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Catalytic intermolecular hydrogen transfer in the hydrogenation of heterocyclic aldehydes and ketones. A review

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Literature data and the investigation results of the present authors on the reduction of heterocyclic aldehydes and ketones using catalytic hydrogen transfer have been analyzed.

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References

  1. I. S. Kolomnikov, V. P. Kukoiev, and M. E. Vol'pin, Usp. Khim.,53, No. 5, 903 (1974).

    Google Scholar 

  2. G. Brieger and T. J. Nestrick, Chem. Rev.,74, No. 5, 567 (1974).

    Google Scholar 

  3. R. A. W. Johnstone, A. H. Wilby, and J. D. Entwistle, Chem. Rev.,85, 129 (1985).

    Google Scholar 

  4. Pillai S. Muthukumaru, J. Sci. Ind. Res.,47, 460 (1988).

    Google Scholar 

  5. T. Nishiguchi, K. Tanaka, and K. Fukuzumi, J. Organometali., Chem.,193, 37 (1980).

    Google Scholar 

  6. V. Z. Sharf, L. Kh. Freidlin, and V. N. Krutii, Izv. Akad. Nauk SSSR Ser. Khim.,10, 2264 (1973).

    Google Scholar 

  7. V. Z. Sharf, L. Kh. Freidlin, and V. N. Krutii, Izv. Akad. Nauk SSSR Ser. Khim.,4, 735 (l977).

    Google Scholar 

  8. A. Camus, G. Mestroni, and G. Zassinovich, J. Mol. Catal.,6, 231 (1979).

    Google Scholar 

  9. Y. Sasson and J. Blum, Tetrahedron Lett., No.24, 2167 (1971).

    Google Scholar 

  10. G. Descotes, J. P. Praly, and D. Sinou, J. Mol. Catal.,6, 421 (1979).

    Google Scholar 

  11. J. Blum., J. Mol. Catal.,3, 33 (1977).

    Google Scholar 

  12. T. Tatsumi, K. Kizawa, and H. Tominaga, Chem. Lett., No. 2, 191 (1977).

  13. H. Imai, T. Nishiguchi, and K. Fukuzumi, J. Org. Chem.,41, No. 4, 665 (1976).

    Google Scholar 

  14. Y. Blum, Y. Sasson, and S. Iflah, Tetrahedron Lett., No. 11, 1015 (l972).

  15. Y. C. Orr, M. Mersereanu, and A. Sanford, J. Chem. Soc. Chem. Commun., No. 1, 162 (1970).

  16. T. A. Smith and P. M. Maitlis, J. Organometall. Chem.,289, 385 (1985).

    Google Scholar 

  17. H. B. Henbest and Z. Zurgiyah, J. Chem. Soc. Perkin Trans. I, No. 5, 604 (1974).

  18. Y. Sasson, P. Albin, and J. Blum, Tetrahedron Lett., No. 10, 833 (1974).

  19. B. T. Khai and A. Arcelli, Tetrahedron Lett.,26, No. 28, 3365 (l985).

    Google Scholar 

  20. Y. Sasson and J. Blum., J. Org. Chem.,40, No. 13, 1887 (1975).

    Google Scholar 

  21. V. Z. Sharf, L. Kh. Freidlin, V. N. Krutii, and T. V. Lysyak, Izv. Akad. Nauk SSSR Ser. Khim., No. 10, 2195 (1972).

  22. A. Camus, G. Mestroni, and G. Zassinovich, J. Organometall. Chem.,184, C10 (1980).

    Google Scholar 

  23. G. Descotes and I. Sabadie, J. Mol. Catal., 5, 415 (1979).

    Google Scholar 

  24. B. T. Khai and A. Arcelli, J. Org. Chem.,54, 949 (1989).

    Google Scholar 

  25. Y. Watanabe, T. Ohta, and Y. Tsuji, Bull. Chem. Soc. Japan,55, 2441 (1982).

    Google Scholar 

  26. G. Speir and L. Marko, J. Organometali. Chem.,210, 253 (1981).

    Google Scholar 

  27. Zh. G. Yuskovets and M. V. Shimanskaya, “Use of metal complex catalysis in organic synthesis," Abstracts of the First All-Union Conference, Ufa (1989), p. 49.

