Skip to main content

Potassium carbonate as a base for generation of carbanions from CH-acids in organic synthesis

Abstract

A reaction of CH-acids with electrophilic agent (Michael acceptors, alkyl and allyl halides, dihaloalkanes and -alkenes, etc.) in the presence of potassium carbonate constitutes a convenient method for the elongation of the carbon chain and provides a possibility to develop preparative methods for the preparation of both the linear and the cyclic structures.

This is a preview of subscription content, access via your institution.

References

  1. O. Khauze, Usp. Khim., 1969, 38, 1874 [Russ. Chem. Rev., 1969, 38].

    Google Scholar 

  2. Y. Zhang, W. Wang, Catal. Sci. Technol., 2012, 2, 42.

    Article  CAS  Google Scholar 

  3. R. Tan, F. S. N. Chiu, A. Hadzovic, D. Song, Organometallics, 2012, 31, 2184.

    Article  CAS  Google Scholar 

  4. Y.-R. Yang, W.-D. Z. Li, J. Org. Chem., 2005, 70, 8224.

    Article  CAS  Google Scholar 

  5. W. Weber, G. Gokel, Phase Transfer Catalysis in Organic Synthesis, Springer-Verlag, Berlin—Heidelberg—New York, 1977.

    Book  Google Scholar 

  6. M. Makosza, Russ. Chem. Rev., 1977, 46, 1151.

    Article  Google Scholar 

  7. M. Fedorinski, K. Wojciechowski, Z. Matacz, M. Makosza, J. Org. Chem., 1978, 43, 4682.

    Article  Google Scholar 

  8. N. M. Morlyan, D. S. Khachatryan, Sh. O. Badanyan, Arm. Khim. Zh. [Arm. Chem. J.], 1980, 33, 733 (in Russian).

    CAS  Google Scholar 

  9. K. D. Deshayes, in Encyclopedia of Reagents for Organic Synthesis, J. Wiley and Sons, New York, 1999, 6, 4203.

    Google Scholar 

  10. L. A. Paquette, in Encyclopedia of Reagents for Organic Synthesis, J. Wiley and Sons, New York, 1999, 6, 4205.

    Google Scholar 

  11. H. S. P. Rao, S. Jothilingam, J. Chem. Sci., 2005, 117, 323.

    Article  CAS  Google Scholar 

  12. R. Mondal, A. K. Mallik, Org. Prep. Proc. Int., 2014, 46, 391.

    Article  CAS  Google Scholar 

  13. D. Y. Kim, S. C. Huh, S. M. Kim, Tetrahedron Lett., 2001, 42, 6299.

    Article  CAS  Google Scholar 

  14. R. T. Dere, R. R. Pal, P. S. Patil, M. M. Salunkhe, Tetrahedron Lett., 2003, 44, 5351.

    Article  CAS  Google Scholar 

  15. A. s. 417410 SSSR; Byul. isobret. [Invention Bull.], 1974, 8 (in Russian).

  16. N. M. Morlyan, D. S. Khachatryan, Sh. O. Badanyan, Arm. Khim. Zh. [Arm. Chem. J.], 1978, 31, 866 (in Russian).

    CAS  Google Scholar 

  17. D. S. Khachatryan, N. M. Morlyan, R. G. Mirzoyan, Sh. O. Badanyan, Arm. Khim. Zh. [Arm. Chem. J.], 1980, 33, 850 (in Russian).

    CAS  Google Scholar 

  18. D. S. Khachatryan, N. M. Morlyan, P. V. Mkhitaryan, R. G. Mirzoyan, Sh. O. Badanyan, Arm. Khim. Zh. [Arm. Chem. J.], 1981, 34, 480 (in Russian).

    CAS  Google Scholar 

  19. D. S. Khachatryan, N. M. Morlyan, Sh. O. Badanyan, Arm. Khim. Zh. [Arm. Chem. J.], 1981, 34, 665 (in Russian).

    CAS  Google Scholar 

  20. D. S. Khachatryan, N. M. Morlyan, R. G. Mirzoyan, Sh. O. Badanyan, Arm. Khim. Zh. [Arm. Chem. J.], 1981, 34, 672 (in Russian).

