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N-(Alkoxy)- and N-(acyloxy)phthalimides in organic synthesis: free radical synthetic approaches and applications (microreview)

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Chemistry of Heterocyclic Compounds Aims and scope

The microreview covers selected examples of the free radical cross-dehydrogenative C–O coupling of various CH reagents with N-hydroxyphthalimide leading to N-(alkoxy)- and N-(acyloxy)phthalimides. Synthetic applications of the latter associated with the cleavage of N–O bond leading to the O-, N- and C-centered free radicals are also reviewed.

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References

  1. Krylov, I. B.; Vil’, V. A.; Terent’ev, A. O. Beilstein J. Org. Chem.2015, 11, 92.

  2. Terent'ev, A. O.; Krylov, I. B.; Sharipov, M. Y.; Kazanskaya, Z. M.; Nikishin, G. I. Tetrahedron2012, 68, 10263.

    Article  CAS  Google Scholar 

  3. Lee, J. M.; Park, E. J.; Cho, S. H.; Chang, S. J. Am. Chem. Soc.2008, 130, 7824.

    Article  CAS  Google Scholar 

  4. Krylov, I. B.; Kompanets, M. O.; Novikova, K. V.; Opeida, I. O.; Kushch, O. V.; Shelimov, B. N.; Nikishin, G. I.; Levitsky, D. O.; Terent'ev, A. O. J. Phys. Chem. A2016, 120, 68.

    Article  CAS  Google Scholar 

  5. Mahajan, J. P.; Mhaske, S. B. Org. Lett.2017, 19, 2774.

    Article  CAS  Google Scholar 

  6. Qian, P.-C.; Liu, Y.; Song, R.-J.; Hu, M.; Yang, X.-H.; Xiang, J.-N.; Li, J.-H. Eur. J. Org. Chem.2015, 1680.

    Article  CAS  Google Scholar 

  7. Lv, Y.; Sun, K.; Wang, T.; Li, G.; Pu, W.; Chai, N.; Shen, H.; Wu, Y. RSC Adv.2015, 5, 72142.

    Article  CAS  Google Scholar 

  8. Dian, L.; Wang, S.; Zhang-Negrerie, D.; Du, Y. Adv. Synth. Catal.2015, 357, 3836.

    Article  CAS  Google Scholar 

  9. Jiang, H.; Tang, X.; Liu, S.; Wang, L.; Shen, H.; Yang, J.; Wang, H.; Gui, Q.-W. Org. Biomol. Chem.2019, 17, 10223.

    Article  CAS  Google Scholar 

  10. Xu, X.; Sun, J.; Lin, Y.; Cheng, J.; Li, P.; Yan, Y.; Shuai, Q.; Xie, Y. Org. Biomol. Chem.2017, 15, 9875.

    Article  CAS  Google Scholar 

  11. Guo, Z.; Jin, C.; Zhou, J.; Su, W. RSC Adv.2016, 6, 79016.

    Article  CAS  Google Scholar 

  12. Terent'ev, A. O.; Krylov, I. B.; Timofeev, V. P.; Starikova, Z. A.; Merkulova, V. M.; Ilovaisky, A. I.; Nikishin, G. I. Adv. Synth. Catal.2013, 355, 2375.

    Article  CAS  Google Scholar 

  13. Siddaraju, Y.; Prabhu, K. R. Org. Biomol. Chem.2015, 13, 11651.

    Article  CAS  Google Scholar 

  14. Xu, X.; Sun, J.; Lin, Y.; Cheng, J.; Li, P.; Jiang, X.; Bai, R.; Xie, Y. Eur. J. Org. Chem.2017, 7160.

  15. Murarka, S. Adv. Synth. Catal.2018, 360, 1735.

    Article  CAS  Google Scholar 

  16. Li, P.; Sun, J.; Xu, X.; Mi, Z.; Lin, Y.; Cheng, J.; Bai, R.; Xie, Y. Tetrahedron Lett.2018, 59, 2640.

    Article  CAS  Google Scholar 

  17. Xu, X.; Li, P.; Huang, Y.; Tong, C.; Yan, Y.; Xie, Y. Tetrahedron Lett.2017, 58, 1742.

    Article  CAS  Google Scholar 

  18. Dinda, M.; Bose, C.; Ghosh, T.; Maity, S. RSC Adv.2015, 5, 44928.

    Article  CAS  Google Scholar 

  19. Feizpour, F.; Jafarpour, M.; Rezaeifard, A. New J. Chem.2018, 42, 807.

    CAS  Google Scholar 

  20. Krylov, I. B.; Paveliev, S. A.; Shelimov, B. N.; Lokshin, B. V.; Garbuzova, I. A.; Tafeenko, V. A.; Chernyshev, V. V.; Budnikov, A. S.; Nikishin, G. I.; Terent'ev, A. O. Org. Chem. Front.2017, 4, 1947.

    Article  CAS  Google Scholar 

  21. Syroeshkin, M. A.; Krylov, I. B.; Hughes, A. M.; Alabugin, I. V.; Nasybullina, D. V.; Sharipov, M. Yu.; Gultyai, V. P.; Terent'ev, A. O. J. Phys. Org. Chem.2017, 30, e3744.

    Article  Google Scholar 

  22. Liu, Y.; Xue, L.; Shi, B.; Bu, F.; Wang, D.; Lu, L.; Shi, R.; Lei, A. Chem. Commun.2019, 55, 14922

    Article  CAS  Google Scholar 

  23. Zhang, Y.; Liu, H.; Tang, L.; Tang, H.-J.; Wang, L.; Zhu, C.; Feng, C. J. Am. Chem. Soc.2018, 140, 10695.

    Article  CAS  Google Scholar 

  24. Deng, Y.; Nguyen, M. D.; Zou, Y.; Houk, K. N.; Smith, A. B., III Org. Lett.2019, 21, 1708.

    Article  CAS  Google Scholar 

  25. Allen, L. J.; Cabrera, P. J.; Lee, M.; Sanford, M. S. J. Am. Chem. Soc.2014, 136, 5607.

    Article  CAS  Google Scholar 

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Acknowledgement

This work is supported by a grant from the President of the Russian Federation for state support of young Russian scientists (grant MK-3613.2019.3).

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Correspondence to Igor B. Krylov.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(1), 36–38

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Budnikov, A.S., Krylov, I.B. N-(Alkoxy)- and N-(acyloxy)phthalimides in organic synthesis: free radical synthetic approaches and applications (microreview). Chem Heterocycl Comp 56, 36–38 (2020). https://doi.org/10.1007/s10593-020-02618-3

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  • DOI: https://doi.org/10.1007/s10593-020-02618-3

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