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A copper-catalyzed reaction between terminal alkynes, acetylenic esters, and oxiranes: efficient synthesis of 2H-pyran-4-carboxylate

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Abstract

A catalytic reaction between terminal alkynes, acetylenic esters, and oxiranes has been described. This domino transformation serves as a useful sequential and one-pot method for the synthesis of 2H-pyran-4-carboxylate skeletons from the readily available starting materials. In situ-generated copper acetylides treated initially with oxiranes in the presence of copper catalysts and tetrabutylphosphonium salts, followed by addition of propiolates after 60 min to form synthetically important heterocycles.

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Acknowledgements

We wish to thank for a grant from Islamic Azad University, South Tehran Branch.

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Authors and Affiliations

  1. Department of Applied Chemistry, Faculty of Science, South Tehran Branch, Islamic Azad University, Tehran, Iran

    Milad Jahanshad, Mohammadreza Manafi & Seyed Saied Homami

  2. Department of Chemistry, Buinzahra Branch, Islamic Azad University, Buinzahra, Iran

    Seyed Mahmoud Mousavi-Safavi

  3. Department of Chemistry, Center for Catalysis Research and Innovation, BAHERENERGY Institute of Technology, P.O. Box 13487-55613, Tehran, Iran

    Majid Ghazanfarpour-Darjani

Authors
  1. Milad Jahanshad
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  2. Mohammadreza Manafi
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  3. Seyed Mahmoud Mousavi-Safavi
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  4. Seyed Saied Homami
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  5. Majid Ghazanfarpour-Darjani
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Correspondence to Mohammadreza Manafi or Majid Ghazanfarpour-Darjani.

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Jahanshad, M., Manafi, M., Mousavi-Safavi, S.M. et al. A copper-catalyzed reaction between terminal alkynes, acetylenic esters, and oxiranes: efficient synthesis of 2H-pyran-4-carboxylate. Monatsh Chem 151, 113–122 (2020). https://doi.org/10.1007/s00706-019-02526-z

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  • DOI: https://doi.org/10.1007/s00706-019-02526-z

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