A new access to tri(1-naphthyl)phosphine and its catalytically active palladacycles and luminescent Cu(I) complex

Alexander V. Artem'ev, Vladimir A. Kuimov, Elena A. Matveeva, Irina Yu Bagryanskaya, Anastasia I. Govdi, Sergey F. Vasilevsky, Mariana I. Rakhmanova, Dmitry O. Samultsev, Nina K. Gusarova, Boris A. Trofimov

Research output: Contribution to journalArticleResearchpeer-review

3 Citations (Scopus)

Abstract

New approach to synthesis of tri(1-naphthyl)phosphine (Np 3 P) and its application for design of new Pd(II) and Cu(I) complexes are reported. This phosphine has been prepared in 32% yield through exhaustive P–H arylation of РН 3 with 1-chloronaphthalene in the superbasic t-BuOK/DMSO system at 70 °C. The Np 3 P was found to readily reacts with chloro-bridged dimers, [(κ 2 -C,N)Pd(μ-Cl)] 22 -C,N = PhCH 2 NMe 2 (2a) or FcCH 2 NMe 2 (2b), to give new mononuclear palladacycles [(κ 2 -C,N)Pd(Np 3 P)Cl] (3, 4), in which metal has a square-planar geometry. These complexes show good catalytic activity in the Sonogashira reaction under low catalyst loadings (2 mol% Pd) and relatively mild conditions. We also synthesized and characterized first Cu(I) complex with Np 3 P, namely, [Cu(phen)(Np 3 P)I], that exhibits red emission (λ max = 650 nm) at room temperature.

Original languageEnglish
Pages (from-to)94-97
Number of pages4
JournalInorganic Chemistry Communications
Volume86
DOIs
StatePublished - 1 Dec 2017

Keywords

  • Copper(I)
  • Luminescence
  • Palladacycles
  • Phosphine
  • Sonogashira coupling
  • Tri(1-naphthyl)phosphine

Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Artem'ev, Alexander V. ; Kuimov, Vladimir A. ; Matveeva, Elena A. ; Bagryanskaya, Irina Yu ; Govdi, Anastasia I. ; Vasilevsky, Sergey F. ; Rakhmanova, Mariana I. ; Samultsev, Dmitry O. ; Gusarova, Nina K. ; Trofimov, Boris A. / A new access to tri(1-naphthyl)phosphine and its catalytically active palladacycles and luminescent Cu(I) complex. In: Inorganic Chemistry Communications. 2017 ; Vol. 86. pp. 94-97.
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title = "A new access to tri(1-naphthyl)phosphine and its catalytically active palladacycles and luminescent Cu(I) complex",
abstract = "New approach to synthesis of tri(1-naphthyl)phosphine (Np 3 P) and its application for design of new Pd(II) and Cu(I) complexes are reported. This phosphine has been prepared in 32{\%} yield through exhaustive P–H arylation of РН 3 with 1-chloronaphthalene in the superbasic t-BuOK/DMSO system at 70 °C. The Np 3 P was found to readily reacts with chloro-bridged dimers, [(κ 2 -C,N)Pd(μ-Cl)] 2 (κ 2 -C,N = PhCH 2 NMe 2 (2a) or FcCH 2 NMe 2 (2b), to give new mononuclear palladacycles [(κ 2 -C,N)Pd(Np 3 P)Cl] (3, 4), in which metal has a square-planar geometry. These complexes show good catalytic activity in the Sonogashira reaction under low catalyst loadings (2 mol{\%} Pd) and relatively mild conditions. We also synthesized and characterized first Cu(I) complex with Np 3 P, namely, [Cu(phen)(Np 3 P)I], that exhibits red emission (λ max = 650 nm) at room temperature.",
keywords = "Copper(I), Luminescence, Palladacycles, Phosphine, Sonogashira coupling, Tri(1-naphthyl)phosphine",
author = "Artem'ev, {Alexander V.} and Kuimov, {Vladimir A.} and Matveeva, {Elena A.} and Bagryanskaya, {Irina Yu} and Govdi, {Anastasia I.} and Vasilevsky, {Sergey F.} and Rakhmanova, {Mariana I.} and Samultsev, {Dmitry O.} and Gusarova, {Nina K.} and Trofimov, {Boris A.}",
year = "2017",
month = "12",
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doi = "10.1016/j.inoche.2017.09.008",
language = "English",
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Artem'ev, AV, Kuimov, VA, Matveeva, EA, Bagryanskaya, IY, Govdi, AI, Vasilevsky, SF, Rakhmanova, MI, Samultsev, DO, Gusarova, NK & Trofimov, BA 2017, 'A new access to tri(1-naphthyl)phosphine and its catalytically active palladacycles and luminescent Cu(I) complex' Inorganic Chemistry Communications, vol. 86, pp. 94-97. https://doi.org/10.1016/j.inoche.2017.09.008

