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

Capa

Citar

Texto integral

Acesso aberto Acesso aberto
Acesso é fechado Acesso está concedido
Acesso é fechado Acesso é pago ou somente para assinantes

Resumo

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.

Sobre autores

I. Ramazanov

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

Autor responsável pela correspondência
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

Bibliografia

  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.

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
Baixar
2.

Baixar (29KB)
Metadados
3.

Baixar (62KB)
Metadados

Declaração de direitos autorais © И.Р. Рамазанов, Ф.Т. Садыкова, Т.П. Зосим, К.С. Фролова, У.М. Джемилев, 2023