Abstract
The mechanisms of carbonylation of alkenes, alkynes, and alcohols, including the mechanism of oxidative carbonylation of alkynes in the regime of self-oscillations catalyzed by Pd(II), Pd(I), or Pd(0) complexes, are analyzed. It is shown that the main reasons for the appearance of self-oscillations in the oxidation reactions are nonlinear and autocatalytic steps of generation and termination of active centers. The results of studying the functions of para-benzoquinone as an oxidant, ligand, and catalyst in the oxidative reactions are generalized. It is found that Pd(0) complexes with para-benzoquinone can catalyze oxidation reactions.
Similar content being viewed by others
REFERENCES
Smidt, J., Hafner, W., Jira, R., Sedlmeier, J., Siber, R., Ruttinger, R., and Koier, H., Angew. Chem., 1959, vol. 71, p. 176.
Moiseev, I.I., p-Kompleksy v zhidkofaznom okislenii olefinov ?p-Complexes in the Liquid-Phase Alkene Oxidation), Moscow: Nauka, 1970.
Heck, R.F., Palladium Reagent in Organic Synthesis, London: Academic, 1985.
Herrmann, W.A., Applied Homogeneous Catalysis with Organometallic Compounds, Cornils, B. and Hermann, W.A., Eds., Weinheim: VCH, 1996. vol. VII, p. 712.
Maitlis, P.M., The Organometallic Chemistry of Palladium, New York: Academic, 1971, vols. 1, 2.
Henry, P.M., Palladium-Catalyzed Oxidation of Hydro-carbons, Dordrecht: Reidel, 1980.
Tsuji, J., Palladium Reagent, Innovation in Organic Synthesis, Chichester: Wiley, 1995.
Tsuji, J., Transition Metal Reagents and Catalysts, Chichester: Wiley, 2000.
Malleron, J.-L., Fiaud, J.C., and Legros, J.-Y., Hand-book of Palladium-Catalyzed Organic Reactions, New York: Academic, 1997.
Tsuji, J., Acc. Chem. Res., 1969, vol. 2, p. 144.
Forster, D., Hershman, A., and Morris, D.E., Cat. Rev. - Sci. Eng., 1981, vol. 23, p. 89.
Bardi, R., Del Pra, A., Piazzesi, A.M., and Toniolo, L., Inorg. Chim. Acta, 1979, vol. 35, p. 345.
Protchenko, A.V., Shifrina, R.R., and Petrov, E.S., Neftekhimiya, 1998, vol. 28, p. 200.
Cavinato, G. and Toniolo, L., J. Organomet. Chem., 1990, vol. 398, p. 187.
Noskov, Yu.G., Simonov, A.P., and Petrov, E.S., Kinet. Katal., 2000, vol. 41, no.4, p. 564.
Noskov, Yu.G., Novikov, N.A., Terekhova, M.I., and Petrov, E.S., Kinet. Katal., 1991, vol. 32, no.2, p. 331.
Petrova, N.E., Noskov, Yu.G., Terekhova, M.I., and Petrov, E.S., Zh. Obshch. Khim., 1993, vol. 63, p. 678.
Noskov, Yu.G., Terekhova, M.I., and Petrov, E.S., Kinet. Katal., 1993, vol. 34, no.6, p. 1001.
Noskov, Yu.G. and Petrov, E.S., Kinet. Katal., 1993, vol. 34, p. 1005.
Noskov, Yu.G. and Petrov, E.S., Kinet. Katal., 1994, vol. 35, no.5, p. 728.
Kron, T.E., Noskov, Yu.G., Terekhova, M.I., and Petrov, E.S., Zh. Fiz. Khim., 1996, vol. 70, p. 82.
Noskov, Yu.G. and Petrov, E.S., Kinet. Katal., 1997, vol. 38, no.4, p. 568.
Petrov, E.S. and Noskov, Yu.G., Ross. Khim. Zh., 1998, vol. 42, p. 149.
Noskov, Yu.G. and Petrov, E.S., Izv. Akad. Nauk, Ser. Khim., 2001, no. 10, p. 1756.
Estaham, G.R., Heaton, B.T., Iggo, J.A., Teoze, R.P., Whyman, R., and Zacchiny, S., J. Chem. Soc., Chem. Commun., 2000, p. 609.
Temkin, O.N., Kaliya, O.L., Flid, R.M., and Mekhryakova, N.G., Dokl. Akad. Nauk SSSR, 1971, vol. 199, p. 1321.
Heck, R.F., J. Am. Chem. Soc., 1972, vol. 94, p. 2712.
