Metal-free reductive c-c-coupling between arylboronic acids and 2-(5-iodo-1,2,3-triazolyl)phenols

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription or Fee Access

Abstract

A novel approach to 2-(1-arylalkyl)benzoxazoles via a reaction of arylboronic acids with 2-(5-iodo-1,2,3-triazolyl)phenols has been developed. The key intermediates of the proposed cascade transformation are 2-(1-diazoalkyl)benzoxazoles, entering reductive C-C-coupling with boronic acids. The reaction proceeds under transition-metal-free conditions and affords target compounds in yields up to 67%.

About the authors

A. G. Gevondian

M.V. Lomonosov Moscow State University

Y. N. Kotovshchikov

M.V. Lomonosov Moscow State University

Email: kotovshchikov@org.chem.msu.ru

G. V. Latyshev

M.V. Lomonosov Moscow State University

N. V. Lukashev

M.V. Lomonosov Moscow State University

I. P. Beletskaya

M.V. Lomonosov Moscow State University

References

  1. Bakulev V., Dehaen W., Beryozkina T. Top. Heterocycl. Chem. 2015, 40, 1-49. doi: 10.1007/7081_2014_131
  2. Akter M., Rupa K., Anbarasan P. Chem. Rev. 2022, 122, 13108-13205. doi.org/10.1021/acs.chemrev.1c00991
  3. Jiang Y., Sun R., Tang X.-Y., Shi M. Chem. Eur. J. 2016, 22, 17910-17924. doi: 10.1002/chem.201601703
  4. Wang Y., Lei X., Tang Y. Synlett. 2015, 26, 2051-2059. doi: 10.1055/s-0034-1380444
  5. Li Y., Yang H., Zhai H. Chem. Eur. J. 2018, 24, 12757-12766. doi: 10.1002/chem.201800689
  6. Davies H.M.L., Alford J.S. Chem. Soc. Rev. 2014, 43, 5151-5162. doi: 10.1039/C4CS00072B
  7. Pal K., Volla C.M.R. Chem. Rec. 2021, 21, 4032-4058. doi: 10.1002/tcr.202100238
  8. Motornov V., Beier P. J. Org. Chem. 2018, 83, 15195-15201. doi: 10.1021/acs.joc.8b02472
  9. Motornov V., Markos A., Beier P. Chem. Commun. 2018, 54, 3258-3261. doi: 10.1039/C8CC01446A
  10. Tichý D., Koštál V., Motornov V., Klimánková I., Beier P. J. Org. Chem. 2020, 85, 11482-11489. doi: 10.1021/acs.joc.0c01610
  11. Yadagiri D., Rivas M., Gevorgyan V. J. Org. Chem. 2020, 85, 11030-11046. doi: 10.1021/acs.joc.0c01652
  12. Filippov I.P., Titov G.D., Rostovskii N.V. Synthesis. 2020, 52, 3564-3576. doi: 10.1055/s-0040-1707254
  13. Котовщиков Ю.Н., Волошкин В.А., Латышев Г.В., Лукашев Н.В., Белецкая И.П. ЖОрХ. 2021, 57, 1084-1119.
  14. Kotovshchikov Y.N., Voloshkin V.A., Latyshev G.V., Lukashev N.V., Beletskaya I.P. Russ. J. Org. Chem. 2021, 57, 1212-1244. doi: 10.1134/S1070428021080029
  15. Shen R., Yin K., Yu M., Li X. Asian J. Org. Chem. 2023, 12, e202200631. doi: 10.1002/ajoc.202200631
  16. Tatevosyan S.S., Kotovshchikov Y.N., Latyshev G.V., Erzunov D.A., Sokolova D.V., Beletskaya I.P., Lukashev N.V. J. Org. Chem. 2020, 85, 7863-7876. doi: 10.1021/acs.joc.0c00520
  17. Voloshkin V.A., Kotovshchikov Y.N., Latyshev G.V., Lukashev N.V., Beletskaya I.P. J. Org. Chem. 2022, 87, 7064-7075. doi: 10.1021/acs.joc.2c00235
  18. Tatevosyan S.S., Kotovshchikov Y.N., Latyshev G.V., Lukashev N.V., Beletskaya I.P. Synthesis. 2022, 54, 369-377. doi: 10.1055/a-1623-2333
  19. Kotovshchikov Y.N., Latyshev G.V., Navasardyan M.A., Erzunov D.A., Beletskaya I.P., Lukashev N.V. Org. Lett. 2018, 20, 4467-4470. doi: 10.1021/acs.orglett.8b01755
  20. Kotovshchikov Y.N., Latyshev G.V., Kirillova E.A., Moskalenko U.D., Lukashev N.V., Beletskaya I.P. J. Org. Chem. 2020, 85, 9015-9028. doi: 10.1021/acs.joc.0c00931
  21. Gevondian G.A., Kotovshchikov Y.N., Latyshev G.V., Lukashev N.V., Beletskaya I.P. J. Org. Chem. 2021, 86, 5639-5650. doi: 10.1021/acs.joc.1c00115
  22. Kotovshchikov Y.N., Sultanov R.H., Latyshev G.V., Lukashev N.V., Beletskaya I.P. Org. Biomol. Chem. 2022, 20, 5764-5770. doi: 10.1039/D2OB00909A
  23. Barluenga J., Tomás-Gamasa M., Aznar F., Valdés C. Nat. Chem. 2009, 1, 494-499. doi: 10.1038/nchem.328
  24. Paraja M., Plaza M., Valdés C. Synlett. 2017, 28, 2373-2389. doi: 10.1055/s-0036-1590868
  25. Yildiz-Oren I., Tekiner-Gulbas B., Yalcin I., Temiz-Arpaci O., Akı-Sener E., Altanlar N. Arch. Pharm. Pharm. Med. Chem. 2004, 337, 402-410. doi: 10.1002/ardp.200300851
  26. Ertan T., Yildiz I., Tekiner-Gulbas B., Bolelli K., Temiz-Arpaci O., Ozkan S., Kaynak F., Yalcin I., Aki E. Eur. J. Med. Chem. 2009, 44, 501-510. doi: 10.1016/j.ejmech.2008.04.001
  27. Lage H., Aki-Sener E., Yalcin I. Int. J. Cancer. 2006, 119, 213-220. doi: 10.1002/ijc.21792
  28. Oksuzoglu E., Tekiner-Gulbas B., Alper S., Temiz-Arpaci O., Ertan T., Yildiz I., Diril N., Sener-Aki E., Yalcin I. J. Enzyme Inhib. Med. Chem. 2008, 23, 37-42. doi: 10.1080/14756360701342516
  29. Peng C., Zhang W., Yan G., Wang J. Org. Lett. 2009, 11, 1667-1670. doi: 10.1021/ol900362d
  30. Bomio C., Kabeshov M.A., Lit A.R., Lau S.-H., Ehlert J., Battilocchio C., Ley S.V. Chem. Sci. 2017, 8, 6071-6075. doi: 10.1039/C7SC02264F

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2023 Russian Academy of Sciences