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

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

Journal

Tetrahedron
ISSN: 0040-4020

Output data

Year: 2016, Volume: 72, Number: 4, Pages: 443-450 Pages count : 8 DOI: 10.1016/j.tet.2015.11.009

Tags

Elemental phosphorus; alpha-Methylstyrene; Phosphines; Sonogashira coupling; Superbases

Authors

Artem'ev Alexander V. ¹ , Malysheva Svetlana F. ¹ , Gusarova Nina K. ¹ , Belogorlova Nataliya A. ¹ , Sukhov Boris G. ¹ , Sutyrina Anastasiya O. ¹ , Matveeva Elena A. ¹ , Vasilevsky Sergey F. ^2,3 , Govdi Anastasiya I. ² , Gatilov Yuriy V. ^3,4 , Albanov Alexander I. ¹ , Trofimov Boris A. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, 1 Favorsky Str, Irkutsk 664033, Russia
2	(Данные Web of science) Russian Acad Sci, Inst Chem Kinet & Combust, Siberian Branch, 3 Inst Skaya Str, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, 2 Pirogova Str, Novosibirsk 630090, Russia
4	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Lavrentiev Ave, Novosibirsk 630090, Russia

alpha-Methylstyrene and 4-chloro-alpha-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 degrees 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)(2)C1(2)], which proves to be active in the Sonogashira couplings. (C) 2015 Elsevier Ltd. All rights reserved.

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.
Reaction of elemental phosphorus with alpha-methylstyrenes: one-pot synthesis of secondary and tertiary phosphines, prospective bulky ligands for Pd(II) catalysts
Tetrahedron. 2016. V.72. N4. P.443-450. DOI: 10.1016/j.tet.2015.11.009 WOS Scopus РИНЦ OpenAlex

Published print:

Jan 1, 2016

Web of science:	WOS:000368868200001
Scopus:	2-s2.0-84954196874
Elibrary:	26947415
OpenAlex:	W2191656595

DB	Citing
Web of science	16
Scopus	18
Elibrary	21
OpenAlex	18