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Regioselective heterocyclization of mixed phosphonium-iodonium ylides with acetylenes involving dimethyl acetylenedicarboxylate

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Abstract

A new approach to the synthesis of λ5-phosphinolines was developed consisting in the reaction of mixed phosphonium-iodonium ylides with acetylenes in the presence of dimethyl acetylenedicarboxylate as a dipolarophile. The heterocyclization process under these conditions was found to be regioselective and chemoselective, giving only one of the possible isomers for both internal and terminal acetylenes. The structure of phosphinoline based on internal alkyne, 1-phenylpropyne, was confirmed by single crystal X-ray diffraction analysis. The EPR showed the presence of radical intermediates in the reaction.

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Authors and Affiliations

  1. Department of Chemistry, Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119334, Moscow, Russian Federation

    I. D. Potapov, A. Yu. Voznarskiy, A. V. Mironov & T. A. Podrugina

  2. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 119334, Moscow, Russian Federation

    I. D. Potapov, M. V. Motyakin & T. D. Nekipelova

  3. N. N. Semenov Federal Research Center of Chemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 119991, Moscow, Russian Federation

    M. V. Motyakin

Authors
  1. I. D. Potapov
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  2. A. Yu. Voznarskiy
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  3. A. V. Mironov
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  4. M. V. Motyakin
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  5. T. D. Nekipelova
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  6. T. A. Podrugina
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Corresponding author

Correspondence to I. D. Potapov.

Additional information

Based on the materials of the All-Russian Congress on Chemistry of Heterocyclic Compounds (October 12–16, 2021, Sochi, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1027–1032, May, 2022.

The work was carried out in the framework of the Russian state assignment No. 121021000105-7.

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Potapov, I.D., Voznarskiy, A.Y., Mironov, A.V. et al. Regioselective heterocyclization of mixed phosphonium-iodonium ylides with acetylenes involving dimethyl acetylenedicarboxylate. Russ Chem Bull 71, 1027–1033 (2022). https://doi.org/10.1007/s11172-022-3504-4

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  • DOI: https://doi.org/10.1007/s11172-022-3504-4

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