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

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 оригинала	Английский
Страницы (с-по)	443-450
Число страниц	8
Журнал	Tetrahedron
Том	72
Номер выпуска	4
DOI	https://doi.org/10.1016/j.tet.2015.11.009
Состояние	Опубликовано - 28 янв 2016
Опубликовано для внешнего пользования	Да

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Доступ к документу

10.1016/j.tet.2015.11.009

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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

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

В: Tetrahedron, Том 72, № 4, 28.01.2016, стр. 443-450.

Результат исследований: Материалы для журнала › Статья

Artem'ev, AV, Malysheva, SF, Gusarova, NK, Belogorlova, NA, Sukhov, BG, Sutyrina, AO, Matveeva, EA, Vasilevsky, SF, Govdi, AI, Gatilov, YV, Albanov, AI & Trofimov, BA 2016, 'Reaction of elemental phosphorus with α-methylstyrenes: One-pot synthesis of secondary and tertiary phosphines, prospective bulky ligands for Pd(II) catalysts', Tetrahedron, том. 72, № 4, стр. 443-450. https://doi.org/10.1016/j.tet.2015.11.009

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. / Reaction of elemental phosphorus with α-methylstyrenes : One-pot synthesis of secondary and tertiary phosphines, prospective bulky ligands for Pd(II) catalysts. В: Tetrahedron. 2016 ; Том 72, № 4. стр. 443-450.

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

abstract = " 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. ",

keywords = "Elemental phosphorus, Phosphines, Sonogashira coupling, Superbases, α-Methylstyrene",

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

year = "2016",

month = jan,

day = "28",

doi = "10.1016/j.tet.2015.11.009",

language = "English",

volume = "72",

pages = "443--450",

journal = "Tetrahedron",

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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

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