ACTIVATING EFFECT OF AlCl3 IN HOMO-COUPLING REACTION OF ACETYLENE COMPOUNDS UNDER THE ACTION OF Mg–Cp2ZrCl2 REAGENT SYSTEMS

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详细

The activating effect of AlCl3 in the amount of 10 mol. % in the homo-coupling of alkyl-, phenyl-, and silyl-substituted acetylenes with the Mg–Cp2ZrCl2 reagent system was found for the first time. The unique nature of this activation is indicated by the fact that in the presence of 10 mol. % of Lewis acids such as BF3 ⋅ Et2O, Me3SiCl, InCl3, and SnCl4, the reaction with 5-decyne does not occur even after 5 h, while in the presence of AlCl3, homocoupling products are selectively formed in high yield in 10 min at room temperature.

作者简介

I. Ramazanov

Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences

编辑信件的主要联系方式.
Email: ilfir.ramazanov@gmail.com
Russian Federation, 450075, Ufa

F. Sadykova

Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences

Email: ilfir.ramazanov@gmail.com
Russian Federation, 450075, Ufa

T. Zosim

Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences

Email: ilfir.ramazanov@gmail.com
Russian Federation, 450075, Ufa

K. Frolova

Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences

Email: ilfir.ramazanov@gmail.com
Russian Federation, 450075, Ufa

U. Dzhemilev

N.D. Zelinsky Institute of Organic Chemistry of Russian Academy of Sciences

Email: ilfir.ramazanov@gmail.com
Russian Federation, 119991, Moscow

参考

  1. Negishi E., Holmes S.J., Tour J.M., Miller J.A., Cederbaum F.E., Swanson D.R., Takahashi T. // J. Am. Chem. Soc. 1989. V. 111. P. 3336–3346. https://doi.org/10.1021/ja00191a035
  2. Negishi E. // Dalton Trans. 2005. P. 827–848. https://doi.org/10.1039/B417134A
  3. Negishi E., Cederbaum F.E., Takahashi T. // Tetrahedron Lett. 1986. V. 27. P. 2829–2832. https://doi.org/10.1016/S0040-4039(00)84653-5
  4. Urrego-Riveros S., Ramirez y Medina I., Duvinage D., Lork E., Sönnichsen F.D., Staubitz A. // Chem. – Eur. J. 2019. V. 25. P. 13318–13328. https://doi.org/10.1002/chem.201902255
  5. Linshoeft J. // Synlett. 2014. V. 25. P. 2671–2672. https://doi.org/10.1055/s-0034-1379317
  6. Rosenthal U., Burlakov V.V. Organometallic chemistry of titanocene and zirconocene complexes with bis (trimethylsilyl) acetylene as the basis for applications in organic synthesis. In: Titanium and Zirconium in Organic Synthesis. Marek I. (Ed.). Wiley-VCH Verlag GmbH & Co. KGaA, 2002. P. 355–389. https://doi.org/10.1002/3527600671.ch10
  7. Sato F., Urabe H., Okamoto S. // Synlett. 2000. V. 2000. P. 753–775. https://doi.org/10.1055/s-2000-6689
  8. Kulinkovich O.G., Sviridov S.V., Vasilevski D.A. // Synthesis. 1991. V. 1991. P. 234. https://doi.org/10.1055/s-1991-26431
  9. Negishi E.-i., Kondakov D.Y., Choueiry Danièle, Kasai K., Takahashi T. // J. Am. Chem. Soc. 1996. V. 118. P. 9577–9588. https://doi.org/10.1021/ja9538039
  10. Dyakonov V.A. Dzhemilev reactions in organic and organometallic synthesis. NOVA Sci. Publ.: New York, 2010. 96 p.
  11. Abakumov G.A., Piskunov A.V., Cherkasov V.K., Fedushkin I.L., Ananikov V.P., Eremin D.B., Gordeev E.G., Beletskaya I.P., Averin A.D., Bochkarev M.N., Trifo-nov A.A., Dzhemilev U.M., D’yakonov V.A., Egorov M.P., Vereshchagin A.N., Syroeshkin M.A., Jouikov V.V., Muzafarov A.M., Anisimov A.A., Arzumanyan A.V., Kono-nevich Yu.N., Temnikov M.N., Sinyashin O.G., Budnikova Yu.H., Burilov A.R., Karasik A.A., Mironov V.F., Storozhenko P.A., Shcherbakova G.I., Trofimov B.A., Amosova S.V., Gusarova N.K., Potapov V.A., Shur V.B., Burlakov V.V., Bogdanov V.S., Andreev M.V. // Russ. Chem. Rev. 2018. V. 87. P. 393–507. https://doi.org/10.1070/RCR4795
  12. Islamov I.I., Makarov A.A., Makarova E.Kh., Yusu-pova A.V., D’yakonov V.A., Dzhemilev U.M. // Russ. Chem. Bull. 2023. V. 72. P. 925–931. https://doi.org/10.1007/s11172-023-3855-1
  13. Dzhemilev U.M., Ibragimov A.G. // Russ. Chem. Rev. 2000. V. 69. P. 121–135. https://doi.org/10.1070/RC2000v069n02ABEH000519
  14. Ramazanov I.R., Kadikova R.N., Amirova A.K., Dzhemilev U.M. // Dokl. Chem. 2020. V. 494. P. 155–158. https://doi.org/10.1134/S0012500820100031
  15. Negishi E.-i. // Chem. – Eur. J. 1999. V. 5. P. 411–420. https://doi.org/10.1002/(SICI)1521-3765(19990201)5:2<411::AID-CHEM411>3.0.CO;2-H
  16. Takahashi T., Li Y. Zirconacyclopentadienes in organic synthesis. In: Titanium and Zirconium in Organic Synthesis. Marek I. (Ed.). Wiley-VCH Verlag GmbH & Co. KGaA, 2002. P. 50–85. https://doi.org/10.1002/3527600671.ch2
  17. Dzhemilev U.M., Ibragimov A.G., D’yakonov V.A., Zinnurova R.A. // Russ. J. Org. Chem. 2007. V. 43. P. 176–180. https://doi.org/10.1134/S1070428007020030
  18. Ramazanov I.R., Kadikova R.N., Amirova A.K., Mozgovoj O.S., Dzhemilev U.M. // RSC Adv. 2021. V. 11. P. 39518–39522. https://doi.org/10.1039/D1RA08268J
  19. Xi Z., Liu X., Lu J., Bao F., Fan H., Li Z., Takahashi T. // J. Org. Chem. 2004. V. 69. P. 8547–8549. https://doi.org/10.1021/jo048940f
  20. Brandsma L., Verkruijsse H.D. Synthesis of acetylenes, allenes, cumulenes: A laboratory manual. Elsevier Science Pub. Co., Amsterdam–New York, 1981. 276 p.

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版权所有 © И.Р. Рамазанов, Ф.Т. Садыкова, Т.П. Зосим, К.С. Фролова, У.М. Джемилев, 2023