Michael Addition Reaction of Fluorinated Nitro Compounds
Feng Huan
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
College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China
Search for more papers by this authorCorresponding Author
Yangen Huang
College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China
Yangen Huang, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China, Tel.: 0086-021-67792612; Fax: 0086-021-6779260
Yong Guo, Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Tel.: 0086-021-54925462; Fax: 0086-021-64166128
Search for more papers by this authorQingyun Chen
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
Yong Guo
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Yangen Huang, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China, Tel.: 0086-021-67792612; Fax: 0086-021-6779260
Yong Guo, Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Tel.: 0086-021-54925462; Fax: 0086-021-64166128
Search for more papers by this authorFeng Huan
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
College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China
Search for more papers by this authorCorresponding Author
Yangen Huang
College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China
Yangen Huang, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China, Tel.: 0086-021-67792612; Fax: 0086-021-6779260
Yong Guo, Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Tel.: 0086-021-54925462; Fax: 0086-021-64166128
Search for more papers by this authorQingyun Chen
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
Yong Guo
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Yangen Huang, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China, Tel.: 0086-021-67792612; Fax: 0086-021-6779260
Yong Guo, Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Tel.: 0086-021-54925462; Fax: 0086-021-64166128
Search for more papers by this authorAbstract
The Michael addition reactions of fluorinated nitro compounds with electron deficient olefins to give γ-fluoro-γ-nitro-esters, nitriles and ketones which bear a fluorinated quaternary carbon center were reported. The reactions were promoted by TMG, affording the desired adducts in acceptable to good yields.
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REFERENCES
- 1 Xiao, W.. Chem. Commun., 2009, 4251.
- 2 For a review on nitro-Michael additions, see: Ballini, R.; Bosica, G.; Fiorini, D.; Palmieri, A.; Petrini, M.. Chem. Rev., 2005, 105, 933.
- 3
Ono, N.,
The Nitro Group in Organic Synthesis, Ed.: H. Feuer, Wiley-VCH, New York, 2001.
10.1002/0471224480 Google Scholar
- 4
Chambers, R. D., Fluorine in Organic Chemistry, Blackwell Publishing Ltd./CRC Press, Boca Raton, FL, 2004
10.1002/9781444305371 Google Scholar
- 5
Hiyama, T., Organofluorine Compounds, Chemistry and Applications, Springer-Verlag, Berlin, 2000.
10.1007/978-3-662-04164-2 Google Scholar
- 6
Kirsch, P., Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2004.
10.1002/352760393X Google Scholar
- 7
Soloshonok, V. A., Fluorine-Containing Synthons, ACS Symposium Series 911, Oxford University Press, Washington, DC, 2005.
10.1021/bk-2005-0911 Google Scholar
- 8
Uneyama, K., Organofluorine Chemistry, Blackwell Publishing, Oxford, 2006.
10.1002/9780470988589 Google Scholar
- 9 Muller, K.; Faeh, C.; Diederich, F.. Science, 2007, 317, 1881.
- 10
Schlosser, M..
Angew. Chem., Int. Ed.,
1998,
37,
1496.
10.1002/(SICI)1521-3773(19980619)37:11<1496::AID-ANIE1496>3.0.CO;2-U CAS PubMed Web of Science® Google Scholar
- 11 O'Hagan, D.. Chem. Soc. Rev., 2008, 37, 308.
- 12 Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V.. Chem. Soc. Rev., 2008, 37, 320.
- 13 Kirk, K. L.. Org. Proc. Res. Dev., 2008, 12, 305.
- 14 O'Hagan, D.. J. Fluorine Chem., 2010, 131, 1071.
- 15 Thayer, A. M.. Chem. Eng. News, 2006, 84, 15.
- 16 Ma, J.-A.; Cahard, D.. Chem. Rev., 2004, 104, 6119.
- 17a Davis, F. A.; Kasu, P. V. N.. Org. Prep. Proced. Int., 1999, 31, 125.
- 17b Cahard, D.; Xu, X.; Couve-Bonnaire, S.; Pannecoucke, X.. Chem. Soc. Rev., 2010, 39, 558.
