[1] (a) Pattison, G. Eur. J. Org. Chem. 2018, 2018, 3520;
(b) O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308;
(c) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320;
(d) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315.
[2] (a) Béguè, J.-P.; Bonnet-Delpon, D. Inhibition of Enzymes by Fluorinated Compounds. Bioorganic and Medicinal Chemistry of Fluorine, Wiley, Hoboken, NJ, 2008; Chapter 7, p. 246;
(b) Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology, Wiley & Sons, Chichester, 2009;
(c) Imperiali, B.; Abeles, R. H. Biochemistry 1986, 25, 3760;
(d) Sham, H. L.; Wideburg, N. E.; Spanton, S. G.; Kohlbrenner, W. E.; Betebenner, D. A.; Kempf, D. J.; Norbeck, D. W.; Plattner, J. J.; Erickson, J. W. J. Chem. Soc., Chem. Commun. 1991, 110;
(e) Giovani, S.; Penzo, M.; Brogi, S.; Brindisi, M.; Gemma, S.; Novellino, E.; Savini, L.; Blackman, M. J.; Campiani, G.; Butini, S. Bioorg. Med. Chem. Lett. 2014, 24, 3582.
[3] (a) Han, C.; Salyer, A. E.; Kim, E. H.; Jiang, X.; Jarrard, R. E.; Powers, M. S.; Kirchhoff, A. M.; Salvador, T. K.; Chester, J. A.; Hockerman, G. H.; Colby, D. A. J. Med. Chem. 2013, 56, 2456;
(b) Fah, C.; Hardegger, L. A.; Baitsch, L.; Schweizer, W. B.; Meyer, S.; Bur, D.; Diederich, F. Org. Biomol. Chem. 2009, 7, 3947;
(c) Fah, C.; Hardegger, L. A.; Ebert, M.-O.; Schweizer, W. B.; Diederich, F. Chem. Commun. 2010, 46, 67.
[4] The direct fluorination methods:(a) Verniest, G.; Van Hende, E.; Surmont, R.; De Kimpe, N. Org. Lett. 2006, 8, 4767;
(b) Iacono, C. E.; Stephens, T. C.; Rajan, T. S.; Pattison, G. J. Am. Chem. Soc. 2018, 140, 2036;
(c) Zupan, M.; Iskra, J.; Stavber, S. J. Org. Chem. 1995, 60, 259;
(d) Ramírez, J.; Fernández, E. Tetrahedron Lett. 2007, 48, 3841.
[5] Strategies based on already difluorinated building blocks:(a) Honraedt, A.; Van Der Lee, A.; Campagne, J. M.; Leclerc, E. Adv. Synth. Catal. 2017, 359, 2815;
(b) Arimitsu, S.; Fernandez, B.; del Pozo, C.; Fustero, S.; Hammond, G. B. J. Org. Chem. 2008, 73, 2656;
(c) Guo, C.; Wang, R.-W.; Qing, F.-L. J. Fluorine Chem. 2012, 143, 135;
(d) Ge, S.; Chaladaj, W.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 4149;
(e) Cao, C. R.; Jiang, M.; Liu, J. T. Eur. J. Org. Chem. 2015, 2015, 1144;
(f) Xiao, Y. L.; Guo, W. H.; He, G. Z.; Pan, Q.; Zhang, X. Angew. Chem., Int. Ed. 2014, 53, 9909;
(g) Zhao, H. Y.; Feng, Z.; Luo, Z.; Zhang, X. Angew. Chem., Int. Ed. 2016, 55, 10401;
(h) Qu, C.; Xu, P.; Ma, W.; Cheng, Y.; Zhu, C. Chem. Commun. 2015, 51, 13508;
(i) Adouama, C.; Keyrouz, R.; Pilet, G.; Monnereau, C.; Gueyrard, D.; Noel, T.; Medebielle, M. Chem. Commun. 2017, 53, 5653;
(j) Yu, J. S.; Liu, Y. L.; Tang, J.; Wang, X.; Zhou, J. Angew. Chem., Int. Ed. 2014, 53, 9512;
(k) Han, C.; Kim, E. H.; Colby, D. A. J. Am. Chem. Soc. 2011, 133, 5802;
(l) Yang, M. H.; Orsi, D. L.; Altman, R. A. Angew. Chem., Int. Ed. 2015, 54, 2361.
