[1] For recent reviews, see: (a) Smart, B. E. J. Fluorine Chem. 2001, 109, 3.(b) Maienfisch, P.; Hall, R. G. Chimia 2004, 58, 93.(c) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.(d) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.(e) Zhang J.; Jin C.; Zhang Y. Chin. J. Org. Chem. 2014, 34, 662 (in Chinese).(张霁, 金传飞, 张英俊, 有机化学, 2014, 34, 662.)
[2] For selected recent reviews of fluorination, see: (a) Grushin, V. V. Acc. Chem. Res. 2010, 43, 160.(b) Furuya, T.; Klein, J. E. M. N.; Ritter, T. Synthesis 2010, 1804.(c) Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470.(d) Campbell, M. G.; Ritter, T. Org. Process Res. Dev. 2014, 18, 474.(e) Li, Y.; Wu, Y.; Li, G.-S.; Wang, X.-S. Adv. Synth. Catal. 2014, 356, 1412.(f) Yang, X.; Wu, T.; Phipps, R. J.; Toste, F. D. Chem. Rev. 2015, 115, 826.
[3] For selected reviews of trifluoromethylation, see: (a) Ma, J.-A.; Cahard, D. Chem. Rev. 2004, 104, 6119.(b) Schlosser, M. Angew. Chem., Int. Ed. 2006, 45, 5432.(c) Ma, J.-A.; Cahard, D. J. Fluorine Chem. 2007, 128, 975.(d) Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470.(e) Prakash, G. K. S.; Mandal, M. J. Fluorine Chem. 2011, 112, 123.(f) Roy, S.; Gregg, B. T.; Gribble, G. W.; Le, V.-D.; Roy, S. Tetrahedron 2011, 67, 2161.(g) Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475.(h) Jin, Z.; Hammond, G. B.; Xu, B. Aldrichim. Acta 2012, 45, 67.(i) He, H.; Huang, Y.; Verpoort, F. Acta Chim. Sinica 2013, 71, 700 (in Chinese).(何展荣, 黄毅勇, Verpoort Francis, 化学学报, 2013, 71, 700.) (j) Wang, G.; He, X.; Dai, J.; Xu, H. Chin. J. Org. Chem. 2014, 34, 837 (in Chinese).(王光祖, 赫侠平, 戴建军, 许华建, 有机化学, 2014, 34, 837.)(k) Zhang, K.; Xu, X.; Qing, F. Chin. J. Org. Chem. 2015, 35, 556 (in Chinese).(张柯, 徐修华, 卿凤翎, 有机化学, 2015, 35, 556.)(l) Liu, X.; Xu, C.; Wang, M.; Liu, Q. Chem. Rev. 2015, 115, 683.
[4] For a review on a-trifluoromethylated carbanion synthons, see: Uneyama, K.; Katagiri, T.; Amii, H. Acc. Chem. Res. 2008, 41, 817, and references therein.
[5] (a) Ishikawa, N.; Yokozawa, T. Bull. Chem. Soc. Jpn. 1983, 56, 724.(b) Beck, D.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1986, 25, 98.(c) Fuchigami, T.; Nakagawa, Y. J. Org. Chem. 1987, 52, 5276.(d) Qian, C.-P.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 4602.(e) Beck, A. K.; Seebach, D. Chem. Ber. 1991, 124, 2897.(f) Yamaguchi, Y.; Kawate, T.; Itahashi, H.; Katagiri, T.; Uneyama, K. Tetrahedron Lett. 2003, 44, 6319.(g) Sato, K.; Takiguchi, Y.; Yoshizawa, Y.; Iwase, K.; Shimizu, Y.; Tarui, A.; Omote, M.; Kumadaki, I.; Ando, A. Chem. Pharm. Bull. 2007, 55, 1593.(h) Guo, Y.; Zhao, X.; Zhang, D.; Murahashi, S.-I. Angew. Chem., Int. Ed. 2009, 48, 2047.(i) Shibata, N.; Suzuki, S.; Furukawa, T.; Kawai, H.; Tokunaga, E.; Yuan, Z.; Cahard, D. Adv. Synth. Catal. 2011, 353, 2037.(j) Li, L.; Huang, D.; Chen, Q.-Y.; Guo, Y. Synlett 2013, 611.(k) Li, L.; Chen, Q.-Y.; Guo, Y. Chem. Commun. 2013, 49, 8764.(l) Wang, Q.; Huan, F.; Shen, H., Xiao, J.-C.; Gao, M.; Yang, X.; Murahashi, S.-I.; Chen, Q.-Y.; Guo, Y. J. Org. Chem. 2013, 78, 12525.
[6] For examples on asymmetric addition reactions of sulfonates, see: (a) Nishimura, T.; Takiguchi, Y.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 9086.(b) Lu, J.; Ye, J.; Duan, W.-L. Org. Lett. 2013, 15, 5016.(c) Lu, J.; Ye, J.; Duan, W.-L. Chem. Commun. 2014, 50, 698.
[7] For a review on the synthesis and application of sultones, see: Mondal, S. Chem. Rev. 2012, 112, 5339.
[8] CCDC 1427062 contain the supplementarycrystallographic data for this paper
[9] Preparation of hexafluoro-isopropyl α,β-alkenyl sulfonates bearing the β-alkyl moiety was unsuccessful. |