Temkin, O.N., Mekhryakova, N.G., Bruk, L.G., Kaliya, O.L., and Prudnikov, A.Yu., Kinet. Katal., 1979, vol. 20, p. 629.
Temkin, O.N., Zhir-Lebed', L.N., Mekhryakova, N.G., Flid, R.M., and Golodov, V.A., Kinet. Katal., 1974, vol. 15, p. 537.
James, D. and Stille, J., J. Am. Chem. Soc., 1976, vol. 98, p. 1810.
Zhir-Lebed', L.N., Mekhryakova, N.G., Golodov, V.A., and Temkin, O.N., Zh. Org. Khim., 1975, vol. 11, p. 2297.
Rivetty, F. and Romano, U., J. Organomet. Chem., 1978, vol. 154, p. 323.
Zhir-Lebed', L.N., Temkin, O.N., et al., Koord. Khim., 1978, vol. 4, p. 1046.
Del Piero, G. and Cesari, V., Acta Crystallogr., 1975, vol. 1335, p. 241.
Milstein, D. and Huckaby, J.L., J. Am. Chem. Soc., 1982, vol. 104, p. 6150.
Temkin, O.N. and Bruk, L.G., Usp. Khim., 1983, vol. 52, p. 206.
Moiseev, I.I., Itogi Nauki Tekh., Kinet. Katal., 1984, vol. 13, p. 147.
Vargaftik, M.N., Moiseev, I.I., Kochubey, D.I., and Zamaraev, K.I., J. Mol. Catal., 1989, vol. 53, p. 315.
Moiseev, I.I. and Vargaftik, M.N., Catalysis by Di-and Polynuclear Metal Complexes, Cotton, F.A. and Adams, R., Eds., London: Wiley-VCH, 1998, no. 4, p. 395.
Moiseev, I.I. and Vargaftik, M.N., Zh. Obshch. Khim., 2002, vol. 72, p. 550.
Catellani, M., Chiusoli, G.P., and Costa, M., Pure Appl. Chem., 1990, vol. 62, p. 623.
Brunel, J.M., Hirlemann, M.H., Heumann, A., and Buono, G., Chem. Commun, 2000, p. 1869.
Bruk, L.G. and Temkin, O.N., Inorg. Chim. Acta, 1998, vol. 280, p. 202.
Kulik, A.V., Bruk, L.G., Temkin, O.N., Khabibulin, V.R., Belsky, V.K., and Zavodnik, V.E., Mendeleev Commun., 2002, no. 1, p. 47.
Shulyakovskii, G.M., Temkin, O.N., Bykanova, N.V., and Nyrkova, A.N., Khimicheskaya kinetika v katalize: Kineticheskie modeli zhidkofaznykh reaktsii (Chemical Kinetics in Catalysis: Kinetic Model of Liquid-Phase Reactions) Chernogolovka: Inst. Chem. Phys., 1985, p. 112.
Malashkevich, A.V., Bruk, L.G., and Temkin, O.N., J. Phys. Chem. A, 1997, vol. 101, p. 9825.
Gorodskii, S.N., Zakharov, A.N., Kulik, A.V., Bruk, L.G., and Temkin, O.N., Kinet. Katal., 2001, vol. 42, no.2, p. 280.
Stromnova, T.A. and Moiseev, I.I., Usp. Khim., 1998, vol. 67, p. 542.
Vilar, R., Mingos, D.V.P., and Gardin, C.J., J. Chem. Soc., Dalton Trans., 1996, p. 4313.
Holloway, R.G., Penfold, B.R., Colton, R., and McCormick, M.J., J. Chem. Soc., Chem. Commun., 1976, p. 485.
Dervisi, A., Edwards, P.G., Neuman, P.D., Tooze, R.P., and Coles, S.J., J. Chem. Soc., Dalton Trans., 1998, p. 3771.
Manchot, W. and König, J., Chem. Ber., 1926, vol. 59, p. 883.
Gel'man, A. and Meilakh, E., Dokl. Akad. Nauk SSSR, 1942, vol. 36, p. 188.
Colton, R., McCormick, M.J., and Pannan, C.D., J. Chem. Soc., Chem. Commun., 1977, p. 823.
Stromnova, T.A. and Moiseev, I.I., J. Chem. Soc., Chem. Commun., 1978, p. 27.
Goggin, P.L., Goodfellow, R.J., Herbert, I.R., and Guy Orpen, A., J. Chem. Soc., Chem. Commun., 1978, p. 27.