[6] (a) Ni, C.; Hu, J. Synthesis 2014, 46, 842;
(b) Hu, J.; Zhang, W.; Wang, F. Chem. Commun. 2009, 7465;
(c) Pan, X.-Y.; Zhao, Y.; Qu, H.-A.; Lin, J-H.; Hang, X.-C.; Xiao, J.-C. Org. Chem. Front. 2018, 5, 1452;
(d) Zhang, Z.; Yu, W.; Zhou, Q.; Li, T.; Zhang, Y.; Wang, J. Chin. J. Chem. 2016, 34, 473.
[7] (a) Kosobokov, M. D.; Dilman, A. D.; Levin, V. V.; Struchkova, M. I. J. Org. Chem. 2012, 77, 5850;
(b) Dilman, A. D.; Levin, V. V. Acc. Chem. Res. 2018, 51, 1272.
[8] (a) Wang, F.; Zhang, W.; Zhu, J.; Li, H.; Huang, K.; Hu, J. Chem. Commun. 2011, 47, 2411;
(b) Li, L.; Wang, F.; Ni, C.; Hu, J. Angew. Chem., Int. Ed. 2013, 52, 12390;
(c) Wang, W.; Yu, Q.; Zhang, Q.; Li, J.; Hui, F.; Yang, J.; Lv, J. Chin. J. Org. Chem. 2018, 38, 1569. (王为强, 余秦伟, 张前, 李江伟, 惠丰, 杨建明, 吕剑, 有机化学, 2018, 38, 1569.);
(d) Deng, X., Lin, J.; Zheng, J.; Xiao, J. Chin. J. Chem. 2014, 32, 689.
[9] (a) Xie, Q.; Ni, C.; Zhang, R.; Li, L.; Rong, J.; Hu, J. Angew. Chem., Int. Ed. 2017, 56, 1;
(b) Hu, M.; Ni, C.; Li, L.; Han, Y.; Hu, J. J. Am. Chem. Soc. 2015, 137, 14496.
[10] Zhang, Z.; Yu, W.; Wu, C.; Wang, C.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2015, 54, 1.
[11] (a) Levin, V. V.; Smirnov, V. O.; Struchkova, M. I.; Dilman, A. D. J. Org. Chem. 2015, 80, 9349;
(b) Tsymbal, A. V.; Kosobokov, M. D.; Levin, V. V.; Struchkova, M. I.; Dilman, A. D. J. Org. Chem. 2014, 79, 7831;
(c) Zemtsov, A. A.; Kondratyev, N, S.; Levin, V. V.; Struchkova, M. I.; Dilman, A. D. J. Org. Chem. 2014, 79, 818;
(d) Smirnov, V. O.; Struchkova, M. I.; Arkhipov, D. E.; Korlyukov, A. A.; Dilman, A. D. J. Org. Chem. 2014, 79, 11819;
(e) Levin, V. V.; Zemtsov, A. A.; Struchkova, M. I.; Dilman, A. D. Org. Lett. 2013, 15, 917;
(f) Kosobokov, M. D.; Levin, V. V.; Struchkova, M. I.; Dilman, A. D. Org. Lett. 2014, 16, 3784;
(g) Kosobokov, M. D.; Levin, V. V.; Struchkova, M. I.; Dilman, A. D. Org. Lett. 2015, 17, 760;
(h) Fedorov, O. V.; Kosobokov, M. D.; Levin, V. V.; Struchkova, M. I.; Dilman, A. D. J. Org. Chem. 2015, 80, 5870;
(i) Trifonov, A. L.; Zemtsov, A. A.; Levin, V. V.; Struchkova, M. I.; Dilman, A. D. Org. Lett. 2016, 18, 3458;
(j) Trifonov, A. L.; Levin, V. V.; Struchkova, M. I.; Dilman, A. D. Org. Lett. 2017, 19, 5304;
(k) Supranovich, V. I.; Levin, V. V.; Struchkova, M. I.; Korlyukov, A. A.; Dilman, A. D. Org. Lett. 2017, 19, 3215.
[12] (a) Song, X.; Chang, J.; Zhu, D.; Li, J.; Xu, C.; Liu, Q.; Wang, M. Org. Lett. 2015, 17, 1712;
(b) Chang, J.; Song, X.; Huang, W.; Zhu, D.; Wang, M. Chem. Commun. 2015, 51, 15362;
(c) Chang, J.; Xu, C.; Gao, J.; Gao, F.; Zhu, D.; Wang, M. Org. Lett. 2017, 19, 1850;
(d) Song, X.; Tian, S.; Zhao, Z.; Zhu, D.; Wang, M. Org. Lett. 2016, 18, 3414. |