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“Golden Age” of Homogeneous Catalysis Chemistry of Alkynes: Dimerization and Oligomerization of Alkynes

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Abstract

History of the development and use of homogeneous metal complex catalysts in the chemistry of acetylene and its derivatives is considered. Achievements of the catalytic chemistry of alkynes in the creation of affective catalytic systems (based on Groups 3—11 and 13 of the Periodic Table) for alkyne dimerization, capable of producing desired dimeric isomers possessing high chemo-, stereo- and regioselectivity are analyzed. The nature of elementary stages in four mechanisms of dimerization and the relations of the nature of organometallic intermediates to the nature of catalyst (metal and ligand), substrate, and type of mechanism, and, hence, to the selectivity of dimerization process are discussed.

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REFERENCES

  1. Temkin, O.N., Shestakov, G.K., and Treger, Yu.A., Atsetilen. Khimiya. Mekhanizmy reaktsii. Tekhnologiya (Acetylene. Chemistry. Reaction Mechanisms. Technology), Moscow: Khimiya, 1991.

  2. Tedeschi, R.J, Acetylene-Based Chemicals from Coal and Other Natural Resources, New York: Dekker, 1982.

    Google Scholar 

  3. Trofimov, B.A., Geteroatomnye proizvodnye atsetilena (Heteroatomic Derivatives of Acetylene), Moscow: Nauka, 1981.

  4. Trofimov, B.A., Acetylene and its derivatives in reactions with nucleophiles: recent advances and current trends, Curr. Org. Chem., 2002, vol. 6, no. 13, p. 1121.

    Article  CAS  Google Scholar 

  5. Trofimov, B.A. and Gusarova, N.K., Usp. Khim., 2007, vol. 76, no. 6, p. 550.

    Article  CAS  Google Scholar 

  6. Trofimov, B.A. and Shmidt, E.Yu., Russ. Chem. Rev., 2014, vol. 83, no. 7, p. 600.

    Article  CAS  Google Scholar 

  7. Salvio, R., Moliterno, M., and Bella, M., Alkynes in organocatalysis, Asian J. Org. Chem., 2014, vol. 3, p. 340.

    Article  CAS  Google Scholar 

  8. Temkin, O.N., Homogeneous Catalysis with Metal Complexes: Kinetic Aspects and Mechanisms, Chichester: Wiley, 2012.

    Book  Google Scholar 

  9. Acetylene Chemistry. Chemistry, Biology and Material Science, Diederich, F., Tykwinski, R.R., and Stang, R.J., Eds., Weinheim: Wiley, 2005.

    Google Scholar 

  10. Catalysis by Gold. Catal. Sci. Ser., Bond, G.C., Louis, C., and Thompson, D.T., Eds., London: Imperial College, 2006, vol. 6.

    Google Scholar 

  11. Modern Gold Supramolecular Chemistry. Gold-Metal Interactions and Applications, Laguna, A., Ed., Weinheim: Wiley, 2009.

    Google Scholar 

  12. Click Chemistry for Biotechnology and Materials Science, Lahann, J., Ed., Hoboken: Wiley, 2009, p. 432.

    Google Scholar 

  13. Gold Chemistry: Applications and Future Directions in the Life Sciences, Mohr, F., Ed., Weinheim: Wiley, 2009, p. 408.

    Google Scholar 

  14. Click Tiazoles. Topics in Heterocyclic Chemistry, Kosmrlj, J., Ed., Berlin: Springer–Verlag, 2012, Vol. 28.

    Google Scholar 

  15. Modern Gold Catalyzed Synthesis, Hashmi, A.S.K. and Toste, F.D., Eds., Weinheim: Wiley, 2012, p. 402.

    Google Scholar 

  16. Transition Metals Catalyzed Carbonylation Reactions, Beller, M. and Wu, X.-F., Eds., Berlin: Springer, 2013, p. 228.

  17. Maretina, I.A. and Ionin, B.I., Alkynes in Cycloadditions, Tebby, J.C., Ed., Chichester: Wiley, 2014, p. 312.

    Google Scholar 

  18. Modern Alkyne Chemistry. Catalytic and Atom-Economic Transformations, Trost, B.M. and Li, Ch.-J., Eds., Weinheim: Wiley, 2015, p. 424.

  19. Au-Catalyzed Synthesis and Functionalization of Heterocycles. Topics in Heterocyclic Chemistry, Bandini, M., Ed., Berlin: Springer, 2016, p. 289.

    Google Scholar 

  20. Lei, A., Shi, W., Liu, C., Liu, W., Zhang, H., and He, C., Oxidative Cross-Coupling Reactions, Weinheim: Wiley, 2017, p. 229.

    Google Scholar 

  21. Lu, W. and Zhou, L., Oxidation of C–H Bonds, Hoboken: Wiley, 2017, p. 508.

    Book  Google Scholar 

  22. Schore, N.E., Transition metal-mediated cycloaddition reactiones of alkynes in organic synthesis, Chem. Rev., 1988, vol. 88, p. 1081.

    Article  CAS  Google Scholar 

  23. Beletskaya, I. and Moberg, C., Element-element addition to alkynes catalyzed by the group 10 metals, Chem. Rev., 1999, vol. 99, p. 3435.

    Article  CAS  PubMed  Google Scholar 

  24. Chung, Y.K., Transition metal alkyne complexes: the Pauson–Khand reaction, Coord. Chem. Rev., 1999, vol. 188, p. 297.

    Article  Google Scholar 

  25. Kiss, G., Palladium-catalyzed Reppe carbonylation, Chem. Rev., 2001, vol. 101, no. 11, p. 3435.

    Article  CAS  PubMed  Google Scholar 

  26. Temkin, O. and Bruk, L., Oxidative Carbonylation-Homogeneous. Encyclopedia of Catalysis, Horvath, I., Ed., New York: Wiley, 2003, vol. 5, p. 394.

    Google Scholar 

  27. Negishi, E.-I. and Anastasia, L., Palladium-catalyzed alkynylation, Chem. Rev. 2003, vol. 103, p. 1979.

    Article  CAS  PubMed  Google Scholar 

  28. Beller, M., Seayad, J., Tillack, A., and Jiao, H., Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: recent developments and trends, Angew. Chem., 2004, vol. 43, p. 3368.

    Article  CAS  Google Scholar 

  29. Alonso, F., Beletskaya, I.P., and Yus, M. Transition-metal-catalyzed addition of heteroatom-hydrogen bond to alkynes, Chem. Rev., 2004, vol. 104, p. 3079.

    Article  CAS  PubMed  Google Scholar 

  30. Fűrstner, A. and Davies, P.W., Alkyne metathesis, Chem. Commun., 2005, p. 2307.

  31. Gabriele, B., Salerno, G., and Costa, M., Oxidative carbonylation, Top. Organomet. Chem., 2006, vol. 18, p. 232.

    Google Scholar 

  32. Hintermann, L. and Labonne, A., Catalytic hydration of alkynes and its application in synthesis, Synthesis, 2007, no. 8, p. 1121.

    Article  CAS  Google Scholar 

  33. Beletskaya, I.P. and Ananikov, V.P., Addition reactions of E–E and E–H bonds to triple bond of alkyne catalyzed by Pd, Pt and Ni complexes (E = S, Se), Pure Appl. Chem., 2007, vol. 79, p. 1041.

