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Polyaromatic Products of Three-Component Coupling of Aryl Halide with Two Molecules of Arylacetylene and Arylboronic Acid under Ligand-Free Catalysis Conditions

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Abstract

The aryl halide-arylacetylene-arylboronic acid three-component coupling in the presence of a Pd catalyst containing no organic ligands is described. The reaction routes that take place in the reaction system are shown to include the consecutive carbopalladation of two arylacetylene molecules, leading to unsaturated polyaromatic compounds. The possibility of controlling the alternative reaction routes is demonstrated.

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References

  1. Gildner, P.G. and Colacot, T.J., Organometallics, 2015, vol. 34, p. 5497. doi https://doi.org/10.1021/acs.organomet.5b00567

    Article  CAS  Google Scholar 

  2. Zhou, C., Emrich, D.E. and Larock, R.C., Org. Lett., 2003, vol. 5, p. 1579. doi 10.1021/ol034435d

    Article  CAS  PubMed  Google Scholar 

  3. Zhou, C. and Larock, R.C., J. Org. Chem., 2005, vol. 70, p. 3765. doi 10.1021/jo048265+

    Article  CAS  PubMed  Google Scholar 

  4. Larina, E.V., Kurokhtina, A.A., Yarosh, E.V., Lagoda, N.A., and Schmidt, A.F., Russ. J. Org. Chem., 2016, vol. 52, p. 1356. doi https://doi.org/10.1134/S1070428016090190

    Article  CAS  Google Scholar 

  5. Horiguchi. H., Tsurugi, H., Satoh, T., and Miura, M., Adv. Synth. Catal., 2008, vol. 350, p. 509. doi https://doi.org/10.1002/adsc.200700533

    Article  CAS  Google Scholar 

  6. Wen, Y., Huang, L., and Jiang, H., J. Org. Chem., 2012, vol. 77, p. 5418. doi https://doi.org/10.1021/jo300662x

    Article  CAS  PubMed  Google Scholar 

  7. Shibata, K., Satoh, T., and Miura, M., Org. Lett., 2005, vol. 7, p. 1781. doi 10.1021/ol0503743

    Article  CAS  PubMed  Google Scholar 

  8. Pal, M., Parasuraman, K., Subramanian, V., Dakarapu, R., and Yeleswarapu, K.R., Tetrahedron Lett., 2004, vol. 45, p. 2305. doi https://doi.org/10.1016/j.tetlet.2004.01.113

    Article  CAS  Google Scholar 

  9. Shi, M., Liu, L.-P., and Tang, J., Org. Lett., 2005, vol. 7, p. 3085. doi 10.1021/ol051101a

    Article  CAS  PubMed  Google Scholar 

  10. Campeau, L.-C., Parisien, M., Jean, A., and Fagnou, K., J. Am. Chem. Soc., 2006, vol. 128, p. 581. doi https://doi.org/10.1021/ja055819x

    Article  CAS  PubMed  Google Scholar 

  11. Turker, L., Tapan, A., and Gumus, S., Polycycl. Aromat. Compd., 2009, vol. 29, p. 123. doi https://doi.org/10.1080/10406630902956260

    Article  CAS  Google Scholar 

  12. Wu, G., Rheingold, A.L., Geib, S.J., and Heck, R.F., Organometallics, 1987, vol. 6, p. 1941. doi 10.1021/om00152a019

    Article  CAS  Google Scholar 

  13. Horiguchi, H., Hirano, K., Satoh, T., and Miura, M., Adv. Synth. Catal., 2009, vol. 351, p. 1431. doi 10.1002/adsc.200900096

    Article  CAS  Google Scholar 

  14. Wu, Y.-T., Huang, K.-H., Shin, C.-C., and Wu, T.-C., Chem. Eur. J., 2008, vol. 14, p. 6697. doi 10.1002/chem.200800538

    Article  CAS  PubMed  Google Scholar 

  15. Bej, A., Chakraborty, A., and Sarkar, A., RSC Adv., 2013, vol. 3, p. 15812. doi 10.1039/C3RA41924J

    Article  CAS  Google Scholar 

  16. Satoh, T., Ogino, S., Miura, M., and Nomura, M., Angew. Chem. Int. Ed., 2004, vol. 43, p. 5063. doi 10.1002/anie.200460409

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Irkutsk State University, ul. K. Marksa 1, Irkutsk, 664003, Russia

    E. V. Yarosh, E. V. Larina, N. A. Lagoda, A. A. Kurokhtina & A. F. Schmidt

Authors
  1. E. V. Yarosh
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  2. E. V. Larina
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  3. N. A. Lagoda
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  4. A. A. Kurokhtina
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  5. A. F. Schmidt
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Corresponding author

Correspondence to A. F. Schmidt.

Additional information

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 5, pp. 782–786.

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Yarosh, E.V., Larina, E.V., Lagoda, N.A. et al. Polyaromatic Products of Three-Component Coupling of Aryl Halide with Two Molecules of Arylacetylene and Arylboronic Acid under Ligand-Free Catalysis Conditions. Russ J Org Chem 55, 678–681 (2019). https://doi.org/10.1134/S1070428019050154

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  • DOI: https://doi.org/10.1134/S1070428019050154

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