Abstract
The most recent data on reactions involving the formation of heterocycles that take place in the presence of palladium, nickel, cobalt, and iron complexes are examined. The mechanisms of the reactions are discussed in the light of modern concepts of catalysis by metal complexes. The particular significance of metal complex catalysts for the synthesis of heterocycles with unique structures is demonstrated.
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Literature cited
A. Kashara, T. Isumi, K. Sato, M. Maemura, and T. Hayasaka, Bull. Chem. Soc. Jpn.,50, 1899 (1977).
D. Korte, L. Hegedus, and R. Wirth, J. Org. Chem.,42, 1329 (1977).
T. Hosokawa, K. Maeda, and J. Moritani, Tetrahedron Lett., No. 10, 739 (1973).
T. Hosokawa, H. Ohkata, and J. Moritani, Bull. Chem. Soc. Jpn.,48, 1533 (1975).
I. I. Moiseev, π Complexes in Liquid-Phase Oxidation [in Russian], Nauka, Moscow (1970).
P. Maitlis, The Organic Chemistry of Palladium, Vol. 2, Academic Press, New York (1971), p. 76.
A. Kasahara, T. Izmui, and M. Ooshima, Bull. Chem. Soc. Jpn.,47, 2526 (1974).
L. Nahum, J. Org. Chem.,33, 3601 (1968).
Y. Falbe, H. Huppes, and F. Korte, Chem. Ber.,97, 1104 (1964).
J. Falbe, Carbon. Monoxide in Organic Synthesis, Springer-Verlag (1970).
A. N. Nesmeyanov (ed.), Organic Syntheses through Metal Carbonyls [in Russian], Mir, Moscow (1970).
J. Wender and P. Pino (eds.), Organic Synthesis through Metal Carbonyls, Vol. 2, Wiley, New York-London (1977).
C. Bird, J. Organometal. Chem.,47, 281 (1973).
E. Schmitz, A. Striegler, R. Urban, and G. Zimmermann, East German Patent No. 96943 (1973); Ref. Zh. Khim., 18N113P (1975).
E. Schmitz, R. Urban, U. Heuck, G. Zimmermann, and E. Gründemann, J. Prakt. Chem.,318, 185 (1976).
R. Lugo, Aspects of Homogeneous Catalysis: A Series of Advances, Reidel Publishing (1970).
K. Maeda, T. Hosokawa, Sh.-Y Marahashi, and Y. Moritani, Tetrahedron Lett., No. 51, 5075 (1973).
T. Hosokawa, N. Shimo, K. Maeda, A. Sonoda, and Sh.-Y. Maruhashi, Tetrahedron Lett., No. 5, 383 (1976).
L. Hegedus, G. Allen, and E. Waterman, J. Am. Chem. Soc.,98, 2674 (1976).
M. Mori and J. Ban, Tetrahedron Lett., No. 21, 1803 (1976).
B. Bogdanovic, P. Heimbach, M. Kröner, and G. Wilke, Ann.,727, 143 (1969).
M. Mori and J. Ban, Tetrahedron Lett., No. 21, 1807 (1976).
M. Mori, K. Chiba, and J. Ban, Tetrahedron Lett., No. 12, 1037 (1977).
H. Yoshimoto and H. Itatani, Bull. Chem. Soc. Jpn.,46, 2490 (1973).
B. Akermark, L. Eberson, E. Jonnsson, and E. Pattersson, J. Org. Chem.,40, 1365 (1975).
B. Trost and J. Genet, J. Am. Chem. Soc.,98, 8516 (1976).
B. Trost, Tetrahedron,33, 2615 (1977).
P. Heimbach, P. Jolly, and G. Wilke, Adv. Organometal. Chem.,8, 1970.
P. Jolly and G. Wilke, The Organic Chemistry of Nickel, Academic Press, New York (1974).
P. Maitlis, The Organic Chemistry of Palladium, Vol. 1, Academic Press, New York (1971).
P. Heynes, Tetrahedron Lett., No. 42, 3687 (1970).
R. Manyik, W. Walker, K. Atkins, and E. Hammack, Tetrahedron Lett., No. 43, 3813 (1970).
A. De Smet and M. Anteunis, Org. Magn. Res.,5, 589 (1973).
K. Ohno, T. Mitsuyasu, and J. Tsuji, Tetrahedron Lett., No. 1, 67 (1971).
K. Ohno, T. Mitsuyasu, and J. Tsuji, Tetrahedron,28, 3705 (1972).
Tsumura Ryuitiro and Madzaki Takaaki, Japanese Patent No. 1291 (1969); Ref. Zh. Khim., 15N136P (1972).
W. Friedrichsen and O. Goehre, US Patent No. 3576011 (1968); Ref. Zh. Khim., 4N22P (1971).
H. Watanabe, K. Maiudzaki, R. Tsumura, and T. Madzaki, Japanese Patent No. 48-6463 (1973); Ref. Zh. Khim., 24N171P (1973).
