Palladium complex compounds as catalysts for cross-coupling reactions for obtaining functional materials

Part 1. Sonogashira reaction
Platonova Ya.B., Leonov A.A., Kirillova V.A., Savilov S. V.
UDC
544.47:661.898
DOI
10.18577/2307-6046-2026-0-6-118-128
Article PDF (Russian) (1.24 MB)
How to cite
Platonova Ya.B., Leonov A.A., Kirillova V.A., Savilov S. V. Palladium complex compounds as catalysts for cross-coupling reactions for obtaining functional materials. Part 1. Sonogashira reaction // Proceedings of VIAM. 2026. No. 6. DOI: 10.18577/2307-6046-2026-0-6-118-128. URL: https://test.viam.ru/en/journal/2026/6/11
Keywords
Sonogashira reaction, biologically active compounds, pincer complexes, N-heterocyclic carbene complexes of palladium, phthalocyanines, controlled palladium release
Abstract

The review systematizes approaches to the development of homogeneous and heterogeneous catalytic systems on the basis of a multitude of palladium complexes for the Sonogashira reaction. Strategies for the controlled release of active metal particles that prevent the formation of inactive palladium black are thoroughly covered. The advantages of immobilization on magnetic supports are shown, allowing reactions to be carried out under mild conditions with the possibility of repeated use of the catalyst. The potential of phthalocyanine complexes, which allow obtaining biologically active compounds with high products yields, is noted.

