xu, M. Wang, and Q. Liu Chem. Rev. 2014 10.1021/cr400473a
4. G.K.S. Prakash, J. Hu, and G.A. Olah Org. Lett. 5 2003 3253
5. G.K.S. Prakash, and A.K. Yudin Chem. Rev. 97 1997 757
6. G.K.S. Prakash, and M. Mandal J. Fluorine Chem. 112 2001 123
7. R.P. Singh, and J.M. Shreeve Tetrahedron 56 2000 7613
8. K. Uneyama, T. Katagiri, and H. Amii Acc. Chem. Res. 41 2008 817
9. J.-A. Ma, and D. Cahard Chem. Rev. 108 2008 1
10. D.Y. Mikhaylov, and Y.H. Budnikova Russ. Chem. Rev. 82 2013 835
11. W.R. Dolbier Chem. Rev. 96 1996 1557
12. Y. Li, and A. Studer Angew. Chem. Int. Ed. 51 2012 8221
13. Y. Ji, T. Brueckl, R.D. Baxter, Y. Fujiwara, I.B. Seiple, S. Su, D.G. Blackmond, and P.S. Baran Proc. Natl. Acad. Sci. U. S. A. 108 2011 14411
14. Y. Macé, and E. Magnier Eur. J. Org. Chem. 2012 2479
15. J. Charpentier, N. Früh, and A. Togni Chem. Rev. 2014 10.1021/cr500223h
16. N. Shibata, A. Matsnev, and D. Cahard Beilstein J. Org. Chem. 6 65 2010
17. T. Liang, C.N. Neumann, and T. Ritter Angew. Chem. Int. Ed. 52 2013 8214
18. G.K.S. Prakash, and J. Hu Acc. Chem. Rev. 40 2007 921
19. C.-M. Hu, and Y.-L. Qiu J. Fluorine Chem. 55 1991 109
20. C.-M. Hu, Y.-L. Qiu, and F.-L. Qing J. Fluorine Chem. 51 1991 295
21. C.-M. Hu, and Y.-L. Qiu J. Chem. Soc., Perkin Trans. 1 1992 1569
22. C.-M. Hu, and Y.-L. Qiu J. Chem. Soc. 1 1993 331
23. Z.-Y. Long, and Q.-Y. Chen J. Org. Chem. 64 1999 4775
24. R.S. Timofte, and B. Linclau Org. Lett. 10 2008 3673
25. E.G. Locke, W.R. Brode, and A.L. Henne J. Am. Chem. Soc. 56 1934 1726
26. Q.-Y. Chen, and Z.-M. Qiu J. Fluorine Chem. 35 1987 343
27. R.N. Haszeldine J. Chem. Soc. 1952 4423
28. Y. Chernykh, K. Hlat-Glembová, B. Klepetářová, and P. Beier Eur. J. Org. Chem. 2011 4528
29. Y. Chernykh, S. Opekar, B. Klepetářová, and P. Beier Synlett 23 2012 1187
30. Y. Chernykh, and P. Beier J. Fluorine Chem. 156 2013 307
31. Y. Chernykh, B. Jurásek, and P. Beier J. Fluorine Chem. 2014 10.1016/j.jfluchem.2014.08.004 (in press)
32. R.C. Besra, S. Rudrawar, and A.K. Chakraborti Tetrahedron Lett. 46 2005 6213
33. H. Yoshida, H. Fukushima, T. Morishita, J. Ohshita, and A. Kunai Tetrahedron 63 2007 4793
34. S. Bhagat, and A.K. Chakraborti J. Org. Chem. 73 2008 6029
35. Y. Zhao, J. Zhu, C. Ni, and J. Hu Synthesis 2010 1899
36. J.T. Groves, and K.W. Ma J. Am. Chem. Soc. 96 1974 6527
37. C. Yang, and C.U. Pittman Tetrahedron Lett. 38 1997 6561
38. T. Lund, B. Lundgren, and H. Lund Acta Chem. Scand. 49 1995 755
39. F. Toulgoat, B.R. Langlois, M. Médebielle, and J.-Y. Sanchez J. Org. Chem. 72 2007 9046
40. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09, Revision D.01 2013 Gaussian, Inc. Wallingford, CT
41. D.J. Feller Comp. Chem. 17 1996 1571
42. K.L. Schuchardt, B.T. Didier, T. Elsethagen, L. Sun, V. Gurumoorthi, J. Chase, J. Li, and T.L. Windus J. Chem. Inf. Model. 47 2007 1045
43. F.R. Weigend, and R. Ahlrichs Phys. Chem. Chem. Phys. 7 2005 3297
44. J. Tomasi, B. Mennucci, and R. Cammi Chem. Rev. 105 2005 2999