Kulik, A.V., Bruk, L.G., Temkin, O.N., Aleksandrov, G.G., Nefedov, S.E., and Eremenko, I.L., Dokl. Akad. Nauk, 2002, vol. 42, p. 218.
Linev, V.P., Temkin, O.N., Polovnyak, V.K., Bruk, L.G., and Romanov, S.V., Zh. Obshch. Khim., 1981, vol. 51, p. 2536.
Feltham, R.D., Elbaze, G., and Ortega, R., Inorg. Chem., 1985, vol. 24, p. 1503.
Milstein, D. and Portnoy, M., Organometallics, 1994, p. 600.
Kulik, A.V., Bruk, L.G., Temkin, O.N., et al., Izv. Akad. Nauk (in press).
Bruk, L.G., Temkin, O.N., Goncharova, Z.V., Ustenkov, I.S., and Flid, V.R., React. Kinet. Catal. Lett., 1978, vol. 9, p. 303.
Wang, C., Bodenbinder, M., Willner, H., Retting, S., Trotter, J., and Aubke, F., Inorg. Chem., 1994, vol. 33, p. 779.
Xu, Q., Souma, Y., Umezawa, J., Tanaka, M., and Nakatani, H., J. Org. Chem., 1999, vol. 64, p. 6306.
Moiseev, I.I. and Pestrikov, S.V., Dokl. Akad. Nauk SSSR, 1966, vol. 171, p. 151.
Moiseev, I.I., Pestrikov, S.V., and Sverzh, S.V., Kinet. Katal., 1969, vol. 10, p. 74.
Davidson, J. and Triggs, C., J. Chem. Soc. A, 1968, p. 1324.
Chiusoli, G.P., Venturello, C., and Merzoni, S., Chem. Ind., 1968, p. 977.
Tsuji, J., Synthesis, 1990, no. 9, p. 739.
Klausner, A. and Jentsch, J.D., Applied Homogeneous Catalysis with Organometallic Compounds, Cornils, B. and Herrmann, W.A., Eds., Weinheim: VCH, 1996, vol. 1, p. 169.
Temkin, O.N., Kaliya, O.L., Zhir-Lebed', L.N., Golodov, V.A., Bruk, L.G., Mekhryakova, N.G., Gomogennoe okislenie (Homogeneous Oxidation), Alma-Ata: Nauka, 1978, vol. 17, p. 3.
Zhir-Lebed', L.N. and Temkin, O.N., Kinet. Katal., 1984, vol. 25, no.2, p. 316.
Zhir-Lebed', L.N. and Temkin, O.N., Kinet. Katal., 1984, vol. 25, no.2, p. 325.
Bruk, L.G. and Temkin, O.N., Khim. Prom-st., 1993, p. 57.
Bruk, L.G., Doctoral (Chem.) Dissertation, Moscow: Moskovskii Inst. Tonkoi Khim. Tekhnol. im. M.V. Lo-monosova, 1996.
Bruk, L.G., Vsesvyatskaya, N.Yu., Stromnova, T.A., Alekseeva, N.F., and Temkin, O.N., Zh. Organ. Khim., 1978, vol. 14, p. 473.
Shulyakovskii, G.M., Nyrkova, A.N., Pavlyuk, V.V., Khorkin, A.A., and Temkin, O.N., Kinet. Katal., 1982, vol. 23, p. 618.
Emel'yanova, G.R., Cand. Sci. (Chem.) Dissertation, Moscow: Moskovskii Inst. Tonkoi Khim. Tekhnol., 1984.
Bruk, L.G. and Temkin, O.N., Proc. 9th Soviet-Japanese Seminar on Catalysis, Novosibirsk, 1990, p. 83.
Bruk, L.G., Oshanina, I.V., Kozlova, A.P., Vorontsov, E.V., and Temkin, O.N., J. Mol. Catal., 1995, vol. 104, p. 9.
Bruk, L.G., Oshanina, I.V., Kozlova, A.P., Odintsov, K.Yu., and Temkin, O.N., Izv. Akad. Nauk, Ser. Khim., 1998, no. 6, p. 1104.
Bruk, L.G., Oshanina, I.V., Zakieva, A.S., and Temkin, O.N., Kinet. Katal., 1998, vol. 39, no.2, p. 183.
Gabriele, B., Costa, M., Salerno, G., and Chiusoli, G.P., J. Chem. Soc., Perkin Trans., 1994, vol. 1, p. 83.
Iwashita, Y., Tamura, F., and Wakamatsu, H., Bull. Chem. Soc. Jpn., 1970, vol. 43, no.5, p. 1520.