    Article  CAS  Google Scholar 

  34. Meldal, M. and Tornøe, C.W., Cu-catalyzed azide–alkyne cycloaddition, Chem. Rev., 2008, vol. 108, p. 2952.

    Article  CAS  PubMed  Google Scholar 

  35. Hein, C.D., Liu, X.-M., and Wang, D., Click chemistry a powerful tool for pharmaceutical sciences, Pharm. Res., 2008, vol. 25, no. 10, p. 2216.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  36. Hashmi, A.S.K., Homogeneous gold catalysis beyond assumptions and proposals – characterized intermediates, Angew. Chem., 2010, vol. 49, p. 5232.

    Article  CAS  Google Scholar 

  37. Hintermann, L., Recent developments in metal-catalyzed additions of oxygen nucleophiles to alkenes and alkynes, Top. Organomet. Chem., 2010, vol. 31, p. 123.

    Article  CAS  Google Scholar 

  38. Abbiati, G., Beccalli, E.M., and Rossi, E.,Groups 9 and 10 metals-catalyzed O–H bond addition to unsaturated molecules, Top. Organomet. Chem., 2013, vol. 43, p. 231.

    Article  CAS  Google Scholar 

  39. Schobert, H., Production of acetylene and acetylene-based chemicals from coal, Chem. Rev. 2014, vol. 114, no. 3, p. 1743.

    Article  CAS  PubMed  Google Scholar 

  40. Trotus, I.-T., Zimmermann, T., and Schüth, F., Catalytic reactions of acetylene: a feedstock for the chemical industry revisited, Chem. Rev., 2014, vol. 114, no. 3, p. 1761.

    Article  CAS  PubMed  Google Scholar 

  41. Chinchilla, R. and Nájera, C., Chemicals from alkynes with palladium catalysts, Chem. Rev. 2014, vol. 114, no. 3, p. 1783.

    Article  CAS  PubMed  Google Scholar 

  42. Quintero-Duque, S., Dyballa, K.M., and Fleischer, I., Metal-catalyzed carbonylation of alkynes: key aspects and recent development, Tetrahedron Lett., 2015, vol. 56, no. 21, p. 2634.

    Article  CAS  Google Scholar 

  43. Ananikov, V.P., Nickel: the “spirited horse” of transition metal catalysis, ACS Catal., 2015, no. 5, p.1964.

    Article  CAS  Google Scholar 

  44. Huple, D.B., Ghorpade, S., and Liu, R.-S., Recent advances in gold-catalyzed N- and O- functionalizations of alkynes with nitrones, nitroso, nitro and nitroxy species, Adv. Synth. Catal., 2016, vol. 358, p. 1348.

    Article  CAS  Google Scholar 

  45. Voronin, V.V., Ledovskaya, V.S., Bogachenkov, A.S., Rodygin, K.S., and Ananikov, V.P., Molecules, 2018, vol. 23, p. 2442.

    Article  PubMed Central  CAS  Google Scholar 

  46. Nieuwland, J.A. and Vogt, R.R., The Chemistry of Acetylene, New York: Reinhold, 1945.

    Google Scholar 

  47. Reppe, W., Neue Entwiclungen auf dem Gebiete der Chemie des Acetylene und Kohlen Oxydes, Berlin: Springer, 1949.

    Google Scholar 

  48. Johnson, A.W., The Chemistry of Acetylenic Compounds, London: Edward Arnold and Co., 1946, Vol. 1; 1950, Vol. 2.

  49. Raphael, R.A., Acetylenic Compounds in Organic Synthesis, New York: Academic Press, 1955, p. 219.

    Google Scholar 

  50. Ziegenbein, W., Einführungen der Ăthinyl- und Alkynyl-Gruppe in Organische Verbindungen, Berlin: Verlag Chemie, 1963.

    Google Scholar 

  51. Kotlyarevskii, I.L., Shvartsberg, M.S., and Fisher, L.B., Reaktsii atsetilenovykh soedinenii (Reaction of Acetylene Compounds), Novosibirsk: Nauka SB AS USSR, 1967, p. 354.

  52. Temkin, O.N. and Flid, R.M., Kataliticheskie prevrashcheniya atsetilenovykh soedinenii v rastvorakh kompleksov metallov (Catalytic Transformations of Acetylene Compounds in the Solutions of Metal Complexes), Moscow: Nauka, 1968, p. 212.

  53. Rudledge, T.F., Acetylenic Compounds: Preparation and Substitution Reaction, New York: Reinhold, 1968.

    Google Scholar 

  54. Khimiya atsetilenovykh soedinenii (Chemistry of Acetylene Compounds), Viie, G.G., Ed., Moscow: Khimiya, 1973.

    Google Scholar 

  55. Shostakovskii, M.F. and Bogdanova, A.V., The Chemistry of Diacetylenes, New York: Wiley, 1974.

    Google Scholar 

  56. Hanford, W.E. and Fuller, D.L., Acetylene chemistry, Ind. Eng. Chem., 1948, vol. 40, p. 1171.

    Article  CAS  Google Scholar 

  57. Copenhaver, J. and Bigelow, M., Acetylene and Carbon Monoxide Chemistry, New York: Reinhold, 1949.

    Google Scholar 

  58. Ustynyuk, Yu.A., Lektsii po organicheskoi khimii. Ch. 2. Khimiya uglevodorodov. Ser. Mir khimii (Lection on Organic Chemistry. Part 2. Chemistry of Hydrocarbons), Moscow: Tekhnosfera, 2016.

  59. Walker, L.F. and Landergan, T.E., US Patent 2487006, 1949; C.A., 1950, vol. 44, p. 5380.

  60. Kindler, K., Chem. Ber., 1921, vol. 54, p. 647.

    Article  Google Scholar 

  61. Fogel', I.G., Atsetilen, ego svoistva, izgotovlenie i primenenie (Acetylene, its Properties, Production and Application), Zal’kind, Yu., Ed., Leningrad: ONTI Goskhimtekhizdat, 1934.

  62. Flid, R.M. and Temkin, O.N., USSR Copyright Certificate 117494, 1958.

  63. Flid, R.M. and Temkin, O.N., Zh. Fiz. Khim., 1961, vol. 35, p. 452.

    CAS  Google Scholar 

  64. Halpern, I., James, B. R., and Kemp, A.L.W., J. Amer. Chem. Soc., 1961, vol. 83, p. 4097.

    Article  CAS  Google Scholar 

  65. Moiseev, I.I., π-Kompleksy olefinov v zhidkofaznom okislenii (π-Complexes of Olephynes in Liquid-Phase Oxidation), Moscow: Nauka, 1970, p. 270.

  66. Jira, R., Acetaldehyde from ethylene – a retrospective on the discovery of the Wacker process, Angew. Chem., 2009, vol. 48, p. 9034.

