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Isotope Effect in Catalytic Hydroallylation of Norbornadiene by Allyl Formate

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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.

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REFERENCES

  1. Moiseev, I.I., Fedorovskaya, E.A., and Syrkin, Ya.K., Zh. Neorg. Khim., 1959, vol. 4, p. 2641.

    CAS  Google Scholar 

  2. 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.

    Book  Google Scholar 

  3. 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.

    Book  Google Scholar 

  4. Flid, V.R., Manulik, O.S., Belov, A.P., and Grigor’ev, A.A., Metalloorg. Khim., 1991, vol. 4, p. 864.

    CAS  Google Scholar 

  5. Flid, V.R., Gringolts, M.L., Shamsiev, R.S., Finkelshtein, E.Sh., Russ. Chem. Rev., 2018, vol. 87, p. 1169.

    Article  CAS  Google Scholar 

  6. Dzhemilev, U.M., Khusnutdinov, R.I., and Tolstikov, G.A., Usp. Khim., 1987, vol. 56, p. 65.

    Article  CAS  Google Scholar 

  7. Efros, I.E., Evstigneeva, E.M., Kolesnikova, A.A., and Flid, V.R., Ross. Khim. Zh., 2007, vol. 51, p. 103.

    Google Scholar 

  8. Tsukada, N., Sato, T., and Inoue, Y., Tetrahedron Lett., 2000, no. 41, p. 4181.

  9. Evstigneeva, E.M., Manulik, O.S., and Flid, V.R., Kinet. Catal., 2004, vol. 45, p. 172.

    Article  CAS  Google Scholar 

  10. Evstigneeva, E.M. and Flid, V.R., Russ. Chem. Bull., 2008, vol. 57, p. 837.

    Article  CAS  Google Scholar 

  11. Shamsiev, R.S. and Flid, V.R., Russ. Chem. Bull., 2013, vol. 62, p. 2301.

    Article  CAS  Google Scholar 

  12. 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.

    Article  Google Scholar 

  13. 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.

    Article  CAS  Google Scholar 

  14. Shamsiev, R.S., Tkhien, K.N., and Flid, V.R., Russ. Chem. Bull., 2013, vol. 62, p. 1553.

    Article  CAS  Google Scholar 

  15. Flid, V.R., Durakov, S.A., and Morozova, T.A., Russ. Chem. Bull., 2016, vol. 65, p. 2639.

    Article  CAS  Google Scholar 

  16. Durakov, S.A., Shamsiev, R.S., Flid, V.R., and Gekhman, A.E., Russ. Chem. Bull., 2018, vol. 67, p. 2234.

    Article  CAS  Google Scholar 

  17. Flid, V.R. and Durakov, S.A., Russ. Chem. Bull., 2018, vol. 67, p. 469.

    Article  CAS  Google Scholar 

  18. Chen, Y., Romarie, J.P., and Newhouse, T.R., J. Am. Chem. Soc., 2015, vol. 137, p. 5875.

    Article  CAS  PubMed  Google Scholar 

  19. Stolyarov, I.P., Demina, L.I., and Cherkashina, N.V., Russ. J. Inorg. Chem., 2011, vol. 56, p. 1532.

    Article  CAS  Google Scholar 

  20. 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.

  21. Flid, V.R., Durakov S.A., Morozova, T.A., Cheshkov, D.A., and Katsman, E.A., Russ. Chem. Bull., 2018, vol. 67, p. 1335.

    Article  CAS  Google Scholar 

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Correspondence to V. R. Flid.

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Dedicated to Academician of the Russian Academy of Sciences Ilya Iosifovich Moiseev in connection with his jubilee

Translated by Andrey Zeigarnik

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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

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  • DOI: https://doi.org/10.1134/S0023158419030042

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