Skip to main content
Log in

Cyclopropylation of heterocyclic cores using cyclopropylboronic derivatives (microreview)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Methods for cyclopropane ring incorporation into various heterocyclic cores using cyclopropylsubstituted organoboron compounds are surveyed. In particular, Suzuki–Miyaura and Chan–Lam reactions, recent coupling processes involving organotrifluoroborates, as well as C–H activation of heterocyclic substrates are discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Miyaura, N.; Suzuki, A. Chem. Rev.1995, 95, 2457.

    Article  CAS  Google Scholar 

  2. Munir, I.; Zahoor, A. F.; Rasool, N.; Naqvi, S. A. R.; Zia, K. M.; Ahmad, R. Mol. Diversity2019, 23, 215.

    Article  CAS  Google Scholar 

  3. Sandford, C.; Aggarwal, V. K. Chem. Commun.2017, 53, 5481.

    Article  CAS  Google Scholar 

  4. Grygorenko, O. O.; Volochnyuk, D. M.; Ryabukhin, S. V.; Judd, D. B. Chem.–Eur. J.2019, 25. https://doi.org/10.1002/chem.201903232.

    Article  Google Scholar 

  5. Ma, H.-R.; Wang, X.-H.; Deng, M.-Z. Synth. Commun.1999, 29, 2477.

    Article  CAS  Google Scholar 

  6. Yao, M.-L.; Deng, M.-Z. New J. Chem.2000, 24, 425.

    Article  CAS  Google Scholar 

  7. Molander, G. A.; Gormisky, P. E. J. Org. Chem.2008, 73, 7481.

    Article  CAS  Google Scholar 

  8. Lemhadri, M.; Doucet, H.; Santelli, M. Synth. Commun.2006, 36, 121.

    Article  CAS  Google Scholar 

  9. Zhang, M.; Cui, X.; Chen, X.; Wang, L.; Li, J.; Wu, Y.; Hou, L.; Wu, Y. Tetrahedron2012, 68, 900.

    Article  CAS  Google Scholar 

  10. Deng, Q.; Shen, Y.; Zhu, H.; Tu, T. Chem. Commun.2017, 53, 13063.

    Article  CAS  Google Scholar 

  11. Chen, K.; Chen, W.; Yi, X.; Chen, W.; Liu, M.; Wu, H. Chem. Commun.2019, 55, 9287.

    Article  CAS  Google Scholar 

  12. Zhao, Y.; Snieckus, V. Adv. Synth. Catal.2014, 356, 1527.

    Article  CAS  Google Scholar 

  13. Wang, H.; Yu, S.; Qi, Z.; Li, X. Org. Lett.2015, 17, 2812.

    Article  CAS  Google Scholar 

  14. Li, G.-X.; Morales-Rivera, C. A.; Wang, Y.; Gao, F.; He, G.; Liu, P.; Chen, G. Chem. Sci.2016, 7, 6407.

    Article  CAS  Google Scholar 

  15. Xia, R.; Xie, M.-S.; Niu, H.-Y.; Qu, G.-R.; Guo, H.-M. Org. Lett.2014, 16, 444.

    Article  CAS  Google Scholar 

  16. Tsuritani, T.; Strotman, N. A.; Yamamoto, Y.; Kawasaki, M.; Yasuda, N.; Mase, T. Org. Lett.2008, 10, 1653.

    Article  CAS  Google Scholar 

  17. Bénard, S.; Neuville, L.; Zhu, J. J. Org. Chem.2008, 73, 6441.

    Article  Google Scholar 

  18. Haneda, S.; Sudo, K.; Hayashi, M. Heterocycles2011, 84, 569.

    Google Scholar 

  19. Brewer, A. C.; Hoffman, P. C.; Martinelli, J. R.; Kobierski, M. E.; Mullane, N.; Robbins, D. Org. Process Res. Dev.2019, 23, 1484.

    Article  Google Scholar 

  20. Falb, E.; Ulanenko, K.; Tor, A.; Gottesfeld, R.; Weitman, M.; Afri, M.; Gottlieb, H.; Hassner, A. Green Chem.2017, 19, 5046.