    Article  CAS  Google Scholar 

  67. Lines, C.B. and Long, R., Preprints Division of Petrol. Chem. Inc. Am. Chem. Soc., 1969, vol. 14, no. 2, p. 159.

    Google Scholar 

  68. Kaliya, O.L., Kirchenkova, G.S., Temkin, O.N., and Flid, R.M., Kinet. Katal., 1969, vol. 10, no. 5, p. 1186.

    CAS  Google Scholar 

  69. Kaliya, O.L., Temkin, O.N., Flid, R.M., Kimel’fel’d, Ya.M., Kirchenkova, G.S., and Smirnova, E.M., Izv. Akad. Nauk SSSR, Ser. Khim., 1969, p. 2854.

  70. Kimel’fel’d, Ya.M., Smirnova, E.M., Pershikova, N.I., Kaliya, O.L., and Temkin, O.N., Zh. Strukt. Khim., 1971, vol. 12, p. 1097.

    Google Scholar 

  71. Penella, F., Banks, R.L., and Bailey, G.C., J. Chem. Soc. Chem. Commun., 1968, p. 1548.

  72. Mogilyanskii, A.I., Kogan, L.M., Bondarenko, I.E., Kuleshova, L.S., and Temkin, O.N., Uchenye zapiski MITKhT im M.V.Lomonosova, 1970, vol. 1, no. 2, p. 10.

    CAS  Google Scholar 

  73. Chaltykian, O.A., Copper-Catalyzed Reactions, New York: Consultants Bureau, 1966.

    Google Scholar 

  74. Shmulevich, L.A., Razvitie khimii atsetilena, Extended Abstract of Cand. Sci. (Chem) Dissertation, Moscow: Institute of the History of Science and Technology AS USSR, 1969.

  75. Temkin, O.N., Bruk, L.G., and Zeigarnik, A.V., Kinet. Katal., 1993, vol. 34, no. 3, p. 445.

    CAS  Google Scholar 

  76. Zeigarnik, A.V., Bruk, L.G., Temkin, O.N., Likholobov, V.F., and Maier, L.I., Russ. Chem. Rev., 1996, vol. 65, p. 117.

    Article  Google Scholar 

  77. Temkin, O.N., Zeigarnik, A.V., and Bonchev, D., Chemical Reaction Networks. A Graph-Theoretical Approach, Boca Raton: CRC, 1996, p. 286.

    Google Scholar 

  78. Zeigarnik, A.V., Valdes-Perez, R.E., Temkin, O.N., Bruk, L.G., and Shalgunov, S.I., Organometallics, 1997, vol. 16, p. 3114.

    Article  CAS  Google Scholar 

  79. Norman, R.O.C., Parr, W.J.E., and Thomas, C.B., J. Chem. Soc. Perkin Trans., 1976, p. 1983.

  80. Fukuda, Y., Utimoto, K., and Nozaki, H., Heterocycles, 1987, vol. 25, p. 297.

    Article  CAS  Google Scholar 

  81. Hutchings, G.J., J. Catal., 1985, vol. 96, p. 292.

    Article  CAS  Google Scholar 

  82. Chiusoli, G.P., J. Organomet. Chem., 1986, vol. 300, p. 57.

    Article  CAS  Google Scholar 

  83. Grigoryan, E.A., Gyulumyan, Kh.R., Gurtovaya, E.I., Enikolopyan, N.S., and Ter-Kazaryan, M.A., Dokl. Akad. Nauk SSSR, 1981, vol. 257, no. 2, p. 364.

    CAS  Google Scholar 

  84. Noskova, N.F., Sokol’skii, D.V., Izteleulova, M.B., and Gafarova, N.A., Dokl. Akad. Nauk SSSR, 1982, vol. 262, no. 1, p. 113.

    CAS  Google Scholar 

  85. Shestakov, G.K., Temkin, O.N., Vsesvyatskaya, N.Yu., and Stepanov, A.M., Zh. Org. Khim., 1979, vol. 15, no. 2, p. 245.

    Google Scholar 

  86. Vsesvyatskaya, N.Yu., Shestakov, G.K., and Temkin, O.N., Kinet. Katal., 1986, vol. 27, p. 1330.

    CAS  Google Scholar 

  87. Sasaki, Y. and Dixneuf, P.H., J. Chem. Soc. Chem. Commun., 1986, p. 790.

  88. Chukhadzhyan, G.A., Abramyan, Zh.I., Kukolev, V.P., Gevorgyan, G.A., Tonyan, G.M., and Melkonyan, L.N., Armyan.Khim. Zh., 1978, vol. 31, no. 8, p. 607.

    CAS  Google Scholar 

  89. Sonogashira, K., Tohda, Y., and Hagihara, N., Tetrahedron Lett., 1975, p. 4467.

  90. Shestakov, G.K., Vasil’ev, A.M., Tishchenko, L.M., Temkin, O.N., and Flid, R.M., Kinet. Katal., 1974, vol. 15, no. 4, p. 1070.

    CAS  Google Scholar 

  91. Heck, R.F., J. Amer. Chem. Soc., 1972, vol. 94, p. 2712.

    Article  CAS  Google Scholar 

  92. Tsuji, J., Takahashi, M., and Takahashi, T., Tetrahedron Lett., 1980, vol. 21, p. 849.

    Article  CAS  Google Scholar 

  93. Bruk, L.G. and Temkin, O.N., Khim.Prom-sti, 1993, p. 57.

    Google Scholar 

  94. 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 Models of Liquid-Phase Reactions) Kiperman, S.L., Ed., Chernogolovka: IOC AS USSR, ICP AS USSR, 1985.

  95. Brailovskii, S.M., Kabalina, G.A., Shestakova, V.S., and Temkin, O.N., Zh. Org. Khim., 1977, vol. 13, p. 1158.

    CAS  Google Scholar 

  96. Shestakova, V.S., Brailovskii, S.M., and Temkin, O.N., Kinet. Katal., 1978, vol. 19, p. 1585.

    CAS  Google Scholar 

  97. Bruk, L.G., Vsesvyatskaya, N.Yu., Stromnova, T.A., Alekseeva, N.F., and Temkin, O.N., Zh. Org. Khim., 1978, vol. 14, p. 473.

    CAS  Google Scholar 

  98. Temkin, O.N., Mekhryakova, N.G., Bruk, L.G., Kaliya, O.L., and Prudnikov, A.Yu., Kinet. Katal., 1979, vol. 20, p. 629.

    Google Scholar 

  99. Temkin, O.N. and Bruk, L.G., Usp. Khim., 1983, vol. 52, p. 206.

    Article  CAS  Google Scholar 

  100. Mortreux, A. and Blanchard, M., Chem. Commun., 1974, p. 786.

  101. Kaliya, O.L., Temkin, O.N., Mekhryakova, N.G., and Flid, R.M., Dokl. Akad. Nauk SSSR, 1971, vol. 199, no. 6, p. 1321.

    CAS  Google Scholar 

  102. Bruk, L.G. and Temkin, O.N., Proc. 9th Soviet-Japan Seminar on Catalysis, Novosibirsk: Boreskov Institute of Catalysis SB RAS, 1990, p. 83.

