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Mendeleev Communications, 2019, Volume 29, Issue 3, Pages 328–330
DOI: https://doi.org/10.1016/j.mencom.2019.05.030
(Mi mendc1513)
 

This article is cited in 11 scientific papers (total in 11 papers)

Communications

Single-stage synthesis of alkyl-H-phosphinic acids from elemental phosphorus and alkyl bromides

N. K. Gusarova, A. O. Sutyrina, V. A. Kuimov, S. F. Malysheva, N. A. Belogorlova, P. A. Volkov, B. A. Trofimov

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russian Federation
Abstract: Elemental phosphorus (red or white) reacts with alkyl bromides at 60–62°C in the phase-transfer catalytic system KOH/H2O/PhMe/Et3BnNCl to afford alkyl-H-phosphinic acids in up to 47% yield.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (272.4 Kb)


Citation: N. K. Gusarova, A. O. Sutyrina, V. A. Kuimov, S. F. Malysheva, N. A. Belogorlova, P. A. Volkov, B. A. Trofimov, “Single-stage synthesis of alkyl-H-phosphinic acids from elemental phosphorus and alkyl bromides”, Mendeleev Commun., 29:3 (2019), 328–330
Linking options:
  • https://www.mathnet.ru/eng/mendc1513
  • https://www.mathnet.ru/eng/mendc/v29/i3/p328
  • This publication is cited in the following 11 articles:
    1. Kseniya O. Khrapova, Pavel A. Volkov, Anton A. Telezhkin, Alexander I. Albanov, Oleg N. Chupakhin, Boris A. Trofimov, “Catalyst- and solvent-free regiospecific SNHAr phosphinylation of pyridines with H-phosphinates mediated by benzoylphenylacetylene”, Org. Biomol. Chem., 22:26 (2024), 5419  crossref
    2. Vladimir A. Kuimov, Svetlana F. Malysheva, Natalia A. Belogorlova, Ruslan I. Fattakhov, Alexander I. Albanov, Boris A. Trofimov, “Triton-X-100 as an Organic Catalyst for One-Pot Synthesis of Arylmethyl-H-phosphinic Acids from Red Phosphorus and Arylmethyl Halides in the KOH/H2O/Toluene Multiphase Superbase System”, Catalysts, 13:4 (2023), 720  crossref
    3. Gaukhar K. Bishimbayeva, Nina K. Gusarova, Arailym M. Nalibayeva, Svetlana I. Verkhoturova, Amangul Bold, Natalya A. Chernysheva, Assem K. Zhangabayeva, Svetlana N. Arbuzova, Yerlan N. Abdikalykov, Dinara S. Zhumabayeva, “Synthesis and Properties of Sulfur-Containing Organophosphorus Extractants Based on Red Phosphorus, Alkyl Bromides, and Elemental Sulfur”, Materials, 16:9 (2023), 3394  crossref
    4. S. F. Malysheva, V. A. Kuimov, S. N. Arbuzova, “Elemental Phosphorus in the Synthesis of Organophosphorus Compounds: The Recent Advances (A Review)”, Russ J Gen Chem, 93:S1 (2023), S238  crossref
    5. S. F. Malysheva, V. A. Kuimov, N. A. Belogorlova, K. O. Khrapova, K. A. Apartsin, N. K. Gusarova, “Chemoselective Synthesis of Alkylphosphinic Acids from Red Phosphorus and Alkyl Bromides in the System KOH/H2O/Toluene/Micellar Catalyst”, Russ J Org Chem, 58:2 (2022), 192  crossref
    6. P. A. Volkov, K. O. Khrapova, A. A. Telezhkin, S. F. Malysheva, L. I. Larina, B. A. Trofimov, “Synthesis of alkyl-H-phosphinic acid alkyl esters from red phosphorus and alkyl bromides”, Mendeleev Commun., 32:6 (2022), 792–794  mathnet  crossref
    7. Vladimir A. Kuimov, Svetlana F. Malysheva, Natalia A. Belogorlova, Alexander I. Albanov, Nina K. Gusarova, Boris A. Trofimov, “Synthesis of Long‐Chain n‐Alkylphosphonic Acids by Phosphonylation of Alkyl Bromides with Red Phosphorus and Superbase under Micellar/Phase Transfer Catalysis”, Eur J Org Chem, 2021:10 (2021), 1596  crossref
    8. Vladimir A. Kuimov, Svetlana F. Malysheva, Natalia A. Belogorlova, Nina K. Gusarova, Boris A. Trofimov, “Chemoselective synthesis of long-chain alkyl-H-phosphinic acids via one-pot alkylation/oxidation of red phosphorus with alkyl-PEGs as recyclable micellar catalysts”, Org. Biomol. Chem., 19:48 (2021), 10587  crossref
    9. N. K. Gusarova, B. A. Trofimov, “Organophosphorus chemistry based on elemental phosphorus: advances and horizons”, Russian Chem. Reviews, 89:2 (2020), 225–249  mathnet  mathnet  crossref  isi  scopus
    10. Svetlana F. Malysheva, Vladimir A. Kuimov, Natalia A. Belogorlova, Alexander I. Albanov, Nina K. Gusarova, Boris A. Trofimov, “Superbase‐Assisted Selective Synthesis of Triarylphosphines from Aryl Halides and Red Phosphorus: Three Consecutive Different SNAr Reactions in One Pot”, Eur J Org Chem, 2019:36 (2019), 6240  crossref
    11. Deepitha John, Chinaraga Pitchaiah Kancharlapalli, Sivaraman Nagarajan, “Solubility of Phenylphosphinic Acid in Supercritical Carbon Dioxide and the Influence of Methanol on the Solubility Behavior”, J. Chem. Eng. Data, 64:12 (2019), 5775  crossref
    Citing articles in Google Scholar: Russian citations, English citations
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