Unexpectedly easy non-catalytic transfer of allyl group from allyl sulfides to secondary phosphine sulfides

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The unexpected allylation of secondary phosphine sulfides with allyl sulfides has been found. The reaction proceeds under mild conditions (no catalyst and solvent, 80°C) to give allyldiorganylphosphine sulfides (yield up to 79%). The latter, under the reaction conditions, are able to add the initial secondary phosphine sulfides across the allyl group in the anti-Markovnikov mode to deliver propane-1,3-diylbis(diorganylphosphine sulfides), promising extractants of heavy metals and ligands for the synthesis of metal complex catalysts.

作者简介

N. Chernysheva

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: boris_trofimov@irioch.irk.ru

S. Verkhoturova

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: boris_trofimov@irioch.irk.ru

A. Nalibayeva

D.V. Sokolskiy Institute of Fuel, Catalysis and Electrochemistry

Email: boris_trofimov@irioch.irk.ru

G. Bishimbayeva

D.V. Sokolskiy Institute of Fuel, Catalysis and Electrochemistry

Email: boris_trofimov@irioch.irk.ru

S. Arbuzova

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: boris_trofimov@irioch.irk.ru

S. Zinchenko

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: boris_trofimov@irioch.irk.ru

B. Trofimov

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

Email: boris_trofimov@irioch.irk.ru

参考

  1. Leca D., Fensterbank L., Lacôte E., Malacria M. Chem. Soc. Rev. 2005, 34, 858-865. doi: 10.1039/b500511f
  2. Ananikov V.P., Khemchyan L.L., Beletskaya I.P. Synlett. 2009, 2375-2381. doi: 10.1055/s-0029-1217739
  3. Malysheva S.F., Gusarova N.K., Artem'ev A.V., Belogorlova N.A., Albanov A.I., Borodina T.N., Smirnov V.I., Trofimov B.A. Eur. J. Org. Chem. 2014, 2516-2521. doi: 10.1002/ejoc.201301786
  4. Moglie Y., González-Soria M.J., Martín-García I., Radivoy G., Alonso F. Green Chem. 2016, 18, 4896-4907. doi: 10.1039/C6GC00903D
  5. Gusarova N.K., Chernysheva N.A., Trofimov B.A. Synthesis. 2017, 49, 4783-4807. doi: 10.1055/s-0036-1588542
  6. Nájera C., Beletskaya I.P., Yus M. Chem. Soc. Rev. 2019, 48, 4515-4618. doi: 10.1039/C8CS00872H
  7. Гусарова Н.К., Трофимов Б.А. Усп. хим. 2020, 89. 225-249.
  8. Gusarova N.K., Trofimov B.A. Russ. Chem. Rev. 2020, 89, 225-249. doi: 10.1070/RCR4903
  9. Tran D.Ph., Sato Y., Yamamoto Y., Kawaguchi Sh., Kodama Sh., Nomoto A., Ogawa A. Res. Chem. Intermed. 2021, 47, 3067-3078. doi: 10.1007/s11164-021-04433-7
  10. Nouri A., Zahedi E., Ehsani M., Nouri A., Balali E. J. Sulf. Chem. 2018, 39, 350-366. doi: 10.1080/17415993.2018.1428746
  11. Osakada K. Matsumoto K., Yamamoto T., Yamamoto A. Organometallics. 1985, 4, 857-862. doi: 10.1021/om00124a010
  12. Меньшиков В.И., Воронова И.Ю., Пройдакова О.А., Малышева С.Ф., Иванова Н.И., Белогорлова Н.А., Гусарова Н.К., Трофимов Б.А. ЖПХ. 2009, 82, 189-195.
  13. Men'shikov V.I., Voronova I.Y., Proidakova O.A., Malysheva S.F., Ivanova N.I., Belogorlova N.A., Gusarova N.K., Trofimov B.A. Russ. J. Appl. Chem. 2009, 82, 183-189. doi: 10.1134/S1070427209020025
  14. Bessen N.P., Jackson J.A., Jensen M.P., Shafer J.C. Coord. Chem. Rev. 2020, 421, Article 213446. doi: 10.1016/j.ccr.2020.213446
  15. Subasi E., Senturk O.S., Ugur F.Z. Naturforsch. 2004, 59b, 836-838.
  16. Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis. Eds. P.CJ. Kamer, P.W.N.M. van Leeuwen. Chichester: John Wiley & Sons. 2012.
  17. Goda K., Hanafusa F., Inamoto N. Bull. Chem. Soc. Jap. 1978, 51, 818-820. doi: 10.1246/bcsj.51.818
  18. Дроздова Я.А., Бурилов А.Р., Пудовик М.А. Изв. АН. Сер. Хим. 1993, 42, 1441-1443.
  19. Drozdova Ya.A., Burilov A.R., Pudovik M.A. Izv. Akad. Nauk, Ser. Khim. 1993, 42, 1377-1379. doi: 10.1007/BF00699935
  20. Kosolapoff G.M., Maier L. Organic Phosphorus Compounds. N.Y.-London-Sydney-Toronto: Wiley-Intersci. 1972, 4, 40.
  21. Postle S.R. Phosphorus, Sulfur Silicon Relat. Elem. 1977, 3, 269-275. doi: 10.1080/03086647708079933
  22. Trofimov B.A., Brandsma L., Arbuzova S.N., Malysheva S.F., Gusarova N.K. Tetrahedron Lett. 1994, 35, 7647-7650. doi: 10.1016/S0040-4039(00)78365-1

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