Radical Addition of Perfluoroalkyl Iodides to Alkenes and Alkynes Initiated by Sodium Dithionite in an Aqueous Solution in the Presence of a Novel Fluorosurfactant
Zhiwei Xiao
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorHuawei Hu
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorJiaoli Ma
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Qingyun Chen
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Tel.: 0086-021-54925462; Fax: 0086-021-64166128Search for more papers by this authorCorresponding Author
Yong Guo
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Tel.: 0086-021-54925462; Fax: 0086-021-64166128Search for more papers by this authorZhiwei Xiao
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorHuawei Hu
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorJiaoli Ma
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorCorresponding Author
Qingyun Chen
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Tel.: 0086-021-54925462; Fax: 0086-021-64166128Search for more papers by this authorCorresponding Author
Yong Guo
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Tel.: 0086-021-54925462; Fax: 0086-021-64166128Search for more papers by this authorAbstract
A new fluorinated anionic surfactant Cl(CF2)6O(CF2)2SO3N(C2H5)4 was prepared and characterized. The application of the fluorosurfactant allowed the fluoroalkylation to occur in the water without adding organic solvent. The addition of perfluoroalkyl iodides with olefins and alkynes under the initiation of Na2S2O4 in water in the presence of the fluorosurfactant gave the corresponding adducts in good to excellent yields. The fluorosurfactant was suitable for a radical addition process.
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REFERENCES
- 1
Chambers, R. D.,
Fluorine in Organic Chemistry, Blackwell Publishing Ltd./CRC Press, Boca Raton, FL, 2004.
10.1002/9781444305371 Google Scholar
- 2
Ojima, I.,
Flourine in Medicinal Chemistry and Chemical Biology, Wiley, Chichester, U. K., 2009.
10.1002/9781444312096 Google Scholar
- 3
Hiyama, T.,
Organofluorine Compounds, Chemistry and Applications, Springer-Verlag, Berlin, 2000.
10.1007/978-3-662-04164-2 Google Scholar
- 4
Kirsch, P.,
Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2004.
10.1002/352760393X Google Scholar
- 5
Uneyama, K.,
Organofluorine Chemistry, Blackwell Publishing, Oxford, 2006.
10.1002/9780470988589 Google Scholar
- 6
Begue, J. P.;
Bonnet-Delpon, D.,
Bioorganic and Medical Chemistry of Fluorine, Wiley, Hoboken, NJ, 2008.
10.1002/9780470281895 Google Scholar
- 7 Muller, K.; Faeh, C.; Diederich, F.. Science, 2007, 317, 1881.
- 8 Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V.. Chem. Soc. Rev., 2008, 37, 320.
- 9 Kirk, K. L.. Org. Proc. Res. Dev., 2008, 12, 305.
- 10 O′Hagan, D.. J. Fluorine Chem., 2010, 131, 1071.
- 11
Handbook of Fluorous Chemistry,
Eds.: J. A. Gladysz; D. P. Curran; I. T. Horváth, Wiley-VCH, Weinheim, 2004.
10.1002/3527603905 Google Scholar
- 12 Huang, B.-N.; Huang, W.-Y.; Hu, C.-M.. Acta Chim. Sinica, 1981, 39, 481.
- 13 Huang, W.-Y.; Huang, B.-N.; Hu, C.-M.. J. Fluorine Chem., 1983, 23, 193.
- 14 Huang, W.-Y.; Huang, B.-N.; Wang, W.. Acta Chim. Sinica, 1983, 41, 1193.
- 15 Huang, B.-N.; Wang, B.-H.; Wang, W.; Huang, W.-Y.. Acta Chim. Sinica, 1985, 43, 1167.
- 16 Huang, W.-Y.; Lv, L.. Chin. J. Chem., 1992, 10, 268.
- 17 Huang, W.-Y.; Zhang, H.-Z.. Chin. J. Chem., 1992, 10, 274.
- 18 Furin, G. G.. Russ. Chem. Rev., 2000, 69, 491.
- 19 Zhang, C.-P.; Chen, Q.-Y.; Guo, Y.; Xiao, J.-C.; Gu, Y.-C.. Chem. Soc. Rev., 2012, 41, 4536.
- 20 Qi, Q.; Shen, Q.; Lv, L.. J. Fluorine Chem., 2012, 133, 115.
- 21 Tang, X.; Chen, Q.-Y.. Chem. Sci., 2012, 3, 1694.
- 22 Sebastián, B.-V.; Al, P.. Eur. J. Org. Chem., 2012, 1889.
- 23 Nguyen, J. D.; Tucker, J. W.; Konieczynska, M. D.; Stephenson, C. R. J.. J. Am. Chem. Soc., 2011, 133, 4160.
- 24 Sebastián, B.-V.; Al, P.. J. Org. Chem., 2010, 75, 6141.
- 25 Al, P.. Can. J. Chem., 2012, 90, 493.
- 26 Kissa, E., Fluorinated Surfactants. Synthesis, Properties, Applications, Marcel Dekker, New York, 1994.
- 27 Gloeckner, V.; Lunkwitz, K.; Prescher, D.. Tenside Surfact. Deterg., 1989, 26, 376.
- 28 Krafft, M.-P.; Riess, J. G.. J. Polym. Sci., Part A: Polym. Chem., 2007, 45, 1185.
- 29 Kaplanek, R.; Paleta, O.; Ferjentsikova, I.; Kodicek, M.. J. Fluorine Chem., 2009, 130, 308.
- 30 Kannan, K.; Corsolini, S.; Falandysz, J.. Enviorn. Sci. Technol., 2004, 38, 4489.
- 31 Cariton, K.; Natalia, V.; Frank, M. B.. J. Environ. Monitor., 2004, 6, 540.
- 32 Inoue, K.; Okada, F.. Environ. Health. Persp., 2004, 112, 1204.
- 34 Zsuzsanna, K.; Larry, L. N.; Antonia, M. C.. Anal. Chem., 2005, 77, 6085.
- 35a Guangming Electroplating Factory, Shanghai Institute of Organic Chemistry, and Taizhou Electrochemical Factory, Acta Chim. Sinica, 1977, 35, 209.
- 35b The Perfluorosulfonic Acid Group, Shanghai Institute of Organic Chemistry, Sci. Sinica, 1978, 21, 773.
- 35c The Perfluorosulfonic Acid Group, Shanghai Institute of Organic Chemistry, Acta Chim. Sinica, 1979, 37, 315.
- 36 Chen, Q.-Y.. Chin. J. Org. Chem., 2001, 21, 805.
- 37 Liu, J.; Wei, Q.; Huang, W.-Y., ZL 03115153.1, 2005.
- 38 Hubert, B.; Franck, G.; Zohra, B., US 2008015255A1, 2008.
- 39 Taylor, C. K.; Michalczyk, M. J.; Acosta, E. J., US 2009042996A1, 2009.
- 40 Christian, S. R.; Gordon, L. T.. J. Org. Chem., 1977, 42, 2680.
Governments Unite to Step-up Reduction on Global DDT Reliance and Add Nine New Chemicals under Internationaltreaty, Stockholm Convention Secretariat, Geneva, 8 May, 2008.
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