    CAS  Google Scholar 

  21. N. Race, J. Bower, Org. Lett., 2013, 15, 4616.

    Article  CAS  Google Scholar 

  22. E. D. Bergmann, D. Ginsburg, R. Pappo, in Organic Reactions, Vol. 10, Ed. R. Adams, J. Wiley and Sons, New York, 1959.

  23. A. A. Akhrem, Yu. A. Titov, Polnyi sintez steroidov, Nauka, Moscow, 1967, 320 pp. (in Russian).

    Google Scholar 

  24. D. S. Khachatryan, A. A. Vardapetyan, N. M. Morlyan, A. L. Razinov, K. R. Matevosyan, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 385 [Izv. Akad. Nauk, Ser. Khim., 2015, 385].

    Article  CAS  Google Scholar 

  25. A. s. 1704446 SSSR; Byul. Izobret. [Invention Bull.], 2000, 9 (in Russian).

  26. D. S. Khachatryan, A. A. Vardapetyan, V. N. Tkachenko, N. M. Morlyan, Tez. dokl. III Vsesoyuzn. soveshchaniya po khimicheskim reaktivam [Abstracts of All-Soviet Union Conference on Chemical Reactants], Ashkhabad, 1989, P 107 (in Russian).

    Google Scholar 

  27. V. I. Zelenov, A. V. Chernova, L. I. Lysenko, Russ. J. Gen. Chem. (Engl. Transl.), 2009, 79, 142 [Zh. Obshch. Khim., 2009, 79, 146].

    Article  CAS  Google Scholar 

  28. L. A. Yanovskaya, V. A. Dombrovskii, A. Kh. Khusid, Tsiklopropany s funktsionalńymi gruppami [Cyclopropanes with Functional Groups], Nauka, Moscow, 1980, 223 pp. (in Russian).

    Google Scholar 

  29. V. P. Sheverdov, Dr. Sci. Thesis (Pharm.), Perm’ State Pharmeceutical Academy, Perm’, 2009, 261 pp. (in Russian).

    Google Scholar 

  30. N. I. Shtemenko, G. V. Kryshtal, L. A. Yanovskaya, Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 29, 2420 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1980, 29].

    Google Scholar 

  31. G. V. Kryshtal, N. I. Shtemenko, L. A. Yanovskaya, Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 29, 2831 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1980, 29].

    Google Scholar 

  32. A. A. Vardapetyan, D. S. Khachatryan, G. A. Panosyan, N. M. Morlyan, Zh. Org. Khim., 1986, 22, 2262 [J. Org. Chem. USSR (Engl. Transl.), 1986, 22].

    CAS  Google Scholar 

  33. Y. Kawakami, T. Tsuruta, Bull. Chem. Soc. Jpn, 1973, 46, 2262.

    Article  CAS  Google Scholar 

  34. U. Scmidt, R. Schroer, A. Hocrainer, Liebigs Ann. Chem., 1970, 733, 180.

    Article  Google Scholar 

  35. H. Weitkamp, F. Korte, Tetrahedron, 1964, 20, 2125.

    Article  CAS  Google Scholar 

  36. M. Barreau, M. Bost, M. Julia, J.-Y. Lallemand, Tetrahedron Lett., 1975, 16, 3465.

    Article  Google Scholar 

  37. M. J. Mitton-Fry, A. J. Cullen, T. Sammakia, Angew. Chem., Int. Ed. Engl., 2007, 46, 1066.

    Article  CAS  Google Scholar 

  38. K. Harada, H. Ito, H. Hioki, Y. Fukuyama, Tetrahedron Lett., 2007, 48, 6105.

    Article  CAS  Google Scholar 

  39. D. Garayalde, E. Gómez-Bengoa, X. Huang, A. Goeke, C. Nevado, J. Am. Chem. Soc., 2010, 132, 4720.

    Article  CAS  Google Scholar 

  40. A. Fürstner, L. C. Bouchez, J.-A. Funel, V. Liepins, F.-H. Porée, R. Gilmour, F. Beaufils, D. Laurich, M. Tamiya, Angew. Chem., Int. Ed. Engl., 2007, 46, 9265.

