Investigation of the kinetic of palladium catalysts with 2-metoxy-phenyl-dipheroccenyl- and metoxy-phenyl-dipheroccenyl-phosphin ligands in Suzuki-Miyara reaction

  • A. Khabiyev K.I. Satpayev Kazakh National Technical University, Almaty
  • Ch. Gebler Chemnitz University of Technology, Chemnitz
  • H. Lang Chemnitz University of Technology, Chemnitz
  • B. Selenova K.I. Satpayev Kazakh National Technical University, Almaty
Keywords: palladium catalysts, C, C-cross-coupling reactions, Suzuki-Miyara reaction, homogeneous catalyses

Abstract

The article represents results of the study on kinetic of palladium catalyst with 2-metoxy-phenyl-diferoccenyl- and phenyl-diferoccenyl-phosphin ligands in Suzuki-Miyara test-reactions. The advantage of Suzuki reactions in difference from other cross-coupling reactions is the use of insensitive to water and oxygen thermostable organoboron compounds. As boronic acid was used phenylboronic acid and as weak base – potassium phosphate. All used catalysts showed good activity with arylbromides and weak activity with arylchlorides.

References

1. Coleman R.S., Walczak M.C., Campbell E.L. Total synthesis of lucilactaene, a cell cycle inhibitor active in p53-inactive cells // J. Am. Chem. Soc. – 2005. – № 127. – P. 16038-16039.

2. Schulz T., Torborg C., Schaffner B., Huang J., Zapf A., Kadyrov R., Borner A., Beller M. Practical Imidazole-Based Phosphine Ligands for Selective Palladium-Catalyzed Hydroxylation of Aryl Halides // Angew. Chem. – 2009. – № 121. – P. 936 – 939.

3. Beller M., Zapf A., Maegerlein W. Efficient Synthesis of Fine Chemicals and Organic Building Blocks Applying Palladium-Catalyzed Coupling Reactions // W. Chem. Eng. Technol. – 2001. – № 24. – P. 575–582.

4. Baumeister P., Seifert G., Steiner H. Process for the preparation of substituted benzenes and benzene sulfonic acid and derivatives thereof and a process for the preparation of N'N-substituted ureas // EP 0584043 A1, 1992.

5. Nicolaou, K. C., Bulger P. G., Sarlah. D. // Angew. Chem. Int. Ed. – 2005. – № 44. – P. 4442 –4489.

6. Littke A. F., Fu G. C. Palladium-catalyzed coupling reactions of aryl chlorides // Angew. Chem. Int. Ed. – 2002. – № 41. – P. 4176 – 4211.

7. Grushin V. V., Alper H. N-Heterocyclic carbene–palladium(II)-1-methylimidazole complex catalyzed Mizoroki - Heck reaction of aryl chlorides with styrenes // Chem. Rev. – 1994. – № 94. - P. 1047 –1062.

8. Cornils B., Herrmann, W. A., Schlogl R., Wong C.-H, Zanthgoff H-W. Catalysis from A to Z. – 4th ed. – Weinheim: Wiley-VCH, 2013. – 2516 p.

9. Steinborn D. Grundlagen der metallorganischen Komplexkatalyse. – 2nd ed. – Wiesbaden: Vieweg + B.G.. Teubner Verlag, 2010. – 434 p.

10. Hagen J. Industrial Catalysis – A Practical Approach. – 2nd ed. – Weinheim: Wiley – VCH, 2006. – 493 p.

11. De Vos D. E., Vankelecom I.F.G., Jacobs P.A. Chiral catalyst immobilization and recycling. – Weinheim: Wiley – VCH, 2000. – 307 p.

12. Cornils B. Multiphase homogeneous catalysis. – Weinheim: Wiley-VCH, 2005. – 853 p.

13. Wasserscheid P., Welton T. Ionic Liquids in Synthesis. – 2nd ed. – Weinheim: Wiley-VCH, 2007. – 776 p.

Published
2014-04-28
How to Cite
Khabiyev, A., Gebler, C., Lang, H., & Selenova, B. (2014). Investigation of the kinetic of palladium catalysts with 2-metoxy-phenyl-dipheroccenyl- and metoxy-phenyl-dipheroccenyl-phosphin ligands in Suzuki-Miyara reaction. Chemical Bulletin of Kazakh National University, (1), 3-8. https://doi.org/https://doi.org/10.15328/chemb_2014_13-8
Section
Catalysis and Petrochemistry