Temkin, O.N. and Bruk, L.G., Tez. dokl. III Vsesoyuz. konf. “Mekhanizm kataliticheskikh reaktsii” (Proc. III All-Union Conf. on the Mechanism of Catalystic Reactions), Novosibirsk: Nauka, 1982, vol. 2, p. 101.
Palyi, G., Varadi, G., and Horwath, I., J. Mol. Catal., 1981, vol. 13, p. 61; 1993, vol. 84, p. 7.
Joh, T., Doyama, K., Onitsuka, K., Shiohara, T., and Takahashi, S., Organometallics, 1991, vol. 10, p. 2493.
Fontaine, X.L.R., Jacobsen, G.B., Shaw, B.L., and Thornton-Pett, M., J. Chem. Soc., Chem. Commun., 1987, p. 662.
Bruk, L.G., Kozlova, A.P., Marshakha, O.V., Oshanina, I.V., Temkin, O.N., and Kaliya, O.L., Izv. Akad. Nauk, Ser. Khim., 1999, no. 10, p. 1899.
Drent, E., Arnoldy, D., and Budzelaar, P.H.M., J. Organomet. Chem., 1993, vol. 455, p. 247.
Drent, E., Arnoldy, D., and Budzellaar, P.H.M., J. Organomet. Chem., 1994, vol. 475, p. 57.
Scrivanti, A., Begnetto, V., Compagna, E., Zanato, M., and Matteoli, U., Organometallics, 1998, vol. 17, p. 630.
Kron, T.E., Terekhova, M.I., Noskov, Yu.G., and Petrov, E.S., Kinet. Katal., 2001, vol. 42, no.2, p. 204.
Begnetto, V., Scrivanti, A., Matteoli, U., Anronaroli, S., Scarpelli, R., and Grociani, B., J. Mol. Catal. A: Chem., 2001, vol. 170, p. 51.
Moiseev, I.I., Tez. dokl. XVI Mendeleevskogo s”ezda (Proc. XVI Mendeleev Congr.), St. Petersburg, 1998, vol. 1, p. 14.
Moiseev, I.I. and Vargaftik, M.N., New J. Chem., 1998, p. 1217.
Newman, P.D., Dervisi, A., Edwards, P.G., and Tooze, R.P., Proc. XXXIII ICCC, 1998, p. 515.
Tsuji, J., Takahashi, M., and Takahashi, T., Tetrahedron Lett., 1980, vol. 21, p. 849.
Zung, T.T., Bruk, L.G., and Temkin, O.N., Mendeleev Commun., 1994, no. 1, p. 2.
Bruk, L.G., Gorodsky, S.N., Zeigarnik, A.V., Valdes-Perez, R.E., and Temkin, O.N., J. Mol. Catal., A: Chem., 1998, vol. 130, p. 29.
Zung, T.T., Bruk, L.G., Malashkevich, A.V., and Temkin, O.N., Mendeleev Commun., 1995, no. 1, p. 3.
Belov, A.P., Satsko, N.G., and Moiseev, I.I., Kinet. Katal., 1972, vol. 13, p. 892.
Belov, A.P., Satsko, N.G., and Moiseev, I.I., Dokl. Akad. Nauk SSSR, 1972, vol. 202, p. 81.
Backvall, J.E., Pure Appl. Chem., 1992, vol. 64, p. 429.
Grennberg, H., Gogoll, A., and Backvall, J.E., Organometallics, 1993, vol. 12, p. 1790.
Roffia, P., Gregorio, G., Conti, F., Pregaglia, G.F., and Ugo, R., J. Mol. Catal., 1977, vol. 2, p. 191.
Selvakumar, K., Zapf, A., and Beller, M., Org. Lett., 2002, vol. 4, vol.18, p. 3031.
Selvakumar, K., Zapf, A., Spanenberg, A., and Beller, M., Chem. Eur. J., 2002, vol. 8, no.17, p. 3901.
Gillie, A. and Stille, J.K., J. Am. Chem. Soc., 1980, vol. 102, p. 4933.
Stille, J.K., The Chemistry of the Metal-Carbon Bond, Hartley F.R. and Patai, S., Eds. New York: Wiley, 1985, vol. 2, chapter 9, p. 625.
Grushin, V.V., Chem. Rev., 1996, vol. 96, no.6, p. 2011.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Temkin, O.N., Bruk, L.G. Palladium(II, I, 0) Complexes in Catalytic Reactions of Oxidative Carbonylation. Kinetics and Catalysis 44, 601–617 (2003). https://doi.org/10.1023/A:1026161103700
Issue Date:
DOI: https://doi.org/10.1023/A:1026161103700