  103. Bruk, L.G. Oshanina, I.V., Kozlova, A.P., Vorontsov, E.V., and Temkin, O.N., J. Mol. Catal., 1995, vol. 104, p. 9.

    Article  CAS  Google Scholar 

  104. Temkin, O.N. and Bruk, L.G., Kinet. Catal., 2003, vol. 44, no. 5, p. 601.

    Article  CAS  Google Scholar 

  105. Malashkevich, A.V., Bruk, L.G., and Temkin, O.N., J. Phys. Chem. A, 1997, vol. 101, no. 52, p. 9825.

    Article  CAS  Google Scholar 

  106. Gorodsky, S.N., Bruk, L.G., Istomina, A.E., Kurdiukov, A.V., and Temkin, O.N., Top. Catal., 2009, vol. 52, p. 557.

    Article  CAS  Google Scholar 

  107. Kozlov, A.I., Brailovskii, S.M., and Temkin, O.N., Kinet. Katal., 1994, vol. 35, no. 4, p. 551.

    CAS  Google Scholar 

  108. Kozlov, A.I., Brailovskii, S.M., and Temkin, O.N., Kinet. Katal., 1995, vol. 36, no. 2, p. 225.

    Google Scholar 

  109. Ananikov, V.P., Gayduk, K.A., Orlov, N.V., Beletskaya, I.P., Khrustalev, V.N., and Antipin, M.Yu., Chem. Eur. J., 2010, vol. 16, p. 2063.

    Article  CAS  PubMed  Google Scholar 

  110. Khemchyan, L.L., Ivanova, J.V., Zalesskiy, S.S., Ananikov, V.P., and Beletskaya, I.P., Adv. Synth. Catal., 2014, vol. 356, p. 771.

    Article  CAS  Google Scholar 

  111. Zalesskiy, S.S., Khrustalev, V.N., Kostukovich, A.Yu., and Ananikov, V.P., Organometallics, 2015, vol. 34, p. 5214.

    Article  CAS  Google Scholar 

  112. Drent, E., Arnoldy, D., and Budzelar, P.H.M., J. Organomet. Chem., 1993, vol. 455, p. 247.

    Article  CAS  Google Scholar 

  113. Drent, E., Arnoldy, D., and Budzelar, P.H.M., J. Organomet. Chem., 1994, vol. 475, p. 57.

    Article  CAS  Google Scholar 

  114. Doucet, H., Hofer, J., Bruneau, C., and Dixneuf, P.H., J. Chem. Soc. Chem. Commun., 1993, p. 850.

  115. Bruneau, C. and Dixneuf, P.H., Angew. Chem., 2006, vol. 45, p. 2176.

    Article  CAS  Google Scholar 

  116. Mitchenko, S.A. and Shubin, A.A., Metalloorganicheskie proizvodnye atsidokompleksov platiny: sintez, reaktsionnaya sposobnost' i dizain kataliticheskikh reaktsii (Organometallic Derivatives of Platinum Acid Complexes: Synthesis, Reactivity and Design of Catalytic Reactions), Donetsk: DonGUET, 2004.

  117. Dorel, R. and Echavarren, A., Chem. Rev., 2015, vol. 115, p. 9028.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  118. Schmidt, A., Halaiqa, A., and Smirnov, V.V., Synlett., 2006, no. 18, p. 2861.

  119. Eremin, D.B. and Ananikov, V.P., Understanding active species in catalytic transformations: from molecular catalysis to nanoparticles, leaching, “cocktails” of catalysts and dynamic systems, Coord. Chem. Rev., 2017, vol. 346, p. 2.

    Article  CAS  Google Scholar 

  120. Schmidt, A.F., Kurokhtina, A.A., and Larina, E.V., Mendeleev Commun., 2017, vol. 27, p. 213.

    Article  CAS  Google Scholar 

  121. Strauss, F., J. Liebig. Annalen Chem., 1905, vol. 342, no. 5, p. 190.

    Article  Google Scholar 

  122. Akhtar, M., Richards, T.A., and Weedon, B.C.L., J. Chem. Soc., 1959, p. 933.

  123. Mykhalichko, B.M., Temkin, O.N., and Mys’kiv, M.G., Russ. Chem. Rev., 2000, vol. 69, no. 11, p. 957.

    Article  CAS  Google Scholar 

  124. Gorin, D.J. and Toste, F.D., Nature, 2007, vol. 446, p. 395.

    Article  CAS  PubMed  Google Scholar 

  125. Soriano, E. and Marco-Contelles, J., Top. Curr. Chem., 2011, vol. 32, p. 1.

    Google Scholar 

  126. Zuccaccia, D., Belpassi, L., Rocchigiani, L., Tarantelli, F., and Macchioni, A., Inorg. Chem., 2010, vol. 49, p. 3080.

    Article  CAS  PubMed  Google Scholar 

  127. Das, A., Dash, C., Celik, M.A., Yousufuddin, M., Frenking, G., and Dias, R., Organometallics, 2013, vol. 32, p. 3135.

    Article  CAS  Google Scholar 

  128. Balcioglu, N., Uraz, I., Bozkurt, C., and Sevin, F., Polyhedron, 1997, vol. 16, no. 2, p. 327.

    Article  Google Scholar 

  129. Cornfield, P.W.R. and Shearer, H.M.M., Acta Crystallogr. Chem., 1966, vol. 21, p. 957.

    Article  Google Scholar 

  130. Temkin, O.N., Flid, R.M., Sukhova, T.G., Chepaikin, E.G., and Tikhonov, G.F., Zh. Prikl. Khim., 1968, vol. 41, p. 633.

    CAS  Google Scholar 

  131. Sukhova, T.G., Temkin, O.N., Flid, R.M., and Kaliya, T.K., Zh. Neorg. Khim., 1968, vol. 13, no. 8, p. 2073.

    CAS  Google Scholar 

  132. Sukhova, T.G., Borshch, N.Ya., Temkin, O.N., and Flid, R.M., Zh. Neorg. Khim., 1969, vol. 14, no. 3, p. 694.

    CAS  Google Scholar 

  133. Sukhova, T.G., Temkin, O.N., and Flid, R.M., Zh. Neorg. Khim., 1969, vol. 14, no. 4, p. 928.

    CAS  Google Scholar 

  134. Sukhova, T.G., Temkin, O.N., and Flid, R.M., Zh. Neorg. Khim., 1970, vol. 15, no. 7, p. 1849.

    CAS  Google Scholar 

  135. Nishiwaki, K.-ichiro, Kobayashi, M., Takeuchi, T., Matuoto, K., and Osakada, K., J. Mol. Catal. A: Chem., 2001, vol. 175, p. 73.

    Article  CAS  Google Scholar 

  136. Ahrland, S. and Rawstorne, J., Acta Chem. Scand., 1970, vol. 24, p. 157.

    Article  CAS  Google Scholar 

  137. Mykhalichko, B.M., Aksel’rud, L.G., and Davydov, V.N., Koord. Khim., 1997, vol. 42, no. 3, p. 410.

    Google Scholar 

  138. Tikhonov, G.F., Temkin, O.N., and Flid, R.M., Kinet. Katal., 1967, vol. 8, no. 3, p. 520.

    CAS  Google Scholar 

  139. Tikhonov, G.F., Temkin, O.N., and Flid, R.M., Zh. Fiz. Khim., 1966, vol. 11, no. 12, p. 3075.

    Google Scholar 

  140. Tikhonov, G.F., Shestakov, G.K., Temkin, O.N., and Flid, R.M., Zavod. Lab., 1967, vol. 33, no. 2, p. 150.

    CAS  Google Scholar 

  141. Temkin, O.N., Tikhonov, G.F., Flid, R.M., and Galeev, Yu.R., Kinet. Katal., 1967, vol. 8, no. 6, p. 1236.

    CAS  Google Scholar 

  142. Temkin, O.N., Flid, R.M., Shestakov, G.K., Ermakova, A., Tikhonov, G.F., Yarovaya, L.N., and Mikhal’chenko, V.G., Kinet. Katal., 1969, vol. 10, no. 6, p. 1231.

