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HIGHLY EFFICIENT DEHYDROGENATION OF SECONDARY ALCOHOLS CATALYZED
2019
Acetophenone (IVa) [29]. 400 MHz, δ, ppm: 7.97–
7.95 m (2H), 7.58–7.54 m (1H), 7.48–7.44 m (2H),
2.61 s (3H).
1-(2-Chlorophenyl)ethanone (IVp) [32]. 400 MHz,
δ, ppm: 7.56–7.53 m (1H), 7.41–7.30 m (3 H), 2.64 s
(3H).
1-(p-Tolyl)ethanone (IVb) [29]. 400 MHz, δ, ppm:
7.85 d (J = 8 Hz, 2H), 7.25 d (J = 8 Hz, 2H), 2.57 s
(3H), 2.41 s (3H).
1-(Furan-2-yl)ethanone (IVq) [32]. 500 MHz, δ,
ppm: 7.58–7.59 d (J = 0.8, 1H), 7.18–7.19 d (J = 3.4,
1H), 6.53–6.54 d.d (J = 3.5, 1.6, 1H), 2.49 s (3H).
1-(4-Methoxyphenyl)ethanone (IVc) [29]. 400 MHz,
δ, ppm: 7.93 d (J = 8.8 Hz, 2H), 6.92 d (J = 8.8 Hz,
2H), 3.86 s (3H), 2.54 s (3H).
1-(Thiophen-2-yl)ethanone (IVr) [32]. 300 MHz,
δ, ppm: 7.69–7.70 d (J = 3.6, 1H), 7.63–7.64 d (J =
4.2, 1H), 7.11–7.14 t (J = 4.2, 1H), 2.57 s (3H).
1-(4-Chlorophenyl)ethanone (IVd) [29]. 400 MHz,
δ, ppm: 7.88 d (J = 8.8 Hz, 2H), 7.42 d (J = 8.8 Hz,
2H), 2.58 s (3H).
1-(Pyridin-2-yl)ethanone (IVs) [32]. 400 MHz, δ,
ppm: 8.68–8.67 m (1H), 8.04–8.02 m (1H), 7.84–7.80
m (1H), 7.48–7.45 m (1H), 2.72 s (3H).
1-(4-Bromophenyl)ethanone (IVe) [30]. (270 MHz)
δ 7.65 d (J = 9 Hz, 2H), 7.42 d (J = 8 Hz, 2H), 2.43 s
(3H).
Benzophenone (IVt) [31]. 400 MHz, δ, ppm: 7.81–
7.79 m (4H), 7.61–7.57 m (2H), 7.50–7.46 m (4H).
CONCLUSIONS
1-(4-Fluorophenyl)ethanone (IVf) [30]. 400 MHz,
δ, ppm: 8.00–7.96 m (2H), 7.15–7.11 m (2H), 2.58 s
(3H).
In conclusion, a new highly practical method is
presented for dehydrogenation of secondary alcohols
to the corresponding ketones by means of the iridium–
CNP complexes as catalysts. All secondary alcohols
were converted into the corresponding carbonyl
compounds in high isolated yields under a nitrogen
atmosphere. The reactions are compatible with
substrates bearing diverse functional groups and the
substitution patterns of alcohols have little influence
on the formation of the desired products.
1-(4-Nitrophenyl)ethanone (IVg) [30]. 400 MHz,
δ, ppm: 8.33–8.30 m (2H), 8.13–8.10 m (2H), 2.68 s
(3H).
1-[4-(trifluoromethyl)phenyl]ethanone (IVh)
[31]. 400 MHz, δ, ppm: 8.09 d (2HJ = 8.0 Hz), 7.74 d
(2H, J = 8.0 Hz), 2.65 s (2H).
1-(m-Tolyl)ethanone (IVi) [31]. 270 MHz, δ, ppm:
7.74–7.28 m (4H), 2.55 s (3H), 2.38 s (3H).
ACKNOWLEDGMENTS
1-(3-Methoxyphenyl)ethanone (IVj) [29].
(300 MHz), δ, ppm: 7.1–7.6 m (4H), 3.9 s (3H), 2.6 s
(3H).
We gratefully acknowledge financial support of this
work by the National Natural Science Foundation of
China (no. 21371080), the Natural Science Foundation
of Jiangsu Province (BK20130125), 333 Talent Project
of Jiangsu Province (BRA2012165).
1-(3-Chlorophenyl)ethanone (IVk) [30]. 400 MHz,
δ, ppm: 7.93–7.92 m (1H), 7.84–7.82 m (1H), 7.55–
7.52 m (1H), 7.43–7.39 m (1H), 2.59 s (3H).
1-(3-Bromophenyl)ethanone (IVl) [31]. 400 MHz,
δ, ppm: 8.20 m (1H), 7.99 d (1H, J = 8.21 Hz), 7.87 d
(1H, J = 8.20 Hz), 7.50 m (1H), 2.68 s (3H).
REFERENCES
1. Choi, J.H., Kim, N., Shin, Y.J., Park, J.H., and Park, J.,
Tetrahedron Lett., 2004, vol. 45, p. 4607.
1-(3-Nitrophenyl)ethanone (IVm) [31]. 400 MHz,
δ, ppm: 8.77 d (J = 2.0 Hz, 1H), 8.44–8.41 m (1H),
8.30–8.28 m (1H), 7.71–7.67 m (1H), 2.69 s (3H).
2. Meijer, R.H., Ligthart, G., Meuldijk, J., Vekemans, J.,
Hulshof, L.A., Mills, A.M., Kooijman, H., and Spek, A.L.,
Tetrahedron,2004, vol. 60, p. 1065.
1-(o-Tolyl)ethanone (IVn) [30]. 270 MHz, δ, ppm:
7.67–7.18 m (4H), 2.53 s (3H), 2.51 s (3H).
3. Keresszegi, C., Ferri, D., Mallat, T., and Baiker, A.,
J. Catal., 2005, vol. 234, p. 6475.
1-(2-Methoxyphenyl)ethanone (IVo) [31]. 400 MHz,
δ, ppm: 7.78 d (1H, J = 6.90 Hz), 7.70 m (1H), 7.26 d
(1H, J = 7.77 Hz), 7.17 m (1H), 3.99 s (3H), 2.71 s
(3H).
4. Rendler, S., Auer, G., and Oestreich, M., Angew. Chem.
Int. Ed., 2005, vol. 44, p.7620.
5. Zaccheria, F., Ravasio, N., Psaro, R., and Fusi, A.,
Chem. Commun., 2005, p. 253.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 10 2014