Synthesis of bicyclo[2.2.1]heptane derivatives via one-pot three-component coupling of norbornene with aryl halide and arylacetylene using “ligand-free” pd catalytic systems

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Resumo

The results of Pd-catalyzed difunctionalization of norbornene via one-pot three-component coupling of norbornene, aryl halide and arylacetylene with new C(sp3)−C(sp2)/C(sp3) −C(sp) bond formation are presented. The convenience of the proposed approach compared to other methods is the use of a simple and accessible “ligand-free” catalytic system based on palladium salts and an inorganic base to obtain valuable bicyclo[2.2.1]heptane derivatives.

Sobre autores

E. Larina

Irkutsk State University, Chemical Department

ul. K. Marksa 1, Irkutsk, 664003 Russia

N. Lagoda

Irkutsk State University, Chemical Department

ul. K. Marksa 1, Irkutsk, 664003 Russia

A. Kurokhtina

Irkutsk State University, Chemical Department

ul. K. Marksa 1, Irkutsk, 664003 Russia

A. Schmidt

Irkutsk State University, Chemical Department

Email: aschmidt@chem.isu.ru
ul. K. Marksa 1, Irkutsk, 664003 Russia

Bibliografia

  1. Fu X., Zhao W. Chin. J. Org. Chem. 2019, 39 (3), 625–647. doi: 10.6023/cjoc201808031
  2. Li Y., Wu D., Cheng H.-G., Yin G. Angew. Chem., Int. Ed. 2020, 59, 7990–8003. doi: 10.1002/anie.201913382
  3. Ma R., Fang S., Jiang H., Wu W. Org. Lett. 2024, 26, 2354–2358. doi: 10.1021/acs.orglett.4c00051
  4. Pounder A., Ho A., Macleod M., Tam W. Curr. Org. Synth. 2021, 18, 446–474. doi: 10.2174/1570179417666210105121115
  5. Khan R., Chen J., Fan B. Adv. Synth. Catal. 2020, 362, 1564–1601. doi: 10.1002/adsc.201901494
  6. Dragutan V., Demonceau A., Organometallic Polymers by Ring-Opening Metathesis Polymerization (ROMP) Reactions, Reference Module in Chemistry, Molecular Sciences and Chemical Engineering Elsevier, 2018, 1–11. doi: 10.1016/B978-0-12-409547-2.14232-5.
  7. Li M., Cai Z., Eisen M.S. Inorg. Chem. 2024, 63 (4), 1774–1783. doi: 10.1021/acs.inorgchem.3c03093
  8. Della Ca' N., Fontana M., Motti E., Catellani М. Acc. Chem. Res. 2016, 49 (7), 1389–1400. doi: 10.1021/acs.accounts.6b00165
  9. Li R., Dong G. J. Am. Chem. Soc. 2020, 142 (42), 17859–17875. doi: 10.1021/jacs.0c09193
  10. Chen C., Song J.-H., Ding L.-Y., Zhang X.-X., Wang K., Ni C., Hu J., Zhu B. Org. Lett. 2024, 26 (27), 5770–5775. doi: 10.1021/acs.orglett.4c01944
  11. Pounder A., Neufeld E., Myler P., Tam W. Beilstein J. Org. Chem. 2023, 19, 487–540. doi: 10.3762/bjoc.19.38
  12. Shi Y., Ji C.-L., Liu C. J. Org. Chem. 2023, 88, 261–271. doi: 10.1021/acs.joc.2c02295
  13. Li Z., Zheng J., Li C., Wu W., Jiang H. Chin. J. Chem. 2019, 37 (2), 140–147. doi: 10.1002/cjoc.201800536
  14. Xu T., Zhou X., Han Y., Zhang L., Liu L., Huang T., Li C., Tang Z., Wan S., Chen T. Tetrahedron Lett. 2022, 97, 153799. doi: 10.1016/j.tetlet.2022.153799
  15. Niu T., Zhao X., Jiang J., Yan H., Li Y., Tang S., Li Y., Song D. Molecules 2019, 24, 921. doi: 10.3390/molecules24050921
  16. Che J.-X., Wang Z.-L., Dong X.-W., Hu Y.-H., Xie X., Hu Y.-Z. RSC Adv. 2018, 8, 11061–11069. doi: 10.1039/C8RA01806E
