Mendeleev Commun., 2017, 27, 139–140
3 (a) V. V. Levin, A. A. Zemtsov, M. I. Struchkova and A. D. Dilman, Org.
the reaction proceeds with moderate yield, it provides rapid
assembly of valuable organofluorine compounds from three
independently variable and readily available components.
Lett., 2013, 15, 917; (b) V. V. Levin, A. A. Zemtsov, M. I. Struchkova
and A. D. Dilman, J. Fluorine Chem., 2015, 171, 97.
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and A. D. Dilman, J. Org. Chem., 2014, 79, 11819; (b) S. S. Ashirbaev,
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(d) A. A. Zemtsov, A. D. Volodin, V. V. Levin, M. I. Struchkova and A. D.
Dilman, Beilstein J. Org. Chem., 2015, 11, 2145; (e) N. S. Kondratyev,
V. V. Levin,A.A. Zemtsov, M. I. Struchkova andA. D. Dilman, J. Fluorine
Chem., 2015, 176, 89.
This work was supported by the Russian Ministry of Education
and Science (grant no. MK-6724.2016.3) and the Russian Founda-
tion for Basic Research (project no. 14-03-00293). We are grateful
to A. Zemtsov and N. Kondratyev for performing preliminary
experiments.
5 (a) A. Yazici and S. G. Pyne, Synthesis, 2009, 339; (b) A. Yazici and
S. G. Pyne, Synthesis, 2009, 513; (c) A. Padwa and D. Bellus, in Science
of Synthesis, 27: Category 4. Compounds with Two Carbon Heteroatom
Bonds, Georg Thieme Verlag, Stuttgart, 2005.
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Online Supplementary Materials
Supplementary data associated with this article (experimental
procedures, product characterization, NMR spectra) can be found
in the online version at doi: 10.1016/j.mencom.2017.03.010.
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N-(2,2-Difluoro-1,3-diphenylpropyl)-N-methylpivalamide 5a. Yield
190 mg (55%). Colorless crystals, mp 100–101°C, Rf 0.32 (hexanes–
EtOAc, 8:1). 1H NMR (300 MHz, CDCl3) d: 1.35 (s, 9H), 3.02 (s, 3H),
3.08–3.39 (m, 2H), 6.51 (t, 1H, J 15.6 Hz), 7.20–7.58 (m, 10H). 13C NMR
(75 MHz, CDCl3) d: 28.3, 33.2 (t, J 3.4 Hz), 39.4, 41.9 (t, J 24.3 Hz),
59.3 (dd, J 27.0, 22.4 Hz), 123.9 (t, J 250.1 Hz), 127.5, 128.2, 128.4, 128.8,
129.9 (t, J 2.3 Hz), 132.3 (dd, J 4.0, 1.7 Hz), 134.5, 178.6. 19F NMR
(282 MHz, CDCl3) d: –102.1 (dm, 1F, J 250.1 Hz), –99.9 (dm, 1F,
J 250.1 Hz). HRMS (ESI), m/z: 346.1971 [M+H]+ (calc. for C21H26F2NO,
m/z: 346.1977).
For characteristics of products 5b–e, see Online Supplementary Materials.
Received: 3rd October 2016; Com. 16/5063
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