    Google Scholar 

  143. Shestakov, G.K., Tikhonov, G.F., Temkin, O.N., and Flid, R.M., Kinet. Katal., 1970, vol. 11, no. 3, p. 575.

    CAS  Google Scholar 

  144. Shestakov, G.K., Tikhonov, G.F., Temkin, O.N., Flid, R.M., Gershenzon, I.Sh., Brailovskii, S.M., and Dolzhnikova, S.I., Kinet. Katal., 1970, vol. 11, no. 4, p. 875.

    CAS  Google Scholar 

  145. Temkin, O.N., Shestakov, G.K., and Kozlova, N.Yu., Kinet. Katal., 1990, vol. 31, no. 4, p. 850.

    CAS  Google Scholar 

  146. Tikhonov, G.F., Shestakov, G.K., Temkin, O.N., and Flid, R.M., Kinet. Katal., 1966, vol. 7, no. 5, p. 614.

    Google Scholar 

  147. Temkin, O.N., O razlichnykh vzaimosvyazyakh kinetiki i termodinamiki (On the Various Relationships of Kinetics and Thermodynamics), Saarbrücken: Lambert Acad. Publ., 2016, p. 119.

    Google Scholar 

  148. Temkin, O.N., Sukhova, T.G., Shestakov, G.K., Tikhonov, G.F., Flid, R.M., Chepaikin, E.G., Novikova, G.M., and Borshch, N.Ya., Kinet. Katal., 1969, vol. 10, no. 5, p. 1004.

    CAS  Google Scholar 

  149. Brailovskii, S.M., Temkin, O.N., Flid, R.M., and Belova, N.G., Zh. Fiz. Khim., 1970, vol. 44, no. 4, p. 1112.

    CAS  Google Scholar 

  150. Brailovskii, S.M., Temkin, O.N., and Flid, R.M., Kinet. Katal., 1971, vol. 12, no. 5, p. 1152.

    CAS  Google Scholar 

  151. Osechkin, S.I., Mys’kiv, M.G., Zavalii, P.Yu., and Sobolev, A.N., Metalloorg. Khim., 1991, vol. 4, no. 5, p. 997.

    CAS  Google Scholar 

  152. Mykhalichko, B.M., Mys’kiv, M.G., and Aksel’rud, L.G., Koord. Khim., 1993, vol. 19, no. 9, p. 722.

    CAS  Google Scholar 

  153. Mys’kiv, M.G. and Mykhalichko, B.M., Zh. Srukt. Khim., 1994, vol. 35, no. 5, p. 120.

    Google Scholar 

  154. Mykhalichko, B.M., Mys’kiv, M.G., and Davydov, V.N., Zh. Neorg. Khim., 1999, vol. 44, no. 3, p. 411.

    CAS  Google Scholar 

  155. Mykhalichko, B.M. and Mys’kiv, M.G., Russ. J. Coord. Chem., 1998, vol. 24, no. 12, p. 880.

    CAS  Google Scholar 

  156. Mykhalichko, B.M., Russ. J. Inorg. Chem., 1998, vol. 43, no. 10, p. 1520.

    Google Scholar 

  157. Mykhalichko, B.M., Russ. J. Coord. Chem., 1999, vol. 25, no. 5, p. 336.

    CAS  Google Scholar 

  158. Mykhalichko, B.M., Mys’kiv, M.G., and Davydov, V.N., Russ. J. Inorg. Chem., 1999, vol. 44, no. 1, p. 40.

    Google Scholar 

  159. Mys'kiv, M.G., Zavalii, P.Yu., Mykhalichko, B.M., and Fundamenskii, V.S., Koord. Khim., 1988, vol. 14, no. 12, p. 1619.

    CAS  Google Scholar 

  160. Mykhalichko, B.M. and Mys’kiv, M.G., Koord. Khim., 1999, vol. 25, no. 5, p. 336.

    CAS  Google Scholar 

  161. Gamasa, M.P., Gimtno, J., and Lastra, E., J. Organomet. Chem., 1988, vol. 346, p. 277.

    Article  Google Scholar 

  162. Reger, D.L. and Huff, M.F., Organometallics, 1990, vol. 9, p. 2807.

    Article  CAS  Google Scholar 

  163. Osakoda, K., Takizawa, T., and Yamamoto, T., Organometallics, 1995, vol. 14, p. 3531.

    Article  Google Scholar 

  164. Reger, D.L., Collins, J.E., and Huff, M.F., Organometallics, 1995, vol. 14, p. 5475.

    Article  CAS  Google Scholar 

  165. Lang, H. and Weinmann, M., Synlett., 1995, p. 1.

  166. Normant, J.E. and Alexakis, A., Synthesis, 1981, p. 841.

  167. Vartanyan, V.S., Shestakov, G.K., and Temkin, O.N., Armyan.Khim. Zh., 1979, vol. 32, no. 4, p. 259.

    CAS  Google Scholar 

  168. Vartanyan, V.S., Shestakov, G.K., and Temkin, O.N, Armyan.Khim. Zh., 1979, vol. 32, no. 4, p. 264.

    CAS  Google Scholar 

  169. Tachiyama, T., Yoshida, M., Aoyagi, T., and Fukuzumi, S., Appl. Organomet. Chem., 2008, vol. 22, p. 205.

    Article  CAS  Google Scholar 

  170. Tachiyama, T., Yoshida, M., Aoyagi, T., and Fukuzumi, S., J. Phys. Org. Chem., 2008, vol. 21, p. 510.

    Article  CAS  Google Scholar 

  171. Hefner, J.G., Zizelman, P.M., Durfee, L.D., and Lewandos, G.S., J. Organomet. Chem., 1984, vol. 260, p. 369.

    Article  CAS  Google Scholar 

  172. Lieu, J., Zuo, Y., Han, M., Wang, Z., and Wang, D., J. Nat. Gas Chem., 2012, vol. 21, p. 495.

    Article  CAS  Google Scholar 

  173. Liu, J., Zuo, Y., Han, M., and Wang, Z., J. Chem. Technol. Biotechnol, 2013, vol. 88, p. 408. https://doi.org/10.1002/jctb.3860

    Article  CAS  Google Scholar 

  174. Sun, S., Kroll, J., Luo, Y., and Zhang, L., Synlett., 2012, vol. 23, p. 54.

    CAS  Google Scholar 

  175. Yamazaki, H.J., J. Chem. Soc. Chem. Commun., 1976, vol. 21, p. 841.

    Article  Google Scholar 

  176. Dahlberg, L., Frosin, K.-M., Kerstan, S., and Werner, D., J. Organomet. Chem., 1991, vol. 407, p. 115.

    Article  Google Scholar 

  177. Bianchini, C., Perruzzini, M., Zanobini, F., Frediani, P., and Albinati, A., J. Am. Chem. Soc., 1991, vol. 113, p. 5453.