  17. Frank D., Espeel P., Badi N., Prez F.D. Eur. Polym. J. 2018, 98, 246–253. doi: 10.1016/j.eurpolymj.2017.11.023
  18. Zhuang R., Liu H., Guo J., Dong B., Zhao W., Hu Y., Zhang X. Eur. Polym. J. 2017, 93, 358–367. doi: 10.1016/j.eurpolymj.2017.06.018
  19. Radzinski S.C., Foster J.C., Chapleski R.C. Jr., Troya D., Matson J.B. J. Am. Chem. Soc. 2016, 138, 6998–7004. doi: 10.1021/jacs.5b13317
  20. Choi C., Hong J., Tomita I., Endo T.B. Korean. Chem. Soc. 2002, 23, 112–118. doi: 10.5012/bkcs.2002.23.1.112
  21. Catellani M., Chiusoli P.G. Tetrahedron Lett. 1982, 23, 4517–4520. doi: 10.1016/S0040-4039(00)85642-7
  22. Motti E., Rossetti M., Bocelli G., Catellani M. J. Organomet. Chem. 2004, 689 (23), 3741–3749. doi: 10.1016/j.jorganchem.2004.05.035
  23. Catellani M., Chiusoli G.P., Concari S. Tetrahedron 1989, 45, 5263–5268. doi: 10.1016/S0040-4020(01)81100-5
  24. Kuo C.-J., Cheng S.-J., Chang S.-T., Liu C.-H. Eur. J. Org. Chem. 2008, 3, 485–491. doi: 10.1002/ejoc.200700772
  25. Gömöry Á., Somogyi Á., Tamás J., Stájer G., Ber- náth G., Komáromi I. Int. J. Mass Spectrom. Ion Processes 1991, 107, 225–246. doi: 10.1016/0168-1176(91)80061-Q
  26. Larina E.V., Kurokhtina A.A., Vidyaeva E.V., Lago- da N.A., Schmidt A.F. Mol. Catal. 2021, 513, 111778. doi: 10.1016/j.mcat.2021.111778
  27. Ярош Е.В., Ларина Е.В., Лагода Н.А., Курохти- на А.А., Шмидт А.Ф. ЖОрХ. 2019, 55 (5), 781–785. [Yarosh E.V., Larina E.V., Lagoda N.A., Kurokhti- na A.A., Schmidt A.F. Russ. J. Org. Chem. 2019, 55 (5), 678–681.] doi: 10.1134/S1070428019050154
  28. Schmidt A.F., Kurokhtina A.A., Larina E.V., Vidyae- va E.V., Schmidt E.Y., Lagoda N.A. ChemCatChem 2020, 12 (21), 5523–5533. doi: 10.1002/cctc.202000925
  29. Лагода Н.А., Видяева Е.В., Ларина Е.В., Курохти- на А.А., Шмидт А.Ф. ЖОрХ. 2021, 57 (1), 92–102. [Lagoda N.A., Vidyaeva E.V., Larina E.V., Kurokhti- na A.A., Schmidt A.F. Russ. J. Org. Chem. 2021, 57 (1), 71–78.] doi: 10.1134/S1070428021010103
  30. Шмидт А.Ф., Аль-Халайка А., Смирнов В.В., Курох-тина А.А. Кинетика и катализ. 2008, 49, 669 –674. [Schmidt A.F., Al-Halaiqa A., Smirnov V.V., Kurokhtina A.A. Kinet. Catal. 2008, 49, 638–643.]
  31. Шмидт А.Ф., Маметова Л.В., Дмитриева Е.В., Шмидт Е.Ю., Ткач В.С. Изв. АН СССР. Сер. хим. 1991, 40 (1), 208.
  32. Курохтина А.А., Ларина Е.В., Ярош Е.В., Шмидт А.Ф. Кинетика и катализ. 2016, 57 (3), 376–382. [Kurokhtina A.A., Larina E.V., Yarosh E.V., Schmidt A.F. Kinet. Catal. 2016, 57 (3), 373–379.] doi: 10.1134/S0023158416030095
  33. Fernández E., Rivero-Crespo M.A., Domínguez I., Rubio-Marqués P., Oliver-Meseguer J., Liu L., Cabrero-Antonino M., Gavara R., Hernández-Garrido J.C., Boronat M., Leyva-Pérez A., Corma A. J. Am. Chem. Soc. 2019, 141 (5), 1928–1940. doi: 10.1021/jacs.8b07884
  34. Fantoni T, Bernardoni S, Mattellone A, Martelli G., Ferrazzano L., Cantelmi P., Corbisiero D., Tolomelli A., Cabri W., Vacondio F., Ferlenghi F., Mor M., Ricci A. ChemSusChem. 2021, 14 (12), 2591–2600. doi: 10.1002/cssc.202100623
  35. Zhao Z., Wang J., Zhang X., Lin T., Ren J., Pang W. Tetrahedron Lett. 2022, 100, 153849. doi: 10.1016/j.tetlet.2022.153849.

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