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One-pot catalyst-free stereoselective N-acylvinylation/C-phosphorylation of phenanthridine in the aryl(hetaryl)acetylenic ketone—secondary phosphine oxide system

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Abstract

Phenanthridine readily undergoes one-pot N-acylvinylation/C-phosphorylation in the terminal acetylenic ketone—secondary phosphine oxide system at room temperature (acetonitrile, 48–72 h) in the absence of a catalyst to stereoselectively form (E)-N-acylvinyl-6-diorganylphosphoryl-5,6-dihydrophenanthridines in up to 88% preparative yield. Under similar conditions, secondary phosphine sulfides form a difficult-to-separate mixture of N-vinylation/C-phosphorylation products and adducts of phosphine sulfides with acetylenic ketones, while bis(2-phenylethyl)phosphine selenide gives only an adduct with acetylenic ketone in 78% yield.

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Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation

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

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

Correspondence to B. A. Trofimov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

Structural studies of the synthesized compounds were carried out using the equipment of the Baikal Analytical Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences.

This work was financially supported by the Russian Science Foundation (Project No. 18-73-1008011).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 4, pp. 955–959, April, 2023.

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Volkov, P.A., Khrapova, K.O., Telezhkin, A.A. et al. One-pot catalyst-free stereoselective N-acylvinylation/C-phosphorylation of phenanthridine in the aryl(hetaryl)acetylenic ketone—secondary phosphine oxide system. Russ Chem Bull 72, 955–959 (2023). https://doi.org/10.1007/s11172-023-3859-5

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  • DOI: https://doi.org/10.1007/s11172-023-3859-5

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