    Article  CAS  Google Scholar 

  178. Bianchini, C., Frediani, P., Masi, D., Perruzzini, M., and Zanobini, F., Organometallics, 1994, vol. 13, p. 4616.

    Article  CAS  Google Scholar 

  179. Wakatsuki, Y. and Yamazaki, H., J. Am. Chem. Soc., 1991, vol. 113, p. 9604.

    Article  CAS  Google Scholar 

  180. Wakatsuki, Y. and Yamazaki, H., J. Organomet. Chem. 1995, vol. 500, p. 349.

    Article  CAS  Google Scholar 

  181. Slugovc, C., Mereiter, K., Zobetz, E., Schmid, R., and Kirchner, K., Organometallics, 1996, vol. 15, p. 5275.

    Article  CAS  Google Scholar 

  182. Yi, C.S. and Liu, N., Organometallics, 1996, vol. 15, p. 3968.

    Article  CAS  Google Scholar 

  183. Yi, C.S. and Liu, N., Synlett., 1999, no. 3, p. 281.

  184. Yi, C.S. and Liu, N., Organometallics, 1997, vol. 16, p. 3910.

    Article  CAS  Google Scholar 

  185. Yi, C.S. and Liu, N., Organometallics, 1998, vol. 17, p. 3158.

    Article  CAS  Google Scholar 

  186. Melis, K., Samulkiewicz, P., Rynkowski, J., and Verpoort, F., Tetrahedron Lett., 2002, vol. 43, p. 2713.

    Article  CAS  Google Scholar 

  187. Bassetti, M., Pasquini, C., Raneri, A., and Rosato, D., J. Org. Chem., 2007, vol. 72, p. 4558.

    Article  CAS  PubMed  Google Scholar 

  188. Katayama, H., Yari, H., Tanaka, M., and Ozawa, F., Chem. Commun., 2005, p. 4336.

  189. Chen, X., Xue, P., Sung, H.H.Y., Wiliams, I.D., Peruzzini, M., Bianchini, C., and Yia, G., Organometallics, 2005, vol. 24, p. 4330.

    Article  CAS  Google Scholar 

  190. Lee, J.-H. and Caulton, K.G., J. Organomet. Chem., 2008, vol. 693, p. 1664.

    Article  CAS  Google Scholar 

  191. Hijazi, A., Parkhomenko, K., Djukic, J.-P., and Chemmri, A., Adv. Synth. Catal., 2008, vol. 350, p. 1493.

    Article  CAS  Google Scholar 

  192. Dobson, A., Moore, D.S., Robinson, S.D., Hursthouse, M.B., and New, L., Polyhedron, 1985, vol. 4, p. 1119.

    Article  CAS  Google Scholar 

  193. Jia, G., Rheingold, A.L., and Meek, D.W., Organometallics, 1989, vol. 8, p. 1378.

    Article  CAS  Google Scholar 

  194. Wakatsuki, Y., Satoh, M., and Yamazaki, H., Chem. Lett., 1989, p. 1585.

    Article  Google Scholar 

  195. Bullock, R.M., J. Chem. Soc. Chem. Commun., 1989, p. 165.

  196. Tenorio, M.J., Puerta, M.C., and Valegra, P., J. Chem. Soc. Chem. Commun., 1991, p. 1750.

  197. Wakatsuki, Y., Koga, N., Yamazaki, H., and Morokama, K., J. Am. Chem. Soc., 1994, vol. 116, p. 8105.

    Article  CAS  Google Scholar 

  198. Yi, C.S. and Liu, N., Organometallics, 1997, vol. 16, p. 3729.

    Article  CAS  Google Scholar 

  199. Lee, H.M., Yao, J., and Jia, G., Organometallics, 1997, vol. 16, p. 3927.

    Article  CAS  Google Scholar 

  200. Bruneau, C. and Dixneuf, P.H., Acc. Chem. Res., 1999, vol. 32, p. 311.

    Article  CAS  Google Scholar 

  201. Bruce, M. and Wallis, R.C., Austr. J. Chem., 1979, vol. 32, p. 1471.

    Article  CAS  Google Scholar 

  202. Bruce, M., Chem. Rev., 1991, vol. 91, p. 197.

    Article  CAS  Google Scholar 

  203. Naota, T., Takaya, H., and Murahashi, S.-I., Chem. Rev. 1998, vol. 98, p. 2599.

    Article  CAS  PubMed  Google Scholar 

  204. Metal Vinylidens and Allenylidens in Catalysis: From Reactivity to Applications, Bruneau, Ch. and Dixneuf, P.H., Eds., Weinheim: Wiley, 2008.

    Google Scholar 

  205. Temkin, O.N. and Bruk, L.G., Ross. Khim. Zh., 2014, vol. 58, nos. 5–6, p. 90.

    Google Scholar 

  206. Esteruelas, M.A., Oro, L.A., and Ruiz, N., Organometallics. 1994, vol. 13, p. 1507.

    Article  CAS  Google Scholar 

  207. Barbaro, P., Bianchini, C., Peruzzini, M., and Polo, A., Inorg. Chem. Acta., 1994, vol. 220, p. 5.

    Article  CAS  Google Scholar 

  208. Gotzig, J., Otto, H., and Werner, H., J. Organomet. Chem., 1985, vol. 257, p. 247.

    Article  Google Scholar 

  209. Esteruelas, M.A., Herrero, J., Lopez, A.M., and Olivan, M., Organometallics, 2001, vol. 20, p. 3202.

    Article  CAS  Google Scholar 

  210. Alos, J., Bolaño, T., Esteruelas, M.A., Olivan, M., Oñate, E., and Valencia, M., Inorg. Chem., 2013, vol. 52, p. 6199.

    Article  CAS  PubMed  Google Scholar 

  211. Field, L.D., Messerle, B.A., Smernik, R.J., Hambley, T.W., and Turner, P., J. Chem. Soc. Dalton Trans., 1999, p. 2557.

  212. Midya, G.C., Paladhi, S., Dhara, K., and Dash, J., Chem. Commun., 2011, vol. 47, p. 6698.

    Article  CAS  Google Scholar 

  213. Midya, G.C., Paladhi, S., Dhara, K., and Dash, J., Org. Biomol. Chem., 2014, vol. 12, p. 1812.

    Article  CAS  PubMed  Google Scholar 

  214. Rivada-Wheelahan, O., Chakraborty, S., Shimon, L.J.W., Ben-David, Y., and Milstein, D., Angew. Chem., 2016, vol. 55, p. 6942.

    Article  CAS  Google Scholar 

  215. Bhunia, M., Sahoo, S., Vijakumar, G., Adhikari, D., and Mandal, S., Organometallics. 2016, vol. 35, p. 3775.

    Article  CAS  Google Scholar 

  216. Liang, Q., Osten, K.M., and Song, D., Angew. Chem., 2017, vol. 56, p. 1.

    Article  CAS  Google Scholar 

  217. Bauer, I. and Knölker, H.-J., Chem. Rev., 2015, vol. 115, p. 3170.

    Article  CAS  PubMed  Google Scholar 

  218. Singer, H. and Wilkinson, G., J. Chem. Soc. A, 1968, p. 849.

    Article  CAS  Google Scholar 

  219. Albano, P. and Aresta, M., J. Organomet. Chem., 1980, vol. 190, p. 243.

    Article  CAS  Google Scholar 

  220. Schāfer, H.-A., Marcy, R., Rüping, T., and Singer, H., J. Organomet. Chem., 1982, vol. 240, p. 17.

    Article  Google Scholar 

  221. Kovaler, I.P., Yerdakov, K.V., Strelenko, Yu.A., Vinogradov, M.G., and Nikishin, G.I., J. Organomet. Chem., 1990, vol. 386, p. 139.

