Abstract
Norbornadiene allylation by allyl formate in the presence of palladium catalytic systems has a number of features associated with different directions of β-hydride transfer in key intermediates, which can be carried out with the participation of allyl, norbornenyl, or formyl fragments. The value of the kinetic isotope effect and the nature of the limiting step in the reaction of hydroallylation of norbornadiene are determined using deuterated reagents.
Similar content being viewed by others
REFERENCES
Moiseev, I.I., Fedorovskaya, E.A., and Syrkin, Ya.K., Zh. Neorg. Khim., 1959, vol. 4, p. 2641.
Cornils, B., Herrmann, W.A., Muhler, M., and Wong, C., Catalysis from A to Z: A Concise Encyclopedia, 4 Volume set Completely Revised and Enlarged Edition, New York: Wiley, 2013, p. 79.
Cornils, B., Herrmann, W.A., Beller, M., and Paciello, R., Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Four Volumes, New York: Wiley, 2017, 3rd ed., p. 1366.
Flid, V.R., Manulik, O.S., Belov, A.P., and Grigor’ev, A.A., Metalloorg. Khim., 1991, vol. 4, p. 864.
Flid, V.R., Gringolts, M.L., Shamsiev, R.S., Finkelshtein, E.Sh., Russ. Chem. Rev., 2018, vol. 87, p. 1169.
Dzhemilev, U.M., Khusnutdinov, R.I., and Tolstikov, G.A., Usp. Khim., 1987, vol. 56, p. 65.
Efros, I.E., Evstigneeva, E.M., Kolesnikova, A.A., and Flid, V.R., Ross. Khim. Zh., 2007, vol. 51, p. 103.
Tsukada, N., Sato, T., and Inoue, Y., Tetrahedron Lett., 2000, no. 41, p. 4181.
Evstigneeva, E.M., Manulik, O.S., and Flid, V.R., Kinet. Catal., 2004, vol. 45, p. 172.
Evstigneeva, E.M. and Flid, V.R., Russ. Chem. Bull., 2008, vol. 57, p. 837.
Shamsiev, R.S. and Flid, V.R., Russ. Chem. Bull., 2013, vol. 62, p. 2301.
Evstigneeva, E.M., Manulik, O.S., Flid, V.R., Stolyarov, I.P., Kozitsyna, N.Yu., Vargaftik, M.N., and Moiseev, I.I., Russ. Chem. Bull., 2004, vol. 53, p. 1348.
Stolyarov, I.P., Gekhman, A.E., Moiseev, I.I., Kolesnikov, A.Yu., Evstigneeva, E.M., and Flid, V.R., Russ. Chem. Bull., 2007, vol. 56, p. 320.
Shamsiev, R.S., Tkhien, K.N., and Flid, V.R., Russ. Chem. Bull., 2013, vol. 62, p. 1553.
Flid, V.R., Durakov, S.A., and Morozova, T.A., Russ. Chem. Bull., 2016, vol. 65, p. 2639.
Durakov, S.A., Shamsiev, R.S., Flid, V.R., and Gekhman, A.E., Russ. Chem. Bull., 2018, vol. 67, p. 2234.
Flid, V.R. and Durakov, S.A., Russ. Chem. Bull., 2018, vol. 67, p. 469.
Chen, Y., Romarie, J.P., and Newhouse, T.R., J. Am. Chem. Soc., 2015, vol. 137, p. 5875.
Stolyarov, I.P., Demina, L.I., and Cherkashina, N.V., Russ. J. Inorg. Chem., 2011, vol. 56, p. 1532.
Al' Khazradzhi, A.Kh., Krylov, A.V., Kulikova, M.V., Flid, V.R., and Tkachenko, O.Yu., Tonkie Khim. Tekhnol., 2016, vol. 11, no. 6, p. 70.
Flid, V.R., Durakov S.A., Morozova, T.A., Cheshkov, D.A., and Katsman, E.A., Russ. Chem. Bull., 2018, vol. 67, p. 1335.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician of the Russian Academy of Sciences Ilya Iosifovich Moiseev in connection with his jubilee
Translated by Andrey Zeigarnik
Rights and permissions
About this article
Cite this article
Durakov, S.A., Shamsiev, R.S., Flid, V.R. et al. Isotope Effect in Catalytic Hydroallylation of Norbornadiene by Allyl Formate. Kinet Catal 60, 245–249 (2019). https://doi.org/10.1134/S0023158419030042
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0023158419030042