    Article  CAS  Google Scholar 

  21. Lambert, A. E.; Carrick, J. D. J. Heterocycl. Chem.2018, 55, 1232.

    Article  CAS  Google Scholar 

  22. Faldu, V. J.; Talpara, P. K.; Shah, V. H. Tetrahedron Lett.2014, 55, 1456.

    Article  CAS  Google Scholar 

  23. Hasník, Z.; Pohl, R.; Hocek, M. Synthesis2009, 1309.

  24. Savitha, B.; Sajith, A. M.; Joy, M. N.; Khader, K. K. A.; Muralidharan, A.; Padusha, M. S. A.; Bodke, Y. D. Aust. J. Chem.2016, 69, 618.

    Article  CAS  Google Scholar 

  25. Sarkar, U.; Hillebrand, R.; Johnson, K. M.; Cummings, A. H.; Phung, N. L.; Rajapakse, A.; Zhou, H.; Willis, J. R.; Barnes, C. L.; Gates, K. S. J. Heterocycl. Chem.2017, 54, 155.

    Article  CAS  Google Scholar 

  26. Noreen, M.; Rasool, N.; El Khatib, M.; Molander, G. A. J. Org. Chem.2014, 79, 7243.

    Article  CAS  Google Scholar 

  27. Cherepakha, A. Yu.; Stepannikova, K. O.; Vashchenko, B. V.; Gorichko, M. V; Tolmachev, A. A.; Grygorenko, O. O. Eur. J. Org. Chem.2018, 6682.

    Article  CAS  Google Scholar 

  28. Delaunay, T.; Es-Sayed, M.; Vors, J.-P.; Monteiro, N.; Balme, G. Eur. J. Org. Chem.2011, 3837.

    Article  CAS  Google Scholar 

  29. Hikawa, H.; Yokoyama, Y. Tetrahedron2010, 66, 9552.

    Article  CAS  Google Scholar 

  30. Strotman, N. A.; Chobanian, H. R.; He, J.; Guo, Y.; Dormer, P. G.; Jones, C. M.; Steves, J. E. J. Org. Chem.2010, 75, 1733.

    Article  CAS  Google Scholar 

  31. Ji, N.; Meredith, E.; Liu, D.; Adams, C. M.; Artman, G. D., III; Jendza, K. C.; Ma, F.; Mainolfi, N.; Powers, J. J.; Zhang, C. Tetrahedron Lett.2010, 51, 6799.

    Article  CAS  Google Scholar 

  32. Wallace, D. J.; Chen, C. Tetrahedron Lett.2002, 43, 6987.

    Article  CAS  Google Scholar 

  33. Löhr, S.; de Meijere, A. Synlett2001, 489.

  34. Duncton, M. A. J.; Singh, R. Org. Lett.2013, 15, 4284.

    Article  CAS  Google Scholar 

  35. Duncton, M. A. J.; Ayala, L.; Kaub, C.; Janagani, S.; Edwards, W. T.; Orike, N.; Ramamoorthy, K.; Kincaid, J.; Kelly, M. G. Tetrahedron Lett.2010, 51, 1009.

    Article  CAS  Google Scholar 

  36. Benoit, G.; Charette, A. B. J. Am. Chem. Soc.2017, 139, 1364.

    Article  CAS  Google Scholar 

  37. Harris, M. R.; Wisniewska, H. M.; Jiao, W.; Wang, X.; Bradow, J. N. Org. Lett.2018, 20, 2867.

    Article  CAS  Google Scholar 

  38. Harris, M. R.; Li, Q.; Lian, Y.; Xiao, J.; Londregan, A. T. Org. Lett.2017, 19, 2450.

    Article  CAS  Google Scholar 

  39. Hryshchuk, O. V.; Yurov, Y.; Tymtsunik, A. V.; Kovtunenko, V. O.; Komarov, I. V.; Grygorenko, O. O. Adv. Synth. Catal.2019, 361, 5428.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Oleksandr O. Grygorenko.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(1), 39–41

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Grygorenko, O.O., Hryshchuk, O.V. Cyclopropylation of heterocyclic cores using cyclopropylboronic derivatives (microreview). Chem Heterocycl Comp 56, 39–41 (2020). https://doi.org/10.1007/s10593-020-02619-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-020-02619-2

Navigation