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

封面

如何引用文章

全文:

开放存取 开放存取
受限制的访问 ##reader.subscriptionAccessGranted##
受限制的访问 订阅存取

详细

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%.

作者简介

A. Gevondian

M.V. Lomonosov Moscow State University

Y. Kotovshchikov

M.V. Lomonosov Moscow State University

Email: kotovshchikov@org.chem.msu.ru

G. Latyshev

M.V. Lomonosov Moscow State University

N. Lukashev

M.V. Lomonosov Moscow State University

I. Beletskaya

M.V. Lomonosov Moscow State University

参考

  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

补充文件

附件文件
动作
1. JATS XML
下载

版权所有 © Russian Academy of Sciences, 2023