  28. Zh. G. Yuskovets and M. V. Shimanskaya, Khim. Geterotsikl. Soedin., No. 6, 745 (1990).

  29. H. Imai, T. Nishiguchi, and K. Fukuzumi, Chem. Lett., No. 8, 807 (1975).

  30. G. Brieger and T.-H. Fu, J. Chem. Soc. Chem. Commun., No. 19, 757 (1976).

  31. G. Wit, J. J. Vlieger, A. C. K. Dalen, A. P. G. Kiebom, and H. Bekkum, Tetrahedron Lett., No. 15, 1327 (l978).

  32. G. P. Boldrini, D. Savoia, E. Tagliavini, G. Trombini, and A. Umani-Ronchi, J. Org. Chem.,50, 3082 (1985).

    Google Scholar 

  33. M. J. Andrews and C. N. Pillai, Indian J. Chem.,16, No. 5, 465 (l978).

    Google Scholar 

  34. É. Lukevits, L. M. Ignatovich, Zh. G. Yuskovets, L. O. Golender, and M. V. Shimanskaya, Zh. Obshch. Khim.,57, No. 6, 1294 (1987).

    Google Scholar 

  35. G. Tragale, M. Gargano, and M. Rossi, J. Mol. Catal.,58, No. 5, 69 (1979).

    Google Scholar 

  36. A. Benyei and F. Joo, J. Mol. Catal.,58, No. 2, 151 (1990).

    Google Scholar 

  37. Y. Sasson and G. L. Rempel, Tetrahedron Lett., No. 36, 3221 (1974).

  38. I. S. Kolomnikov, I. L. Nakhshunova, F. Prukhnik, N. A. Belikova, and M. E. Vol'pin, Izv. Akad. Nauk SSSR Ser. Khim., 5, 1180 (1972).

    Google Scholar 

  39. H.-A. Bruner, J. Unsin, R. Hemmer, and M. Reichhardt, J. Organometall. Chem.,369, No. 36, 335 (1989).

    Google Scholar 

  40. K. Konishi, K. Makita, T. Aida, and S. Inoue, J. Chem. Soc. Chem. Commun., No. 10, 643 (1988).

  41. S. Srivastava, J. Minore, C. K. Cheung, and W. J. Noble, J. Org. Chem.,50, No. 3, 394 (1985).

    Google Scholar 

  42. V. Z. Sharf, L. Kh. Freidlin, B. M. Savchenko, and V. N. Krutii, Izv. Akad. Nauk SSSR Ser. Khim.,8, 1894 (1976).

    Google Scholar 

  43. A. A. Balandin and A. M. Rubinshtein (eds.), Stereochemistry and Mechanisms of Organic Reactions [in Russian], Mir, Moscow (l968).

    Google Scholar 

  44. M. Shibagaki, K. Takamshi, and H. Matsuhita, Bull. Chem. Soc. Jpn.,61, 3283 (1988).

    Google Scholar 

  45. Zh. Yuskovets and M. Shimanska, Fifth International Symposium on Furan Chemistry: Abstracts of Papers, Riga (1988), p. 107.

  46. A. N. Egorochkin and G. A. Razuvaev, Usp. Khim.,61, No. 9, 1480 (1987).

    Google Scholar 

  47. S. Komiya and A. Yamamoto, J. Organometall. Chem.,46, 58 (1972).

    Google Scholar 

  48. I. S. Kolomnikov, V. P. Kukolev, V. O. Chernyshev, and M. E. Vol'pin, Izv. Akad. Nauk SSSR Ser. Khim.,3, 693 (1972)

    Google Scholar 

  49. I. S. Kolomnikov, Yu. D. Koreshkov, V. P. Kukolev, V. A. Mosin, and M. E. Vol'pin, Izv. Akad. Nauk SSSR Ser. Khim.,vn1, 175 (1973).

    Google Scholar 

  50. F. Joo and A. Be'nyei [Benyei], J. Organometall. Chem.,363, C19 (1989).

    Google Scholar 

  51. N. Tatsuya, A. Joichi, J. Yasutaka, and O. Masayo, Technol. Reports Kansai Univ.,29, 69 (1987); Ref. Zh. Khim., 19134091 (1987).

