Perfluoroalkylation of coumarins
Russ. Chem. Bull., Int. Ed., Vol. 66, No. 8, August, 2017
1449
Found (%): C, 57.93; H, 3.02. C H F O . Calculated (%):
C, 57.90; H, 3.09. Physicochemical characteristics of comꢀ
plexes correspond to the literature data.38
17. M. Khrizanforov, T. Gryaznova, O. Sinyashin, Y. Budnikꢀ
ova, J. Organomet. Chem., 2012, 718, 101.
18. M. N. Khrizanforov, T. V. Gryaznova, D. Yu. Mikhailov,
Yu. H. Budnikova, O. G. Sinyashin, Russ. Chem. Bull., 2012,
61, 1560.
19. G. Landelle, A. Panossian, S. Pazenok, J. P. Vors, F. R.
Leroux, Beilstein J. Org. Chem., 2013, 9, 2476
20. T. V. Gryaznova, V. V. Khrizanforova, K. V. Kholin, M. N.
Khrizanforov, Yu. H. Budnikova, Russ. Chem. Bull., 2016,
65, 1798.
21. M. N. Khrizanforov, S. V. Fedorenko, S. O. Strekalova,
K. V. Kholin, A. R. Mustafina, M. Ye. Zhilkin, V. V. Khriꢀ
zanforova, Y. N. Osin, V. V. Salnikov, T. V. Gryaznova,
Y. H. Budnikova, Dalton Trans., 2016, 45, 11976.
22. D. Y. Mikhaylov, T. V. Gryaznova, Y. Dudkina, M. N.
Khrizanphorov, Sh. Latypov, O. Kataeva, D. A. Vicic, O. G.
Sinyashin, Yu. H. Budnikova, Dalton Trans., 2012, 41, 165.
23. Y. B. Dudkina, M. N. Khrizanforov, T. V. Gryaznova, Y. H.
Budnikova, J. Organomet. Chem., 2014, 751, 301.
24. Z. He, T. Luo, M. Hu, Y. Cao, J. Hu, Angew. Chem., Int.
Ed., 2012, 51, 3944.
1
1
8
3
2
7
ꢀMethylꢀ3ꢀ(perfluorohexyl)ꢀ2Hꢀchromenꢀ2ꢀone (8). White
1
crystals with a pink tint, m.p. 123—125 °C. H NMR (600 MHz,
CDСl ), δ: 8.34 (s, 1 H, H(4)); 7.74—7.20 (m, 3 H); 2.43 (s, 3 H).
С NMR (100.6 MHz, CDСl ), δ: 156.3, 154.8, 146.3, 143.2,
3
1
3
3
19
1
29.1, 126.5, 121.5, 117.2, 116.4, 114.4, 22.2. F NMR (376 MHz,
CDCl ), δ: –81.33 (t, 3 F, J = 9.8 Hz); –105.32 (t, 2 F,
3
J = 14.5 Hz); –120.19 (br.s, 2 F); –121.93 (br.s, 2 F); –122.47
–
l
(
1
br.s, 2 F); –126.05 (br.s, 2 F). IR, ν/cm : 3072, 1604, 1510,
+
462, 1195. MS, m/z: 478 [M] . Found (%): C, 40.17; H, 1.41.
C16H7F13O . Calculated (%): C, 40.19; H, 1.48.
2
7
ꢀMethylꢀ3ꢀ(trifluoromethyl)ꢀ2Hꢀchromenꢀ2ꢀone (9). White
1
crystals, m.p. 120—122 °C. H NMR (600 MHz, CDСl ), δ:
3
8
.11 (s, 1 H, C(4)H); 7.49 (d, 1 H, ArH, J = 8.0 Hz); 7.18 (d, 2 H,
1
3
ArH, J = 7.6 Hz); 2.5 (s, 3 H, C(7)Me). С NMR (100.6 MHz,
CDСl ), δ: 156.2, 154.8, 146.4, 143.2, 129.1, 126.5, 121.5,
1
3
1
9
17.5, 116.4, 114.4, 22.0. F NMR (376 МHz, CDCl ), δ:
3
+
–
65.5 (s, 3 F). MS, m/z: 229.05 [M] . Found (%): C, 57.95;
H, 3.00. C H F O . Calculated (%): C, 57.90; H, 3.09. Physiꢀ
1
1
8
3
2
cochemical characteristics of complexes correspond to the litꢀ
erature data.
25. K. Fujikawa, Y. Fujioka, A. Kobayashi, H. Amii, Org. Lett.,
2011, 13, 5560.
3
8
2
6. N. Iqbal, J. Jung, S. Park, E. J. Cho, Angew. Chem., 2014,
126, 549.
This work was financially supported by the Russian
Science Foundation (Project No. 14ꢀ23ꢀ00016).
27. E. J. Cho, T. D. Senecal, T. Kinzel, Y. Zhang, D. A. Watꢀ
son, S. L. Buchwald, Science, 2010, 328, 1679.
2
2
3
8. D. Yu, Z. Gang, H. Weiyuan, Tetrahedron Lett., 1993,
4, 1321.
9. Y. Wu, H. R. Zhang, R. X. Jin, Q. Lan, X. S. Wang, Adv.
Synth. Catal., 2016, 358, 3528.
0. M. Khrizanforov, S. Strekalova, V. Khrizanforova, V. Griꢀ
nenko, K. Kholin, M. Kadirov, T. Burganov, A. Gubaidulꢀ
lin, T. Gryaznova, O. Sinyashin, L. Xu, D. A. Vicic,
Y. Budnikova, Dalton Trans., 2015, 44, 19674.
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Received March 31, 2017;
in revised form July 10, 2017