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Chemoselective Synthesis of Alkylphosphinic Acids from Red Phosphorus and Alkyl Bromides in the System KOH/H2O/Toluene/Micellar Catalyst

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Abstract

Alkylphosphinic acids, including long-chain ones, were synthesized in up to 76% yields from red phosphorus and n-AlkBr (Alk = C4–C14) under micellar catalysis conditions. The reaction proceeds efficiently and chemoselectively upon heating (85–90°C, 6 h) in a KOH/H2O/toluene/cetyltrimethylammonium bromide system.

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ACKNOWLEDGMENTS

The structure of the synthesized compounds was studied using the equipment of the Baikal Analytical Center for Collective Use, Siberian Branch, Russian Academy of Sciences.

Funding

The work was financially supported by the Council for Grants of the President of the Russian Federation for State Support of Russian Young PhD Scientists (grant no. MK-5606.2021.1.3).

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Authors and Affiliations

  1. Favorskii Irkutsk institute of Chemistry, Siberian Branch, Russian Academy of Sciences (SB RAS), 664033, Irkutsk, Russia

    S. F. Malysheva, V. A. Kuimov, N. A. Belogorlova, K. O. Khrapova & N. K. Gusarova

  2. Scientific Center SB RAS, 664033, Irkutsk, Russia

    K. A. Apartsin

Authors
  1. S. F. Malysheva
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  2. V. A. Kuimov
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  3. N. A. Belogorlova
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  4. K. O. Khrapova
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  5. K. A. Apartsin
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  6. N. K. Gusarova
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Correspondence to N. K. Gusarova.

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Malysheva, S.F., Kuimov, V.A., Belogorlova, N.A. et al. Chemoselective Synthesis of Alkylphosphinic Acids from Red Phosphorus and Alkyl Bromides in the System KOH/H2O/Toluene/Micellar Catalyst. Russ J Org Chem 58, 192–199 (2022). https://doi.org/10.1134/S1070428022020063

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