Reaction of elemental phosphorus with α-methylstyrenes: One-pot synthesis of secondary and tertiary phosphines, prospective bulky ligands for Pd(II) catalysts

Alexander V. Artem'ev, Svetlana F. Malysheva, Nina K. Gusarova, Nataliya A. Belogorlova, Boris G. Sukhov, Anastasiya O. Sutyrina, Elena A. Matveeva, Sergey F. Vasilevsky, Anastasiya I. Govdi, Yuriy V. Gatilov, Alexander I. Albanov, Boris A. Trofimov

Результат исследований: Материалы для журналаСтатья

11 Цитирования (Scopus)

Аннотация

α-Methylstyrene and 4-chloro-α-methylstyrene react readily with elemental (red) phosphorus under microwave-irradiation in the superbase KOH/DMSO suspension to afford, depending on the reactant ratio and reaction time, either corresponding bis(2-arylpropyl)phosphines or tris(2-arylpropyl)phosphines in 46-54% and 69-77% yields, respectively. Upon the heating only (110-130 °C, 3 h), this reaction provides mainly tris(2-arylpropyl)phosphine oxides (up to 78% yield) along with (2-arylpropyl)phosphinic acids (up to 43%). The synthesized phosphines are prospective bulky ligands for metal catalysts that has been demonstrated by the preparation of a new Pd(II) complex, trans-[Pd(PR 3 ) 2 Cl 2 ], which proves to be active in the Sonogashira couplings.

Язык оригиналаАнглийский
Страницы (с-по)443-450
Число страниц8
ЖурналTetrahedron
Том72
Номер выпуска4
DOI
СостояниеОпубликовано - 28 янв 2016
Опубликовано для внешнего пользованияДа

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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  • Цитировать

    Artem'ev, A. V., Malysheva, S. F., Gusarova, N. K., Belogorlova, N. A., Sukhov, B. G., Sutyrina, A. O., Matveeva, E. A., Vasilevsky, S. F., Govdi, A. I., Gatilov, Y. V., Albanov, A. I., & Trofimov, B. A. (2016). Reaction of elemental phosphorus with α-methylstyrenes: One-pot synthesis of secondary and tertiary phosphines, prospective bulky ligands for Pd(II) catalysts. Tetrahedron, 72(4), 443-450. https://doi.org/10.1016/j.tet.2015.11.009