1666
BOYARSKII
metallics, 2015, vol. 34, p. 4515. doi 10.1021/
acs.organomet.5b00516
1,3-Dimethyl-2-(phenylethynyl)benzene (4d). Yield
148 mg (72%), light yellow oily material. H NMR
1
11. Mikhaylov, V.N., Sorokoumov, V.N., Korvinson, K.A.,
Novikov, A.S., and Balova, I.A., Organometallics, 2016,
vol. 35, no. 11, p. 1684. doi 10.1021/acs.organomet.6b00144
12. Anisimova, T.B., Guedes da Silva, M.F.C., Kukush-
kin, V.Yu., Pombeiro, A.J.L., and Luzyanin, K.V.,
Dalton Trans., 2014, vol. 43, p. 15861. doi 10.1039/
C4DT01917B
13. Luzyanin, K.V., Tskhovrebov, A.G., Carias, M.C.,
Guedes da Silva, M.F.C., Pombeiro, A.J.L., and Kukush-
kin, V.Y., Organometallics, 2009, vol. 28, p. 6559. doi
10.1021/om900682v
spectrum, δ, ppm: 2.58 s (6H, CH3), 7.11–7.18 m (3H),
7.39–7.41 m (3H), 7.59–7.61 m (2H).
4-(Phenylethynyl)aniline (4e). Yield 120 mg (62%).
1H NMR spectrum, δ, ppm: 3.89 br.s (2H, NH2), 6.66 d
(2H, J = 8.5 Hz), 7.33–7.37 m (5H), 7.53 d (2H, J =
9.5 Hz).
2-(Phenylethynyl)aniline (4f). Yield 58 mg (33%),
1
colorless solid, mp 87°C. H NMR spectrum, δ, ppm:
4.30 br.s (2H, NH2), 6.76 d (1H, J = 8.0 Hz), 7.15–7.19
m (1H), 7.34–7.40 m (5H), 7.55–7.57 m (2H).
14. Kinzhalov, M.A., Luzyanin, K.V., Boyarskiy, V.P.,
Haukka, M., and Kukushkin, V.Y., Organometallics
,
1,3,5-Trichloro-2-(phenylethynyl)benzene (4g). Yield
211 mg (75%), colorless solid, mp 120°C. 1H NMR spec-
trum, δ, ppm: 7.40–7.42 m (5H), 7.62–7.64 m (2H).
2013, vol. 32, p. 5212. doi 10.1021/om4007592
15. Miltsov, S.A., Karavan, V.S., Boyarsky, V.P., Gómez-de
Pedro, S., Alonso-Chamarro, J., and Puyol, M.,
Tetrahedron Lett., 2013, vol. 54, p. 1202. doi 10.1016/
j.tetlet.2012.12.060
ACKNOWLEDGMENTS
16. Kras’ko, S.A., Zlotskii, S.S., and Boyarskii, V.P., Russ.
J. Gen. Chem., 2015, vol. 85, no. 11, p. 2541. doi
10.1134/S1070363215110079
17. Khaibulova, T.Sh., Boyarskaya, I.A., and Boyarskii, V.P.,
Russ. J. Org. Chem., 2013, vol. 49, no. 3, p. 360. doi
10.1134/S1070428013030081
18. Ryabukhin, D.S., Sorokoumov, V.N., Savicheva, E.A.,
Boyarskiy, V.P., Balova, I.A., and Vasilyev, A.V.,
Tetrahedron Lett., 2013, vol. 54, p. 2369. doi 10.1016/
j.tetlet.2013.02.086
19. Savicheva, E.A., Kurandina, D.V., Nikiforov, V.A., and
Boyarskiy, V.P., Tetrahedron Lett., 2014, vol. 55,
p. 2101. doi 10.1016/j.tetlet. 2014.02.044
Synthesis of the palladium isocyanide complex was
performed under financial support by the Russian
Science Foundation (project no. 14-43-00017-P) using
the facilities of the Magnetic Resonance Research
Center and Chemistry Educational Center at the St.
Petersburg State University. Determination of catalytic
activity was funded by the St. Petersburg State
University (project no. 12.37.214.2016).
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