Abstract
UV spectroscopic studies combined with kinetic measurements for the Suzuki–Miyaura reaction catalyzed by “ligand-free” catalytic systems have demonstrated that the base is involved in the formation of the palladium complexes ensuring the occurrence of the transmetalation stage. It follows from UV monitoring data for the catalytic reaction involving aryl iodides that a considerable part of palladium during the process is in the form of Pd2+ acid complexes with endogenous anions and does not participate in the main catalytic cycle.
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Miyaura, N., Yanagi, T., and Suzuki, A., Synth. Commun., 1981, vol. 11, no. 7, p. 513.
Seechurn, C.C.C., Kitching, M.O., Colacot, T.J., and Snieckus, V., Angew. Chem., Int. Ed. Engl., 2012, vol. 51, no. 21, p. 5062.
Suzuki, A., Angew. Chem., Int. Ed. Engl., 2011, vol. 50, no. 30, p. 6723.
Suzuki, A., J. Organomet. Chem., 1999, vol. 576, nos. 1–2, p. 147.
Cross Coupling Reactions: A Practical Guide, Miyaura, N., Berlin: Springer, 2002.
Miyaura, N., J. Organomet. Chem., 2002, vol. 653, nos. 1–2, p. 54.
Nunes, C.M. and Monteiro, A.L., J. Braz. Chem. Soc., 2007, vol. 18, no. 7, p. 1443.
Soomro, S.S., Ansari, F.L., Chatziapostolou, K., and Köhler, K., J. Catal., 2010, vol. 273, no. 2, p. 138.
Amatore, C., Came, E., Jutand, A., M’Barki, M.A., and Meyer, G., Organometallics, 1995, vol. 14, no. 12, p. 5605.
Matos, K. and Soderquist, J.A., J. Org. Chem., 1998, vol. 63, no. 3, p. 461.
Amatore, C., Jutand, A., and Le Duc, G., Chem. Eur. J., 2011, vol. 17, no. 8, p. 2492.
Carrow, B.P. and Hartwig, J.F., J. Am. Chem. Soc., 2011, vol. 133, no. 7, p. 2116.
Amatore, C., Le Duc, G., and Jutand, A., Chem. Eur. J., 2013, vol. 19, no. 31, p. 10082.
Amatore, C., Jutand, A., and Le Duc, G., Angew. Chem., Int. Ed. Engl., 2012, vol. 51, no. 6, p. 1379.
Butters, M., Harvey, J.N., Jover, J., Lennox, A.J.J., Lloyd-Jones, G.C., and Murray, P.M., Angew. Chem., Int. Ed. Engl., 2010, vol. 49, no. 30, p. 5156.
Crociani, B., Antonaroli, S., Marini, A., and Scrivanti, A., Dalton Trans., 2006, no. 24, p. 2698.
Braga, A.A.C., Morgon, N.H., Ujaque, G., and Maseras, F., J. Am. Chem. Soc., 2005, vol. 127, no. 27, p. 9298.
Braga, A.A.C., Morgon, N.H., Ujaque, G., Liedos, A., and Maseras, F., J. Organomet. Chem., 2006, vol. 691, no. 21, p. 4459.
Lima, C.F.R.A.C., Rodrigues, A.S.M.C., Silva, V.L.M., Silva, A.M.S., and Santos, L.M.N.B.F., ChemCatChem, 2014, vol. 6, no. 5, p. 1291.
Schmidt, A.F., Kurokhtina, A.A., and Larina, E.V., Catal. Sci. Technol., 2014, vol. 4, no. 10, p. 3439.
Schmidt, A.F., Kurokhtina, A.A., and Larina, E.V., Russ. J. Gen. Chem., 2011, vol. 81, no. 7, p. 1573.
Li, J.-H. and Liu, W.-J., Org. Lett., 2004, vol. 6, no. 16, p. 2809.
Zhang, Z. and Wang, Z., J. Org. Chem., 2006, vol. 71, no. 19, p. 7485.
Zhang, M. and Zhang, W., J. Phys. Chem. 2008, vol. 112, no. 16, p. 5245.
Kashin, A.N., Ganina, O.G., Cheprakov, A.V., and Beletskaya, I.P., ChemCatChem, 2015, vol. 7, no. 14, p. 2113.
Corbet, J.-P. and Mignani, G., Chem. Rev., 2006, vol. 106, no. 7, p. 2651.
Shmidt, A.F., Mametova, L.V., Dmitrieva, T.V., Shmidt, E.Y., and Tkach, V.S., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, vol. 40, no. 1, p. 190.
Shmidt, A.F., Al’-Khalaika, A., Smirnov, V.V., and Kurokhtina, A.A., Kinet. Catal., 2008, vol. 49, no. 5, p. 638.
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Original Russian Text © A.A. Kurokhtina, E.V. Larina, E.V. Yarosh, A.F. Schmidt, 2016, published in Kinetika i Kataliz, 2016, Vol. 57, No. 3, pp. 376–382.
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Kurokhtina, A.A., Larina, E.V., Yarosh, E.V. et al. Role of the base and endogenous anions in “ligand-free” catalytic systems for the Suzuki–Miyaura reaction. Kinet Catal 57, 373–379 (2016). https://doi.org/10.1134/S0023158416030095
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DOI: https://doi.org/10.1134/S0023158416030095