A new access to tri(1-naphthyl)phosphine and its catalytically active palladacycles and luminescent Cu(I) complex. / Artem'ev, Alexander V.; Kuimov, Vladimir A.; Matveeva, Elena A.; Bagryanskaya, Irina Yu; Govdi, Anastasia I.; Vasilevsky, Sergey F.; Rakhmanova, Mariana I.; Samultsev, Dmitry O.; Gusarova, Nina K.; Trofimov, Boris A.

In: Inorganic Chemistry Communications, Vol. 86, 01.12.2017, p. 94-97.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - A new access to tri(1-naphthyl)phosphine and its catalytically active palladacycles and luminescent Cu(I) complex

AU - Artem'ev, Alexander V.

AU - Kuimov, Vladimir A.

AU - Matveeva, Elena A.

AU - Bagryanskaya, Irina Yu

AU - Govdi, Anastasia I.

AU - Vasilevsky, Sergey F.

AU - Rakhmanova, Mariana I.

AU - Samultsev, Dmitry O.

AU - Gusarova, Nina K.

AU - Trofimov, Boris A.

PY - 2017/12/1

Y1 - 2017/12/1

N2 - New approach to synthesis of tri(1-naphthyl)phosphine (Np 3 P) and its application for design of new Pd(II) and Cu(I) complexes are reported. This phosphine has been prepared in 32% yield through exhaustive P–H arylation of РН 3 with 1-chloronaphthalene in the superbasic t-BuOK/DMSO system at 70 °C. The Np 3 P was found to readily reacts with chloro-bridged dimers, [(κ 2 -C,N)Pd(μ-Cl)] 2 (κ 2 -C,N = PhCH 2 NMe 2 (2a) or FcCH 2 NMe 2 (2b), to give new mononuclear palladacycles [(κ 2 -C,N)Pd(Np 3 P)Cl] (3, 4), in which metal has a square-planar geometry. These complexes show good catalytic activity in the Sonogashira reaction under low catalyst loadings (2 mol% Pd) and relatively mild conditions. We also synthesized and characterized first Cu(I) complex with Np 3 P, namely, [Cu(phen)(Np 3 P)I], that exhibits red emission (λ max = 650 nm) at room temperature.

AB - New approach to synthesis of tri(1-naphthyl)phosphine (Np 3 P) and its application for design of new Pd(II) and Cu(I) complexes are reported. This phosphine has been prepared in 32% yield through exhaustive P–H arylation of РН 3 with 1-chloronaphthalene in the superbasic t-BuOK/DMSO system at 70 °C. The Np 3 P was found to readily reacts with chloro-bridged dimers, [(κ 2 -C,N)Pd(μ-Cl)] 2 (κ 2 -C,N = PhCH 2 NMe 2 (2a) or FcCH 2 NMe 2 (2b), to give new mononuclear palladacycles [(κ 2 -C,N)Pd(Np 3 P)Cl] (3, 4), in which metal has a square-planar geometry. These complexes show good catalytic activity in the Sonogashira reaction under low catalyst loadings (2 mol% Pd) and relatively mild conditions. We also synthesized and characterized first Cu(I) complex with Np 3 P, namely, [Cu(phen)(Np 3 P)I], that exhibits red emission (λ max = 650 nm) at room temperature.

KW - Copper(I)

KW - Luminescence

KW - Palladacycles

KW - Phosphine

KW - Sonogashira coupling

KW - Tri(1-naphthyl)phosphine

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U2 - 10.1016/j.inoche.2017.09.008

DO - 10.1016/j.inoche.2017.09.008

M3 - Article

VL - 86

SP - 94

EP - 97

JO - Inorganic Chemistry Communication

JF - Inorganic Chemistry Communication

SN - 1387-7003

ER -