K. Ohno and J. Tsuji, Chem. Commun., No. 6, 247 (1971).
J. Kiji, K. Yamamoto, H. Tomita, and J. Furukawa, Chem. Commun., No. 13, 506 (1974).
G. A. Tolstikov, U. M. Dzhemilev, F. A. Selimov, I. Kh. Aminev, and E. M. Vyrypsev, Zh. Org. Khim.,13, 885 (1977).
U. M. Czhemilev, F. A. Selimov, E. G. Galkin, and G. A. Tolstikov, Izv. Akad. Nauk, SSSR, Ser. Khim., No. 6, 1359 (1977).
U. M. Dzhemilev, Doctoral Dissertation, Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow (1978).
U. M. Dzhemilev, L. Yu. Gubaidullin, and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1469 (1978).
H. Peter and D. Reinehr, Helv. Chim. Acta,61, 1115 (1978).
D. Reinehr, Helv. Chim. Acta,61, 1122 (1978).
P. Heimbach, B. Hugelin, H. Peter, A. Kolott, and E. Troxler, Angew. Chem.,88, 29 (1976).
A. Kolott, Dissertation, Ruhr Universität, Bochum (1976).
L. Yu. Gubaidullin, Master's Dissertation, Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa (1979).
G. A. Tolstikov, U. M. Dzhemilev, L. Yu. Gubaidullin, and I. Kh. Aminev, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2151 (1974).
G. A. Tolstikov, U. M. Dzhemilev, and L. Yu. Gubaidullin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1609 (1976).
G. A. Tolstikov, U. M. Dzhemilev, and L. Yu. Gubaidullin, Zh. Org. Khim.,12, 1645 (1976).
U. M. Dzhemilev, L. Yu. Gubaidullin, and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1469 (1978).
U. M. Dzhemilev, G. A. Tolstikov, L. Yu. Gubaidullin, R. V. Kunakova, and F. A. Selimov, Material from the Fifth All-Union Conference on Catalytic Reactions in the Liquid Phase, Alma Ata [in Russian], Vol. 4 (1978), p. 97.
R. Backer and M. Nobbs, Tetrahedron Lett., No. 42, 3759 (1977).
P. Heimbach, Angew, Chem., Int. Ed.,12, 975 (1973).
R. Meyer, Dissertation, Ruhr Universität, Bochum (1973).
U. M. Dzhemilev, R. V. Kinakova, F. V. Sharipova, L. V. Spirikhin, L. M. Khalilov, E. V. Vasil'eva, and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 600 (1979).
F. V. Sharipova, and R. V. Kunakova, Summaries of Papers Presented by Young Scientists [in Russian], Bashkir Branch, Academy of Sciences of the USSR, Ufa (1979), p. 21.
G. A. Tolstikov, U. M. Dzhemilev, R. V. Kunakova, F. Ya. Kanzafarov, Yu. A. Sangalov, and F. V. Sharipova, in: Catalytic Synthesis of Organic Sulfur Compounds [in Russian], Institute of Catalysis, Siberian Branch, Academy of Sciences of the USSR, Novosibirsk (1979), p. 15.
H. Sukurai., J. Kamiyama, and N. Jasahira, Chem. Lett., No. 8, 887 (1975).
W. Hafner, H. Prigge, and J. Smidt, Ann.,693, 109 (1966).
J. Watkasuki and H. Jamazaki, Tetrahedron Lett., No. 36, 3383 (1973).
H. Bönnemann, R. Brinkmann, and H. Benkluhn, Synthesis, No. 8, 575 (1974).
H. Bönnemann and R. Brinkmann, Synthesis, No. 9, 600 (1975).
H. Bönnemann, Angew. Chem.,90, 517 (1978).
J. Kusinoki and H. Okazaki, Hydrocarbon Process, No. 11, 129 (1974).
R. Noyori, J. Baba, S. Makino, and H. Takaya, Tetrahedron Lett., No. 20, 1741 (1973).
H. Takaya, J. Hakagawa, S. Makino, and R. Noyori, J. Am. Chem., Soc.,100, 1778 (1978).
H. Takaya, J. Hagakawa, S. Makino, and R. Noyori, J. Am. Chem. Soc.,100, 1786 (1978).
R. Noyori, J. Hakagawa, H. Takaya, S. Murai, R. Kobayashi, and N. Sonoda, J. Am. Chem. Soc.,100, 1759 (1978).
R. Funk and K. Vollhardt, J. Am. Chem. Soc.,98, 6755 (1976).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 147–163, February, 1980.
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Tolstikov, G.A., Dzhemilev, U.M. Synthesis of heterocyclic compounds in the presence of transition metal complexes (review). Chem Heterocycl Compd 16, 99–113 (1980). https://doi.org/10.1007/BF00554196
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DOI: https://doi.org/10.1007/BF00554196