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Microwave-assisted Sonogashira cross-coupling reaction catalyzed by CN-ortho-palladated complex of tribenzylamine under copper-free conditions

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Abstract

The catalytic activity of [Pd{C6H4(CH2N(CH2Ph)2)} (µ-Br)]2 complex as an efficient, stable and non-sensitive to air and moisture catalyst was investigated in the Sonogashira cross-coupling reaction under microwave irradiation. In the presence of catalytic amount of this homogeneous catalytic system, various aryl halides were efficiently coupled with phenylacetylene under copper-free conditions. The substituted internal alkynes were produced in excellent yields in short reaction times in NMP at 100 °C. The combination of dimeric complex as homogenous catalyst and microwave irradiation and also NMP as microwave-active polar solvent gave higher yields in shorter reaction times.

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Acknowledgments

We gratefully acknowledge the funding support received for this project from the Isfahan University of Technology (IUT), IR Iran and Isfahan Science & Technology Town (ISTT), IR, Iran. We also gratefully acknowledge the partial financial support received from the research council of Alzahra University.

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Authors and Affiliations

  1. Pharmaceutical Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan, 84156, Islamic Republic of Iran

    Abdol R. Hajipour

  2. Department of Chemistry, Faculty of Science, Alzahra University, Vanak, Tehran, Iran

    Fatemeh Rafiee

Authors
  1. Abdol R. Hajipour
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  2. Fatemeh Rafiee
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Correspondence to Abdol R. Hajipour.

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Hajipour, A.R., Rafiee, F. Microwave-assisted Sonogashira cross-coupling reaction catalyzed by CN-ortho-palladated complex of tribenzylamine under copper-free conditions. J IRAN CHEM SOC 12, 1163–1169 (2015). https://doi.org/10.1007/s13738-014-0577-5

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