    Article  Google Scholar 

  41. B. Rabin, G. Dhananjaya, S. N. Singh, R. Kumar, K. Mukkanti, M. Pal, Tetrahedron, 2009, 65, 1300.

    Article  Google Scholar 

  42. F. Felluga, G. Pitacco, V. Ennio, C. Venneri, Tetrahedron Asymmetry, 2008, 19, 945.

    Article  CAS  Google Scholar 

  43. T. Yoshida, M. Murai, M. Abe, N. Ichimaru, T. Harada, T. Nishioka, H. Miyoshi, Biochemistry, 2007, 46, 10365.

    Article  CAS  Google Scholar 

  44. D. Fischer, A. Barakat, Z.-Q. Xin, M. E. Weiss, R. Peters, Chem. Eur. J., 2009, 15, 8722.

    Article  CAS  Google Scholar 

  45. S. Crosby, R. Sessions, C. Willis, Synlett, 2010, 4, 539.

    Google Scholar 

  46. K. Ando, K. Yamada, Green Chem., 2011, 13, 1143.

    Article  CAS  Google Scholar 

  47. W. Shearouse, C. Korte, J. Mack, Green Chem., 2011, 13, 598.

    Article  CAS  Google Scholar 

  48. Z. Liu, Y. Gong, H. Byun, R. Bittman, N. J. Chem., 2010, 34, 470.

    Article  CAS  Google Scholar 

  49. Z. Wanke, Huaxue Shiji, 2012, 34, 565.

    Google Scholar 

  50. B.-C. Hong, P.-Y. Chen, P. Kotame, P.-Y. Lu, G.-H. Lee, J.-H. Liao, Chem. Commun., 2012, 48, 7790.

    Article  CAS  Google Scholar 

  51. L. A. Yanovskaya, S. S. Yufit, Organicheskii sintez v dvukhfaznykh sistemakh [Organic Synthesis in Two-Phase Systems], Khimiya, Moscow, 1982, 121 (in Russian).

  52. L. A. Yanovskaya, Ross. Khim. Zh., 1986, 31, 158 [Mendeleev Chem. J. (Engl. Transl.), 1986, 31].

    CAS  Google Scholar 

  53. G. V. Kryshtal, V. V. Kul’ganek, V. F. Kucherov, L. A. Yanovskaya, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1978, 27, 2508.

    Article  Google Scholar 

  54. G. V. Kryshtal, V. V. Kulganek, V. P. Kucherov, L. A. Yanovskaya, Synthesis, 1979, 2, 107.

    Article  Google Scholar 

  55. L. A. Yanovskaya, G. V. Kryshtal, V. V. Kul’ganek, Russ. Chem. Rev., 1984, 53, 744.

  56. N. I. Shtemenko, G. V. Kryshtal, L. A. Yanovskaya, Izv. Akad. Nauk SSSR, Ser. Khim., 1981, 30, 445 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1981, 30].

    Google Scholar 

  57. Z. Arnold, V. Kral, G. V. Kryshtal, L. A. Yanovskaya, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1983, 32, 1954 [Izv. Akad. Nauk SSSR, Ser. Khim., 1983, 32, 2162].

    Article  Google Scholar 

  58. Z. Arnold, V. Kral, G. V. Kryshtal, L. A. Yanovskaya, Synthesis, 1984, 11, 974.

    Article  Google Scholar 

  59. G. V. Kryshtal, Tez. dokl. IV Vsesoyuzn. simpoziuma po organicheskomu sintezu [Abstracts of IV All-Soviet Union Symposium on Organic Synthesis], Moscow, 1984, P-37 (in Russian).

    Google Scholar 

  60. G. V. Kryshtal, K. Ya. Burshtein, V. V. Kul’ganek, L. A. Yanovskaya, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1984, 33, 2328 [Izv. Akad. Nauk SSSR, Ser. Khim., 1984, 33, 2541].

    Article  Google Scholar 

  61. G. V. Kryshtal, G. M. Zhdankina, I. V. Astakhova, S. G. Zlotin, Russ. Chem. Bull. (Int. Ed.), 2004, 53, 647 [Izv. Akad. Nauk, Ser. Khim., 2004, 618].

