Reaction of elemental phosphorus with α-methylstyrenes: one-pot synthesis of secondary and tertiary phosphines, prospective bulky ligands for Pd(II) catalysts
2016
Artem'ev, Alexander V. | Malysheva, Svetlana F. | Gusarova, Nina K. | Belogorlova, Nataliya A. | Sukhov, Boris G. | Sutyrina, Anastasiya O. | Matveeva, Elena A. | Vasilevsky, Sergey F. | Govdi, Anastasiya I. | Gatilov, Yuriy V. | Albanov, Alexander I. | Trofimov, Boris A.
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(PR3)2Cl2], which proves to be active in the Sonogashira couplings.
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