Reference list
  1. Wang D., Gao S. Sonogashira coupling in natural product synthesis. Organic Chemistry Frontiers, 2014, vol. 1, no. 5, pp. 556–566. DOI: 10.1039/C3QO00086A.
  2. Yan F., Zhang X., Li D. et al. Recent applications of the Sonogashira reaction in the synthesis of drugs and their derivatives: A review. Applied Organometallic Chemistry, 2025, vol. 39, no. 1, p. e7932. DOI: 10.1002/aoc.7932.
  3. Röhlich C., Köhler K. Macrocyclic Palladium(II) Complexes in C–C Coupling Reactions: Efficient Catalysis by Controlled Temporary Release of Active Species. Advanced Synthesis & Catalysis, 2010, vol. 352, no. 13, pp. 2263–2274. DOI: 10.1002/adsc.201000458.
  4. Sonogashira K., Tohda Y., Hagihara N. A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines. Tetrahedron letters, 1975, vol. 16, no. 50, pp. 4467–4470. DOI: 10.1016/S0040-4039(00)91094-3.
  5. Johar M., Manning T., Tse C. et al. Growth Inhibition of Mycobacterium bovis, Mycobacterium tuberculosis and Mycobacterium avium In Vitro: Effect of 1-α-D-2′-Arabinofuranosyl and 1-(2′-Deoxy-2′-fluoro-α-D-2′-ribofuranosyl) Pyrimidine Nucleoside Analogs. Journal of Medicinal Chemistry, 2007, vol. 50, pp. 3696–3705. DOI: 10.1021/jm0703901.
  6. Shakya N., Srivastav N.C., Desroches N. et al. 3′-Bromo Analogues of Pyrimidine Nucleosides as a New Class of Potent Inhibitors of Mycobacterium tuberculosis. Journal of Medicinal Chemistry, 2010, vol. 53, pp. 4130–4140. DOI: 10.1021/jm100165w.
  7. Dolgova E.V. Application of cyanate ester materials. Part 2. Microelectronics, 3D printing, radiation protection. Trudy VIAM, 2023, no. 1 (119), pр. 139–156. Available at: http://www.viam-works.ru (accessed: April 06, 2026). DOI: 10.18577/2307-6046-2023-0-1-139-156.
  8. Seri M., Marrocchi A. The carbon–carbon triple bond as a tool to design organic semiconductors for photovoltaic applications: an assessment of prospects and challenges. Journal of Materials Chemistry C, 2021, vol. 9, no. 45, pp. 16164–16186. DOI: 10.1039/D1TC02958D.
  9. Lyubimova A.S., Tkachuk A.I., Kuznetsova P.A. Shape memory epoxy polymers. Trudy VIAM, 2024, no. 4 (134), pp. 50–63. Available at: http://www.viam-works.ru (accessed: April 06, 2026). DOI: 10.18577/2307-6046-2024-0-4-50-63.
  10. Bespalov A.S., Salimov I.E., Yudin A.V. Imparting highly hydrophobic properties to a high-porous ceramic material with low-concentration solutions of fluoroparaffin in a supercritical carbon dioxide environment. Aviation materials and technologies, 2025, no. 1 (78), pp. 39‒48. Available at: http://www.journal.viam.ru (accessed: April 06, 2026). DOI: 10.18577/2713-0193-2025-0-1-39-48.
  11. Silvestri F., Marrocchi A. Acetylene-based materials in organic photovoltaics. International journal of molecular sciences, 2010, vol. 11, no. 4, pp. 1471–1508. DOI: 10.3390/ijms11041471.
  12. Marchenko S.A., Zheleznyak V.G., Kuznetsova V.A. Application and modification of particles to create superhydrophobic coatings (review). Trudy VIAM, 2023, no. 5 (123), pp. 94–110. Available at: http://www.viam-works.ru (accessed: April 06, 2026). DOI: 10.18577/2307-6046-2023-0-5-94-110.
  13. Marchenko S.A., Zheleznyak V.G., Kuznetsova V.A., Timoshina E.A. Dependence of ice adhesion on the hydrophobic properties of polymer coatings, applied of pneumatic spraying method. Trudy VIAM, 2024, no. 2 (132), pp. 76–83. Available at: http://www.viam-works.ru (accessed: April 06, 2026). DOI: 10.18577/2307-6046-2024-0-2-76-83.
  14. He B., Huang J., Liu X. et al. Polymerizations of activated alkynes. Progress in Polymer Science, 2022, vol. 126, p. 101503. DOI: 10.1016/j.progpolymsci.2022.101503.
  15. Bhaskar R., Sharma A.K., Yadav M.K., Singh A.K. Sonogashira (Cu and amine free) and Suzuki coupling in air catalyzed via nanoparticles formed in situ from Pd(II) complexes of chalcogenated Schiff bases of 1-naphthaldehyde and their reduced forms. Dalton Transactions, 2017, vol. 46, pp. 15235–15248. DOI: 10.1039/c7dt02701j.
  16. Kumar S., Saleem F., Mishra M.K., Singh A.K. Oxine based unsymmetrical (O, N, S/Se) pincer ligands and their palladium(II) complexes: synthesis, structural aspects and applications as a catalyst in amine and copper-free Sonogashira coupling. New Journal of Chemistry, 2017, vol. 41, pp. 2745–2755. DOI: 10.1039/c7nj00067g.
  17. Sabounchei S.J., Ahmadi M., Nasri Z. et al. Palladium(II) phosphine–ylide complexes as highly efficient pre-catalysts in additive- and amine-free Sonogashira coupling reactions performed under aerobic and low Pd loading conditions. Tetrahedron Letters, 2013, vol. 54, pp. 4656–4660. DOI: 10.1016/j.tetlet.2013.06.064.
  18. Karami K., Najvani S.D., Naeini N.H., Herves P. Palladium particles from oxime-derived palladacycle supported on Fe3O4/oleic acid as a catalyst for the copper-free Sonogashira cross-coupling reaction. Chinese Journal of Catalysis, 2015, vol. 36, pp. 1047–1053. DOI: 10.1016/S1872-2067(15)60837-3.
  19. Bahadorikhalili S., Ma’mani L., Mahdavi H., Shafiee A. Palladium catalyst supported on PEG-ylated imidazolium based phosphinite ionic liquid-modified magnetic silica core–shell nanoparticles: a worthy and highly water-dispersible catalyst for organic reactions in water. RSC Advanced, 2015, vol. 5, pp. 71297–71305. DOI: 10.1039/C5RA12747E.
  20. Mohammadi E., Movassagh B. A polystyrene supported [PdCl–(SeCSe)] complex: a novel, reusable and robust heterogeneous catalyst for the Sonogashira synthesis of 1,2-disubstituted alkynes and 1,3-enynes. New Journal of Chemistry, 2018, vol. 42, рр. 11471–11479. DOI: 10.1039/c8nj01042k.
  21. Zhang J.-H., Li P., Hu W.-P., Wang H.-X. Substituent effect of diiminopalladium(II) pincer complexes on the catalysis of Sonogashira coupling reaction. Polyhedron, 2015, vol. 96, pp. 107–112. DOI: 10.1016/j.poly.2015.04.031.
  22. Liu Q.-X., Cai K.-Q., Zhao Z.-X. Synthesis, structure and catalysis of a NHC–Pd(II) complex based on a tetradentate mixed ligand. RSC Advanced, 2015, vol. 5, pp. 85568–85578. DOI: 10.1039/C5RA11089K.
  23. Khajehzadeh M., Moghadam M. A new poly(N-heterocyclic carbene Pd complex) immobilized on nano silica: An efficient and reusable catalyst for Suzuki–Miyaura, Sonogashira and Heck–Mizoroki C‒C coupling reactions. Journal of Organometallic Chemistry, 2018, vol. 863, pp. 60–69. DOI: 10.1016/j.jorganchem.2018.03.030.
  24. Platonova Y.B., Volov A.N., Tomilova L.G. Palladium(II) octaalkoxy- and octaphenoxyphthalocyanines: Synthesis and evaluation as catalysts in the Sonogashira reaction. Journal of Catalysis, 2019, vol. 373, pp. 222–227. DOI: 10.1016/j.jcat.2019.04.003.
  25. Platonova Y.B., Volov A.N., Tomilova L.G. Palladium(II) phthalocyanines efficiently promote phosphine-free Sonogashira cross-coupling reaction at room temperature. Journal of Catalysis, 2020, vol. 391, pp. 224–228. DOI: 10.1016/j.jcat.2020.08.019.
  26. Volov A.N., Volov N.A., Platonova Y.B. Design and synthesis of novel 5-alkynyl pyrimidine nucleosides derivatives: Influence of C-6-substituent on antituberculosis activity. Bioorganic & Medicinal Chemistry Letters, 2021, vol. 48, p. 128261. DOI: 10.1016/j.bmcl.2021.128261.