    Article  CAS  Google Scholar 

  62. S. G. Zlotin, G. V. Kryshtal, G. M. Zhdankina, A. V. Ignatenko, Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin, Zh. Org. Khim., 2010, 46, 479 [Russ. J. Org. Chem. (Engl. Transl.), 2010, 46].

    Google Scholar 

  63. E. A. Parfenov, A. R. Becker, G. F. Kostereva, Zh. Org. Khim., 1981, 17, 1591 [J. Org. Chem. USSR (Engl. Transl.), 1981, 17].

    CAS  Google Scholar 

  64. S. G. Zlotin, A. V. Bogolyubov, G. V. Kryshtal, G. M. Zhdankina, M. I. Struchkova, V. A. Tartakovsky, Synthesis, 2006, 22, 3849.

    Article  Google Scholar 

  65. F. Barbot, D. Mesnard, L. Miginiac, Org. Prep. Proced. Int., 1978, 10, 261.

    Article  CAS  Google Scholar 

  66. G. M. Makaryan, M. S. Sargsyan, Sh. O. Badanyan, Arm. Khim. Zh. [Arm. Chem. J.] 1979, 32, 217 (in Russian).

    CAS  Google Scholar 

  67. C. S. Yufit, Mekhanizm mezhfaznogo kataliza [Mechanism of Phase-Transfer Catalysis], Nauka, Moscow, 1984, 263 pp. (in Russian).

  68. S. S. Yufit, I. A. Esikova, Dokl. Akad. Nauk SSSR, 1982, 265, 358 [Dokl. Chem. (Engl. Transl.), 1982, 265].

    CAS  Google Scholar 

  69. S. S. Yufit, I. A. Esikova, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1983, 32, 36 [Izv. Akad. Nauk SSSR, Ser. Khim., 1983, 32, 47].

    Article  Google Scholar 

  70. S. S. Yufit, Ross. Khim. Zh., 1986, 31, 134 [Mendeleev Chem. J. (Engl. Transl.), 1986, 31].

    CAS  Google Scholar 

  71. S. Kotha, S. Brahmachary, Bioorg. Med. Chem. Lett., 1997, 7, 2719.

    Article  CAS  Google Scholar 

  72. J. Lohier, K. Wright, C. Peggion, F. Formaggio, C. Toniolo, M. Wakselman, J. Mazaleyrat, Tetrahedron, 2006, 62, 6203.

    Article  CAS  Google Scholar 

  73. S. Kotha, E. Brahmachary, A. Kuki, K. Lang, D. Anglos, B. Singaram, W. Chrisman, Tetrahedron Lett., 1997, 38, 9031.

    Article  CAS  Google Scholar 

  74. N. N. Sukhanov, L. I. Trappel’, V. P. Chetverikov, L. A. Yanovskaya, Zh. Org. Khim., 1985, 21, 2503 [J. Org. Chem. USSR (Engl. Transl.), 1985, 21].

    CAS  Google Scholar 

  75. G. V. Kryshtal, G. M. Zhdankina, S. G. Zlotin, Mendeleev Commun., 2002, 12, 57

    Article  Google Scholar 

  76. G. V. Kryshtal, G. M. Zhdankina, S. G. Zlotin, Russ. Chem. Bull. (Int. Ed.), 2004, 53, 652 [Izv. Akad. Nauk, Ser. Khim., 2004, 622].

    Article  CAS  Google Scholar 

  77. D. A. White, Synth. Commun., 1977, 7, 559.

    Article  CAS  Google Scholar 

  78. JP Pat. 78149953; Chem. Abstrs, 1979, 90, 151660z.

  79. HU Pat. 188822; Chem. Abstrs, 1985, 102, 131581n.

  80. CZ Pat. 208559; Chem. Abstrs, 1980, 101, 54923a.

  81. H. C. Zefirov, T. S. Kuznetsova, S. I. Kozhushkov, L. S. Surmin, Zh. Org. Khim., 1983, 19, 541 [J. Org. Chem. USSR (Engl. Transl.), 1983, 19].

    CAS  Google Scholar 

  82. N. S. Zefirov, T. S. Kuznetsova, S. I. Kozhushkov, Zh. Org. Khim., 1983, 19, 1599 [J. Org. Chem. USSR (Engl. Transl.), 1983, 19].