    Google Scholar 

  52. B. T. Khai and A. Arcelli, J. Organometall. Chem.,309, C63 (1986).

    Google Scholar 

  53. M. Shibagaki, K. Takahashi, H. Kuno, H. Kawakami, and H. Matsuhita, Chem. Lett., No. 10, 1633 (1988).

  54. S. Ram and L. D. Spicer, Tetrahedron Lett.,29, No. 31, 3741 (1988).

    Google Scholar 

  55. M. Shibagaki, H. Kuno, K. Takahashi, and H. Matsuhita, Bull. Soc. Chem. Jpn.,61, 4153 (1988).

    Google Scholar 

  56. E. L. Amin, G. M. Anantharamaiah, G. P. Royer, and G. E. Means, J. Org. Chem.,44, 3442 (1979).

    Google Scholar 

  57. K. Takanashi, M. Shibagaki, H. Kuno, and H. Matsuhita, Chem. Lett., No. 7, 1141 (1989).

  58. Y. Sasson and J. Blum, J. Org. Chem.,40, 1887 (1975).

    Google Scholar 

  59. V. Z. Sharf, L. Kh. Freidlin, I. S. Shekoyan, and V. N. Krutii, Izv. Akad. Nauk SSSR Ser. Khim.,4, 834 (1977).

    Google Scholar 

  60. J. Rajaram, S. Vancheesan, and J. C. Kuriacose, J. Mol. Catal.,16, 349 (1982).

    Google Scholar 

  61. R. Grigg, T. R. B. Mitchell, and S. Sutthivaiyakit, Tetrahedron,37, 4313 (1981).

    Google Scholar 

  62. V. Z. Sharf, L. K. Freidlin, I. S. Shekoyan, and V. N. Krutii, Izv. Akad. Nauk SSSR Ser. Khim.,5, 1064 (1978).

    Google Scholar 

  63. A. Camus, G. Mestroni, and G. Zassinovich, J. Mol. Catal.,6, 231 (1979).

    Google Scholar 

  64. G. Mestroni, G. Zassinovich, and A. Camus, J. Organometall. Chem.,198, 87 (l980).

    Google Scholar 

  65. G. Zassinovich, A. Camus, and G. Mestroni, J. Mol. Catal.,9; 345 (1980).

    Google Scholar 

  66. R. Spogliarich, G. Mestroni, and M. Graziani, J. Mol. Catal.,22, 309 (1984).

    Google Scholar 

  67. F. Vinzi, G. Zassinovich, and G. Mestroni, J. Mol. Catal.,18, 359 (1983).

    Google Scholar 

  68. R. Spogliarich, G. Zassinovich, G. Mestroni, and M. Graziani, J. Organometall. Chem.,179, C45 (1979).

    Google Scholar 

  69. R. Spogliarich, A. Tencich, J. Kasper, and M. Graziani, J. Organometali. Chem.,240, 453 (1982).

    Google Scholar 

  70. V. N. Krutii, S. A. Shelmakova, A. S. Gurovets, T. V. Vasina, D. B. Furman, V. Z. Sharf, and A. L. Liberman, Izv. Akad. Nauk SSSR Ser. Khim.,5, 1111 (1975).

    Google Scholar 

  71. R. Uson, L. A. Oro, R. Sariego, and Esteruelas, J. Organometall. Chem.,214, 399 (1981).

    Google Scholar 

  72. L. A. Oro, M. P. Lamata, and M. Valderrama, Transition Met. Chem.,8, 48 (1983).

    Google Scholar 

  73. G. Zassinovich and F. Grisoni, J. Organometall. Chem.,247, C24 (1983).

    Google Scholar 

  74. M. Bianchi, J. Organometall. Chem.,198 (1973).

  75. V. F. Dovganyuk, V. I. Isaeva, and V. Z. Sharf, Izv. Akad. Nauk SSSR Ser. Khim.,6, 1223 (1988).

    Google Scholar 

  76. L. A. Oro and R Sariego, React. Kinet. Catal. Lett.,21, 445 (1982).

    Google Scholar 

  77. R. L. Clowdhyry and J.-E. Béckvall, J. Chem. Soc. Chem. Commun.,27, 1063 (1991).

    Google Scholar 

  78. L. Prat, M. Rossi, M. Gargano, and N. Ravasio, Gazz. Chim. Ital.,122, 221 (1992).

    Google Scholar 

  79. R. Chauvin, J. Mol. Catal.,62, 147 (1990).

    Google Scholar 

  80. D. E. Linn, R. B. King, and A. D. King, Jr., J. Mol. Catal.,80, 165 (1993).

    Google Scholar 

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Authors
  1. Zh. Yuskovets
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  2. M. Shimanska
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Riga Institute of Organic Synthesis, Riga LV-1006, Latvia. Translated from Khimiya Geterotskilicheskikh Soedinenii, No. 4, pp. 435–449, April, 1994. Original articla submitted November 29, 1993.

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Yuskovets, Z., Shimanska, M. Catalytic intermolecular hydrogen transfer in the hydrogenation of heterocyclic aldehydes and ketones. A review. Chem Heterocycl Compd 30, 381–392 (1994). https://doi.org/10.1007/BF01169929

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