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Chemoselective cross-coupling of terminal propargylamines with (het)aroyl chlorides: synthesis of β-aminoacetylenic ketones bearing aromatic and heteroaromatic substituents

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Abstract

Terminal secondary 4-chlorophenyl propargylamines, synthesized by addition of acetylene to N-(4-chlorophenyl)ketimines (ButOK, DMSO, 20–25 °C) in 76–93% yields, in the presence of the PdCl2/CuI/Ph3P catalytic system cross-coupled with aromatic and heteroaromatic acyl chlorides at the terminal carbon atom of the acetylenic unit to give chemoselectively β-[(4-chlorophenyl)amino]acetylenic ketones in 80–85% yields. Under these conditions, neither expected acylation of the NH-bond nor possible intramolecular cross-coupling involving carbon atom of 4-chlorophenylamine substituent occurred.

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References

  1. C. Nájera, L. K. Sydnes, M. Yus, Chem. Rev., 2019, 119, 11110.

    Article  Google Scholar 

  2. F. Diederich, P. J. Stang, R.R. Tykwinski, Acetylene Chemistry: Chemistry, Biology and Material Science, Wiley-VCH, Weinheim, Germany, 2005, 528 pp.

    Google Scholar 

  3. G. Zeni, D. S. Lüdtke, C. W. Nogueira, R. B. Panatieri, A. L. Braga, C. C. Silveira, H. A. Stefani, Tetrahedron Lett., 2001, 42, 8927.

    Article  CAS  Google Scholar 

  4. D. Li, J. Yang, B. Liu, J. Gong, Z. Yang, Org. Lett., 2021, 23, 4532.

    Article  CAS  Google Scholar 

  5. L. N. Sobenina, D. N. Tomilin, B. A. Trofimov, Russ. Chem. Rev., 2014, 83, 475.

    Article  Google Scholar 

  6. L. N. Sobenina, B. A. Trofimov, Molecules, 2020, 25, 2490.

    Article  CAS  Google Scholar 

  7. L. N. Sobenina, E. F. Sagitova, O. V. Petrova, B. A. Trofimov, Mendeleev Commun., 2021, 31, 573.

    Article  CAS  Google Scholar 

  8. L. N. Sobenina, D. N. Tomilin, M. D. Gotsko, I. A. Ushakov, B. A. Trofimov, Tetrahedron, 2018, 74, 1565; DOI: https://doi.org/10.1016/j.tet.2018.02.024.

    Article  CAS  Google Scholar 

  9. A. Yu. Mitrofanov, I. P. Beletskaya, Mendeleev Commun., 2021, 31, 536; DOI: https://doi.org/10.1016/j.mencom.2021.07.033.

    Article  CAS  Google Scholar 

  10. J. Tohda, K. Sonogashira, N. Hagihara, Synthesis, 1977, 777; DOI: https://doi.org/10.1055/s-1977-24574.

  11. A. S. Zanina, S. I. Shergina, I. E. Sokolov, I. L. Kotlyarevskii, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1981, 30, 918; DOI: https://doi.org/10.1007/BF00955319.

    Article  Google Scholar 

  12. K. Oshimoto, H. Tsuji, M. Kawatsura, Org. Biomol. Chem., 2019, 17, 4225; DOI: https://doi.org/10.1039/C9OB00572B.

    Article  CAS  Google Scholar 

  13. I. Karpavičienė, M. Jonušis, K. Leduskrasts, I. Misiūnaitė, E. Suna, I. Čikotienė, Dyes Pigm., 2019, 170, 107646; DOI: https://doi.org/10.1016/j.dyepig.2019.107646.

    Article  Google Scholar 

  14. R. E. Whittaker, A. Dermenci, G. Dong, Synthesis, 2016, 48, 161; DOI: https://doi.org/10.1055/s-0035-1560515.

    CAS  Google Scholar 

  15. D. Oguro, H. Watanabe, Y. Okubo, JP Pat. 2005/145953.

  16. G. Cahiez, O. Gager, A. Moyeux, B. Laboue-Bertrand, Synthesis, 2010, 4213.

  17. I. A. Bidusenko, E. Yu. Schmidt, I. A. Ushakov, B. A. Trofimov, Eur. J. Org. Chem., 2018, 4845.

  18. E. Yu. Schmidt, I. A. Bidusenko, N. I. Protsuk, Y. V. Demyanov, I. A. Ushakov, B. A. Trofimov, Eur. J. Org. Chem., 2019, 5875.

  19. E. Yu. Schmidt, I. A. Bidusenko, N. I. Protsuk, Y. V. Demyanov, I. A. Ushakov, A. V. Vashchenko, B. A. Trofimov, J. Org. Chem., 2020, 85, 3417.

    Article  Google Scholar 

  20. A. V. Vasil’ev, A. P. Rudenko, E. V. Grinenko, Russ. J. Org. Chem., 2000, 36, 1157.

    Google Scholar 

  21. A. M. Manzo, A. Perboni, G. Broggini, M. Rigamonti, Synthesis, 2011, 127.

  22. B. Rajagopal, C.-H. Chou, C.-C. Chung, P.-C. Lin, Org. Lett., 2014, 16, 3752.

    Article  CAS  Google Scholar 

  23. S. Das, A. Azim, S. K. Hota, S. P. Panda, S. Murarka, S. De Sarkar, Chem. Commun., 2021, 57, 13130.

    Article  CAS  Google Scholar 

  24. X. Zhu, R. Li, H. Yao, A. Lin, Org. Lett., 2021, 23, 4630.

    Article  CAS  Google Scholar 

  25. M. Lemhadri, H. Doucet, M. Santelli, Synthesis, 2005, 1359.

  26. X. Pu, H. Li, T. J. Colacot, J. Org. Chem., 2013, 78, 568.

    Article  CAS  Google Scholar 

  27. I. R. Ramazanov, R. N. Kadikova, Z. R. Saitova, U. M. Dzhemilev, Russ. Chem. Bull., 2020, 69, 61.

    Article  CAS  Google Scholar 

  28. M. S. Kobzev, A. A. Titov, A. V. Varlamov, Russ. Chem. Bull., 2021, 70, 1213.

    Article  CAS  Google Scholar 

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Funding

This work was financially supported by the Russian Science Foundation (Project No. 19-13-00052 (synthesis of propargylamines, aza-Favorskii reaction) and No. 18-73-10080P (acylation of propagylamines)) using the equipment of Baikal Analytical Joint Use Center of the Siberian Branch of the Russian Academy of Sciences.

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Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russia

    P. A. Volkov, K. O. Khrapova, I. A. Bidusenko, A. A. Telezhkin, E. Yu. Schmidt, A. I. Albanov & B. A. Trofimov

Authors
  1. P. A. Volkov
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  2. K. O. Khrapova
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  3. I. A. Bidusenko
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  4. A. A. Telezhkin
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  5. E. Yu. Schmidt
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  6. A. I. Albanov
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  7. B. A. Trofimov
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Corresponding author

Correspondence to B. A. Trofimov.

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Dedicated to Academician of the Russian Academy of Sciences V. I. Ovcharenko on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1514–1518, July, 2022.

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Volkov, P.A., Khrapova, K.O., Bidusenko, I.A. et al. Chemoselective cross-coupling of terminal propargylamines with (het)aroyl chlorides: synthesis of β-aminoacetylenic ketones bearing aromatic and heteroaromatic substituents. Russ Chem Bull 71, 1514–1518 (2022). https://doi.org/10.1007/s11172-022-3558-3

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  • DOI: https://doi.org/10.1007/s11172-022-3558-3

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