    Article  Google Scholar 

  222. Boese, W.T. and Goldman, A.S., Organometallics, 1991, vol. 10, p. 782.

    Article  CAS  Google Scholar 

  223. Schāfer, M., Wolf, J., and Werner, H., J. Chem. Soc. Chem. Commun., 1991, p. 1341.

  224. Schāfer, M., Wolf, J., and Werner, H., J. Chem. Soc. Dalton Trans., 2005, p. 1468.

  225. Lee, C.-C., Lin, Y.-C., Liu, Y.-H., and Wang, Y., Organometallics, 2005, vol. 24, p. 136.

    Article  CAS  Google Scholar 

  226. Ito, J.-ichi, Kitase, M., and Nishiyama, H., Organometallics, 2007, vol. 26, p. 6412.

    Article  CAS  Google Scholar 

  227. Peng, H.M., Zhao, J., and Li, X., Adv. Synth. Catal., 2009, vol. 351, p. 1371.

    Article  CAS  Google Scholar 

  228. Mochizuki, K., Sakai, K., Kochi, T., and Kakiuchi, F., Synthesis, 2013, vol. 45, p. 2088.

    Article  CAS  Google Scholar 

  229. Rubio-Perez, L., Azpiroz, R., Di Giuseppe, A., Polo, V., Castarlenas, R., Perez-Torrente, J.J., and Oro, L.A., Chem. Eur. J., 2013, vol. 19, p. 15304.

    Article  CAS  PubMed  Google Scholar 

  230. Ogata, K. and Toyota, A., J. Organomet. Chem., 2007, vol. 692, p. 4139.

    Article  CAS  Google Scholar 

  231. Ghosh, R., Zhang, X., Achord, P., Emye, T.J., Krogh-Jespersen, K., and Goldman, A.S., J. Am. Chem. Soc., 2007, vol. 129, p. 853.

    Article  CAS  PubMed  Google Scholar 

  232. Field, L.D. and Ward, A.J., J. Organomet. Chem., 2003, vol. 681, p. 91.

    Article  CAS  Google Scholar 

  233. Hilt, G., Hess, W., Vogler, T., and Hengst, C., J. Organomet. Chem., 2005, vol. 690, p. 5170.

    Article  CAS  Google Scholar 

  234. Meriwether, L.S., Colthup, E.C., Kennerly, G.W., and Reusch, R.N., J. Org. Chem., 1961, vol. 26, p. 5155.

    Article  CAS  Google Scholar 

  235. Meriwether, L.S., Colthup, E.C., Kennerly, G.W., and Reusch, R.N., J. Org. Chem., 1961, vol. 26, p. 5163.

    Article  CAS  Google Scholar 

  236. Colthup, E.C. and Meriwether, L.S., J. Org. Chem., 1961, vol. 26, p. 5.

    Article  Google Scholar 

  237. Giacomelli, G., Caporusso, A.M., and Lardici, L., J. Org. Chem., 1979, vol. 44, p. 231.

    Article  CAS  Google Scholar 

  238. Ogoshi, S., Ueta, M., Oka, M., and Kurosawa, H., Chem. Commun., 2004, no. 23, p. 2732.

  239. Sabourin, E.T., J. Mol. Catal., 1984, vol. 26, p. 363.

    Article  CAS  Google Scholar 

  240. Trost, B.M., Sorum, M.T., Chan, C., Harms, A.E., and Rühter, G., J. Am. Chem. Soc., 1997, vol. 119, p. 698.

    Article  CAS  Google Scholar 

  241. Canty, A.J., Acc. Chem. Res., 1992, vol. 25, p. 83.

    Article  CAS  Google Scholar 

  242. Herrmann, W.A., Böhm, V.P.W., Gstöttmayr, G.V.K., Grosche, M., Reisinger, C.-C., and Weskamp, T., J. Organomet. Chem., 2001, vols. 617–628, p. 616.

  243. Rubina, M. and Gevorgyan, V., J. Organomet. Chem., 2001, vol. 123, p. 11107.

    CAS  Google Scholar 

  244. Yang, C. and Nolan, S.P., J. Org. Chem., 2002, vol. 67, p. 591.

    Article  CAS  PubMed  Google Scholar 

  245. Jahier, C., Zatolochnaya, O.V., Zvyagintsev, N.V., Ananikov, V.P., and Gevorgyan, V., Org. Lett., 2012, vol. 14, p. 2846.

    Article  CAS  PubMed  Google Scholar 

  246. Tohda, Y., Sonogashira, K., and Hagihara, N., J. Organomet. Chem., 1976, vol. 110, p. 53.

    Article  Google Scholar 

  247. Yasuda, T., Kai, Y., Yasuoka, N., and Kasai, N., Bull. Chem. Soc. Jpn., 1977, vol. 50, no. 11, p. 2888.

    Article  CAS  Google Scholar 

  248. Zatolochnaya, O.V., Gordeev, E.G., Jahier, C., Ananikov, V.P., and Gevorgyan, V., Chem. Eur. J., 2014, vol. 20, p. 9578.

    Article  CAS  PubMed  Google Scholar 

  249. Chen, T., Guo, C., Goto, M., and Han, L.-B., Chem. Commun., 2013, vol. 49, p. 7498.

    Article  CAS  Google Scholar 

  250. Chen, R., Chen, T., Zhao, Y., Qiu, R., Zhou, Y., Yin, S., Wang, X., Goto, M., and Han, L.-B., J. Am. Chem. Soc., 2011, vol. 133, p. 17037.

    Article  PubMed  CAS  Google Scholar 

  251. Kawata, A., Kuninobu, Y., and Takai, K., Chem. Lett., 2009, vol. 38, p. 836.

    Article  CAS  Google Scholar 

  252. Hagihara, N., Tamura, M., Yamazaki, H., and Fujiwara, M., Bull. Chem. Soc. Jpn., 1961, vol. 34, p. 892.

    Article  CAS  Google Scholar 

  253. Akita, N., Yasuda, H., and Nakamura, A., Bull. Chem. Soc. Jpn., 1984, vol. 57, p. 480.

    Article  CAS  Google Scholar 

  254. Horton, A.D., J. Chem. Soc. Chem. Commun., 1992, p. 185.

  255. Platel, R.H. and Schafer, L.L., Chem. Commun., 2012, vol. 48, p. 10609.

    Article  CAS  Google Scholar 

  256. Thompson, M.E., Baxter, S.M., Bulls, A.R., Burger, B.J., Nolan, M.C., Santarsiero, B.D., Schaefer, W.P., and Bercaw, J.E., J. Am. Chem. Soc., 1987, vol. 109, p. 203.