- 17c Lectard, S.; Hamashima, Y.; Sodeoka, M.. Adv. Synth. Catal., 2010, 352, 2708.
- 17d Ma, J.-A.; Cahard, D.. Chem. Rev., 2008, 108, PR1.
- 17e Brunet, V. A.; O'Hagan, D.. Angew. Chem., Int. Ed., 2008, 47, 1179.
- 17f Shibata, N.; Ishimaru, T.; Nakamura, S.; Toru, T.. J. Fluorine Chem., 2007, 128, 469.
- 17g Prakash, G. K. S.; Beier, P.. Angew. Chem., Int. Ed., 2006, 45, 2172.
- 17h Pihko, P. M.. Angew. Chem., Int. Ed., 2006, 45, 544.
- 17i Bobbio, C.; Gouverneur, V.. Org. Biomol. Chem., 2006, 4, 2065.
- 17j Hamashima, Y.; Sodeoka, M.. Synlett, 2006, 1467.
- 17k Mikami, K.; Itoh, Y.; Yamanaka, M.. Chem. Rev., 2004, 104, 1.
- 18a Smith, A. M. R.; Hii, K. K.. Chem. Rev., 2011, 111, 1637.
- 18b Shibatomi, K.. Synthesis, 2010, 2679.
- 18c Bella, M.; Gasperi, T.. Synthesis, 2009, 1583.
- 18d Ueda, M.; Kano, T.; Maruoka, K.. Org. Biomol. Chem., 2009, 7, 2005.
- 18e Cozzi, P. G.; Hilgraf, R.; Zimmermann, N.. Eur. J. Org. Chem., 2007, 5969.
- 18f Marigo, M.; Jørgensen, K. A.. Chem. Commun., 2006, 2001.
- 18g Oestreich, M.. Angew. Chem., Int. Ed., 2005, 44, 2324.
- 18h France, S.; Weatherwax, A.; Lectka, T.. Eur. J. Org. Chem., 2005, 475.
- 18i Ibrahim, H.; Togni, A.. Chem. Commun., 2004, 1147.
- 19a Shibatomi, K.; Futatsugi, K.; Kobayashi, F.; Iwasa, S.; Yamamoto, H.. J. Am. Chem. Soc., 2010, 132, 5625.
- 19b Shibatomi, K.; Yamamoto, H.. Angew. Chem., Int. Ed., 2008, 47, 5796.
- 19c Arai, S.; Oku, M.; Ishida, T.; Shioiri, T.. Tetrahedron Lett., 1999, 40, 6785.
- 19d Nakamura, M.; Hajra, A.; Endo, K.; Nakamura, E.. Angew. Chem., Int. Ed., 2005, 44, 7248.
- 19e Burger, E. C.; Barron, B. R.; Tunge, J. A.. Synlett, 2006, 2824.
- 19f Bélanger, é.; Cantin, K.; Messe, O.; Tremblay, M.; Paquin, J.-F.. J. Am. Chem. Soc., 2007, 129, 1034.
- 19g Bélanger, é.; Houzé, C.; Guimond, N.; Cantin, K.; Paquin, J.-F.. Chem. Commun., 2008, 3251.
- 19h Bélanger, é.; Pouliot, M.-F.; Paquin, J.-F.. Org. Lett., 2009, 11, 2201.
- 19i Guo, Y.; Twamley, B.; Shreeve, J. M.. Org. Biomol. Chem., 2009, 7, 1716.
- 19j Guo, Y.; Tao, G.-H.; Blumenfeld, A.; Shreeve, J. M.. Organometallics, 2010, 29, 1818.
- 19k Shibatomi, K.; Narayama, A.; Soga, Y.; Muto, T.; Iwasa, S.. Org. Lett., 2011, 13, 2944.
- 19l Kang, S. H.; Kim, D. Y.. Adv. Synth. Catal., 2010, 352, 2783.
- 20 Hu, H.; Huang, Y.; Guo, Y.. J. Fluorine Chem., 2011, 133, 108.
- 21 Takeuchi, Y.; Nagata, K.; Koizumi, T.. J. Org. Chem., 1987, 52, 5061.