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 журнала › Статья › рецензирование

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 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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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

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 › рецензирование

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",

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

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pages = "443--450",

journal = "Tetrahedron",

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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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