    CAS  Google Scholar 

  83. N. S. Sadykhov, N. S. Zefirov, S. T. Akhmedov, V. M. Ismailov, Abstr. of VI Int. Conf. on Organic Synthesis, Moscow, 1986, P-49.

    Google Scholar 

  84. J. Moubarak, R. Vessiere, Synthesis, 1980, 52.

    Google Scholar 

  85. Y. Sun, G. Yang, Y. Shen, Z. Hua, Z. Chai, Tetrahedron, 2013, 69, 2733.

    Article  CAS  Google Scholar 

  86. G. V. Kryshtal, G. M. Zhdankina, A. S. Shashkov, S. G. Zlotin, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 2279 [Izv. Akad. Nauk, Ser. Khim., 2011, 2237].

    Article  CAS  Google Scholar 

  87. G. V. Kryshtal, G. M. Zhdankina, S. G. Zlotin, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 2286 [Izv. Akad. Nauk, Ser. Khim., 2011, 2244].

    Article  CAS  Google Scholar 

  88. K. V. Vatsuro, G. L. Mishchenko, Imennye reaktsii v organicheskoi khimii [Named Reactions in Organic Chemistry], Khimiya, Moscow, 1976, 194 pp. (in Russian).

  89. J. Nickel, Chem. Ber., 1958, 91, 553.

    Article  Google Scholar 

  90. A. A. Vardapetyan, D. S. Khachatryan, N. M. Morlyan, Zh. Org. Khim., 1988, 24, 1374 [J. Org. Chem. USSR (Engl. Transl.), 1988, 24].

    CAS  Google Scholar 

  91. A. A. Vardapetyan, D. S. Khachatryan, G. A. Panosyan, N. M. Morlyan, Zh. Org. Khim., 1986, 22, 2266 [J. Org. Chem. USSR (Engl. Transl.), 1986, 22].

    CAS  Google Scholar 

  92. A. A. Vardapetyan, D. S. Khachatryan, N. M. Morlyan, Sh. O. Badanyan, Tez. dokl. IV Vsesoyuzn. simpoziuma po organicheskomu sintezu [Abstracts of IV All-Soviet Union Symposium on Organic Synthesis], Moscow, 1984, 61 (in Russian).

  93. R. W. Kierstead, R. P. Linstead, B. C. L. Weedon, J. Chem. Soc., 1952, 5, 3610.

    Article  Google Scholar 

  94. R. W. Kierstead, R. P. Linstead, B. C. L. Weedon, J. Am. Chem. Soc., 1953, 75, 1799.

    Article  Google Scholar 

  95. M. G. Vinogradov, M. S. Pogosyan, A. Ya. Shteinshneider, G. I. Nikishin, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1981, 30, 1703 [Izv. Akad. Nauk SSSR, Ser. Khim., 1981, 2077].

    Article  Google Scholar 

  96. D. S. Khachatryan, A. A. Vardapetyan, G. A. Panosyan, R. G. Mirzoyan, N. M. Morlyan, Zh. Org. Khim., 1990, 26, 2092 [J. Org. Chem. USSR (Engl. Transl.), 1990, 26].

    CAS  Google Scholar 

  97. D. S. Khachatryan, A. L. Razinov, A. V. Kolotaev, S. K. Belus’, K. R. Matevosyan, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 395 [Izv. Akad. Nauk, Ser. Khim., 2015, 395].

    Article  CAS  Google Scholar 

  98. B. A. Trofimova, A. G. Mal’kina, V. V. Nosyreva, O. A. Shemyakina, A. P. Borisova, L. I. Larina, O. N. Kazheva, G. G. Alexandrov, O. A. Dyachenko, Tetrahedron, 2010, 66, 1699.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to D. S. Khachatryan.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0014—0028, January, 2016.

Rights and permissions

Reprints and Permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khachatryan, D.S., Matevosyan, K.R. Potassium carbonate as a base for generation of carbanions from CH-acids in organic synthesis. Russ Chem Bull 65, 14–28 (2016). https://doi.org/10.1007/s11172-016-1260-z

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-016-1260-z

Keywords