TY - JOUR
T1 - Reaction of elemental phosphorus with α-methylstyrenes
T2 - One-pot synthesis of secondary and tertiary phosphines, prospective bulky ligands for Pd(II) catalysts
AU - Artem'ev, Alexander V.
AU - Malysheva, Svetlana F.
AU - Gusarova, Nina K.
AU - Belogorlova, Nataliya A.
AU - Sukhov, Boris G.
AU - Sutyrina, Anastasiya O.
AU - Matveeva, Elena A.
AU - Vasilevsky, Sergey F.
AU - Govdi, Anastasiya I.
AU - Gatilov, Yuriy V.
AU - Albanov, Alexander I.
AU - Trofimov, Boris A.
PY - 2016/1/28
Y1 - 2016/1/28
N2 -
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.
AB -
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.
KW - Elemental phosphorus
KW - Phosphines
KW - Sonogashira coupling
KW - Superbases
KW - α-Methylstyrene
UR - http://www.scopus.com/inward/record.url?scp=84954196874&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84954196874&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2015.11.009
DO - 10.1016/j.tet.2015.11.009
M3 - Article
AN - SCOPUS:84954196874
VL - 72
SP - 443
EP - 450
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 4
ER -