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Chemoselective Vinylation of the Quinine Hydroxy Group with the System Electron-Deficient Acetylene/Diphenylphosphine Oxide: an Alternative to SHNAr Reaction

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Abstract

Three-component SHNAr reaction of quinine, diphenylphosphine oxide, and furoylacetylene chemoselectively afforded the corresponding quinine vinyl ether and 2: 1 adduct of diphenylphosphine oxide to the triple bond of furoylacetylene instead of the expected cross-coupling product at the pyridine ring.

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References

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Acknowledgments

The spectral and analytical data were obtained using the facilities of the Baikal Joint Analytical Center, Siberian Branch, Russian Academy of Sciences.

Funding

This study was performed under financial support by the Russian Science Foundation (project no. 18-73-10080).

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, 664033, Russia

    P. A. Volkov, A. A. Telezhkin, N. I. Ivanova, K. O. Khrapova, A. I. Albanov, N. K. Gusarova & B. A. Trofimov

Authors
  1. P. A. Volkov
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  2. A. A. Telezhkin
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  3. N. I. Ivanova
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  4. K. O. Khrapova
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  5. A. I. Albanov
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  6. N. K. Gusarova
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  7. B. A. Trofimov
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Corresponding author

Correspondence to B. A. Trofimov.

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Conflict of Interests

The authors declare the absence of conflict of interests.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 12, pp. 1938–1941.

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Volkov, P.A., Telezhkin, A.A., Ivanova, N.I. et al. Chemoselective Vinylation of the Quinine Hydroxy Group with the System Electron-Deficient Acetylene/Diphenylphosphine Oxide: an Alternative to SHNAr Reaction. Russ J Org Chem 55, 1971–1974 (2019). https://doi.org/10.1134/S1070428019120285

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  • DOI: https://doi.org/10.1134/S1070428019120285

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