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Synthesis of heteropolynuclear CuI and PdII complexes with polymeric 2,2′-biquinoline-containing ligands and investigation of their catalytic activity in the Sonogashira couplings

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Abstract

A method for electrosynthesis of heteropolynuclear biquinoline-containing CuI and PdII complexes using sacrificial Cu and Pd anodes was developed. The sequence of anode dissolution (first Pd and then Cu) was important for the synthesis of the complex. The opposite sequence of dissolution resulted in oxidation of the initially formed CuI ions to CuII. The obtained CuI and PdII complexes with polymer ligands had high catalytic activity in the reaction of aryl halides with phenylacetylene giving rise to a C(sp2)-C(sp) bond. The yield of arylphenylacetylene in the presence of 0.1 mol.% of Pd catalyst in relation to the starting halide was 50–90% depending on the nature of the aryl halide.

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References

  1. D. E. Fogg, E. N. dos Santos, Coord.Chem. Rev., 2004, 248, 2365.

    Article  CAS  Google Scholar 

  2. J.-C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev., 2005, 105, 1001.

    Article  CAS  Google Scholar 

  3. B. H. Lipshutz, D. M. Nihan, E. Vinogradova, B. R. Taft, Z. V. Boskovic, Org. Lett., 2008, 10, 4279.

    Article  CAS  Google Scholar 

  4. P. Eibracht, L. Barfacker, C. Buss, C. Holmann, B. E. Kitsos-Rzychon, L. Kranemann, T. Rische, R. Roggenbuck, A. Schmidt, Chem.Rev., 1999, 99, 3329.

    Article  Google Scholar 

  5. F. X. Felpin, E. Fouquet, Chem. Sus. Chem., 2008, 1, 718.

    CAS  Google Scholar 

  6. R. Chinchilla, C. Najera, Chem. Rev., 2007, 107, 874.

    Article  CAS  Google Scholar 

  7. J.-P. Corbet, G. Mignani, Chem. Rev., 2006, 106, 2651.

    Article  CAS  Google Scholar 

  8. J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev., 2002, 102, 1359.

    Article  CAS  Google Scholar 

  9. G. Polotskaya, M. Goikhman, I. Podeshvo, V. Kudryavtsev, Z. Pientka, L. Brozova, M. Bleha, Polymer, 2005, 46, 3730.

    Article  CAS  Google Scholar 

  10. T. V. Magdesieva, A. V. Dolganov, A. V. Yakimanskii, M. Ya. Goikhman, I. V. Podeshvo, V. V. Kudryavtsev, Elektrokhimiya, 2007, 43, 1194 [Russ. J. Electrochem. (Engl. Transl.), 2007, 43, 1133].

    Google Scholar 

  11. T. V. Magdesieva, A. V. Dolganov, A. V. Yakimansky, M. Ya. Goikhman, I. V. Podeshvo, Electrochimica Acta, 2008, 53, 3960.

    Article  CAS  Google Scholar 

  12. T. V. Magdesieva, A. V. Dolganov, A. V. Yakimansky, M. Ya. Goikhman, I. V. Podeshvo, Electrochimica Acta, 2009, 54, 1444.

    Article  CAS  Google Scholar 

  13. T. V. Magdesieva, O. M. Nikitin, R. M. Abdullin, O. V. Polyakova, A. V. Yakimanskii, M. Ya. Goikhman, I. V. Podeshvo, Izv. Akad. Nauk, Ser. Khim., 2009, 1382 [Russ. Chem. Bull. Int. Ed., 2009, 58, No. 7].

    Google Scholar 

  14. L. Brandsma, Synthesis of Acetylenes, Allenes and Cumulenes: Methods and Techniques, Elsevier, Oxford, 2004, 293 pp.

    Google Scholar 

  15. K. Sonogashira, in Metal-Catalyzed Cross-Coupling Reactions, Eds F. Diederich, A. de Meijera, Wiley-VCH, Weinheim, 2004, Vol. 1, 319 pp.

    Google Scholar 

  16. K. Sonogashira, in Handbook of Organopalladium Chemistry for Organic Synthesis, Eds E. Negishi, A. de Meijere, Wiley-Interscience, New York, 2002, 493 pp.

    Google Scholar 

  17. J. P. Corbet, Geard Mignani, Chem. Rev., 2006, 106, 2651.

    Article  CAS  Google Scholar 

  18. M. C. Chakravorti, C. V. B. Subrahmanyam, Coord. Chem. Rev., 1994, 135, 65.

    Article  Google Scholar 

  19. S. S. Kamath, V. Uma, T. S. Srivastava, Inorg. Chim. Acta, 1989, 161, 49.

    Article  CAS  Google Scholar 

  20. M. T. Reetz, W. Helbig, S. A. Quaiser, Chem. Mater., 1995, 7, 2227.

    Article  CAS  Google Scholar 

  21. T. V. Magdesieva, A. V. Dolganov, P. M. Poleshchuk, A. V. Yakimanskii, M. Ya. Goikhman, I. V. Podeshvo, V. V. Kudryavtsev, Izv. Akad. Nauk. Ser. Khim., 2007, 1331 [Russ. Chem. Bull., Int. Ed., 2007, 56, 1380].

    Google Scholar 

  22. J. Gil-Molto, C. Najera, Adv. Synth. Catal. 2006, 348, 1874.

    Article  CAS  Google Scholar 

Download references

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Correspondence to T. V. Magdesieva.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 335–340, February, 2010.

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Magdesieva, T.V., Nikitin, O.M., Yakimansky, A.V. et al. Synthesis of heteropolynuclear CuI and PdII complexes with polymeric 2,2′-biquinoline-containing ligands and investigation of their catalytic activity in the Sonogashira couplings. Russ Chem Bull 59, 342–347 (2010). https://doi.org/10.1007/s11172-010-0085-4

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  • DOI: https://doi.org/10.1007/s11172-010-0085-4

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