    Article  CAS  Google Scholar 

  257. St. Clair, M., Schaefer, W.P., and Bercaw, J.E., Organometallics, 1991, vol. 10, p. 525.

    Article  CAS  Google Scholar 

  258. Den Haan, K.H., Wielstra, Y., and Teuben, J.H., Organometallics, 1987, vol. 6, p. 2053.

    Article  CAS  Google Scholar 

  259. Heeres, H.J. and Teuben, J.H., Organometallics, 1991, vol. 10, p. 1980.

    Article  CAS  Google Scholar 

  260. Evans, W.J., Keyer, R.A., and Ziller, J.W., Organometallics, 1990, vol. 9, p. 2628.

    Article  CAS  Google Scholar 

  261. Evans, W.J., Keyer, R.A., and Ziller, J.W., Organometallics, 1993, vol. 12, p. 2618.

    Article  CAS  Google Scholar 

  262. Nishiura, M., Hou, Z., Wakatsuki, Y., Yamaki, T., and Miyamoto, T., J. Am. Chem. Soc., 2003, vol. 125, p. 1184.

    Article  CAS  PubMed  Google Scholar 

  263. Nishiura, M. and Hou, Z., J. Mol. Catal. A: Chem., 2004, vol. 213, p. 101.

    Article  CAS  Google Scholar 

  264. Ge, S., Quiroga Narambuena, V.F., and Hessen, B., Organometallics, 2007, vol. 26, p. 6508.

    Article  CAS  Google Scholar 

  265. Haskel, A., Straub, T., Dash, A.K. and Eisen, M.S., J. Am. Chem. Soc., 1999, vol. 121, p. 3014.

    Article  CAS  Google Scholar 

  266. Haskel, A., Wang, J.Q., Straub, T., Neyroud, T.G., and Eisen, M.S., J. Am. Chem. Soc., 1999, vol. 121, p. 3025.

    Article  CAS  Google Scholar 

  267. Dash, A.K., Wang, J.S., Berthet, J.C., Ephritikhine, M., and Eisen, M.S., J. Organomet. Chem., 2000, vol. 604, p. 83.

    Article  CAS  Google Scholar 

  268. Dash, A.K., Gourevich, I., Wang, J.Q., Wang, J., Kapon, M., and Eisen, M., Organometallics, 2001, vol. 20, p. 5084.

    Article  CAS  Google Scholar 

  269. Dash, A. and Eisen, M.S., Org. Lett., 2000, vol. 2, p. 737.

    Article  CAS  PubMed  Google Scholar 

  270. Schmidbaur, H. and Schier, A., Organometallics, 2010, vol. 20, p. 2.

    Article  CAS  Google Scholar 

  271. Yakobson, V.V., Geskin, V.M., Klimenko, N.M., Bozhenko, K.V., and Temkin, O.N., Teor. Eksp. Khim., 1985, no. 3, p. 303.

  272. Klimenko, N.M., Bozhenko, K.V., Strumina, E.V., Rykova, E.A., and Temkin, O.N., J. Mol. Struct. (THEOCHEM), 1999, vol. 490, p. 233.

    Article  CAS  Google Scholar 

  273. Temkin, O.N., Kinet. Catal., 2014, vol. 55, no. 2, p. 172.

    Article  CAS  Google Scholar 

  274. McDade, Ch. and Bercaw, J.E., J. Organomet. Chem., 1985, vol. 279, p. 281.

    Article  CAS  Google Scholar 

  275. Frohnapfel, D.S. and Templeton, J.L., Coord. Chem. Rev., 2000, vols. 206–207, p. 199.

    Article  Google Scholar 

  276. Antonova, A.B., Kolobova, N.E., Petrovsky, P.V., Lokshin, B.V., and Obezyuk, N.S., J. Organomet. Chem., 1977, vol. 137, p. 55.

    Article  CAS  Google Scholar 

  277. Kolobova, N.E., Antonova, A.B., Khitrova, O.M., Antipin, M.Yu., and Struchkov, Yu.T., J. Organomet. Chem., 1977, vol. 137, p. 69.

    Article  CAS  Google Scholar 

  278. Antonova, A.B. and Ioganson, A.A., Usp. Khim., 1989, vol. 58, p. 1197.

    Article  CAS  Google Scholar 

  279. De Angelis, F. and Sgamellotti, A., Organometallics, 2002, vol. 21, no. 13, p. 2715.

    Article  CAS  Google Scholar 

  280. De Angelis, F., Sgamellotti, A., and Re, N., Organometallics, 2002, vol. 21, no. 26, p. 5944.

    Article  CAS  Google Scholar 

  281. Grotjahn, D.B., Zeng, Xi., Cooksy, A.L., Scott Kassel, W., DiPasquale, A.G., Zakharov, L.N., and Rheingold, A.L., Organometallics, 2007, vol. 26, no. 14, p. 3385.

    Article  CAS  Google Scholar 

  282. De Angelis, F., Sgamellotti, A., and Re, N., Organometallics, 2007, vol. 26, no. 14, p. 5285.

    Article  CAS  Google Scholar 

  283. Vastine, B.A. and Hall, M., Organometallics, 2008, vol. 27, p. 4325.

    Article  CAS  Google Scholar 

  284. Tenorio, M.J., Puerta, M.C., Valegra, P., Ortuno, M.A., Ujaque, G., and Llendos, A., Inorg. Chem., 2013, vol. 52, p. 8919.

    Article  CAS  Google Scholar 

  285. Olivan, M., Clot, E., Eisenstein, O., and Caulton, K.G., Organometallics, 1998, vol. 17, no. 14, p. 3091.

    Article  CAS  Google Scholar 

  286. Buil, M.L., Eisenstein, O., Esteruelas, M.A., Garsia-Yebra, C., Gutierrez-Puebla, E., Olivan, M., Onate, E., Ruiz, N., and Tajada, M., Organometallics, 1999, vol. 18, p. 4949.

    Article  CAS  Google Scholar 

  287. Bassetti, M., Cadierno, V., Gimeno, J., and Pasquini, C., Organometallics, 2008, vol. 27, no. 19, p. 5009.

    Article  CAS  Google Scholar 

  288. Muthoh, Y., Imai, K., Kimura, Y., Ikeda, Y., and Ishii, Y., Organometallics, 2011, vol. 30, p. 204.

    Article  CAS  Google Scholar 

  289. Salvio, R., Julia-Hernandez, F., Pisciottni, L., Mendoza-Merono, R., Garcia-Granda, S., and Bassetti, M., Organometallics, 2017, vol. 36, no. 19, p. 3830.

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The author is grateful to Karen Egiazaryan, student of the MIREA – Russian Technological University (Moscow), for his help in graphical presentation of this review.

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Correspondence to O. N. Temkin.

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Dedicated to “Kinetika i Kataliz” journal on its 60 Years Edition Anniversary, and to academician I.I. Moiseev, one of the creators of modern catalysis with metal complexes, on his 90th birthday

Translated by P. Pozdeev

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Temkin, O.N. “Golden Age” of Homogeneous Catalysis Chemistry of Alkynes: Dimerization and Oligomerization of Alkynes. Kinet Catal 60, 689–732 (2019). https://doi.org/10.1134/S0023158419060120

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  • DOI: https://doi.org/10.1134/S0023158419060120

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