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Fluorine-Substituted Arylphosphine for an NHC-Ni(I) System, Air-Stable in a Solid State but Catalytically Active in Solution

Monovalent NHC-nickel complexes bearing triarylphosphine, in which fluorine is incorporated onto the aryl groups, have been synthesized. Tris(3,5-di(trifluoromethyl)-phenyl)phosphine efficiently gave a monovalent nickel bromide complex, whose structure was determined by X-ray diffraction analysis fo...

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Autores principales: Matsubara, Kouki, Fujii, Takahiro, Hosokawa, Rion, Inatomi, Takahiro, Yamada, Yuji, Koga, Yuji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6766797/
https://www.ncbi.nlm.nih.gov/pubmed/31487944
http://dx.doi.org/10.3390/molecules24183222
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author Matsubara, Kouki
Fujii, Takahiro
Hosokawa, Rion
Inatomi, Takahiro
Yamada, Yuji
Koga, Yuji
author_facet Matsubara, Kouki
Fujii, Takahiro
Hosokawa, Rion
Inatomi, Takahiro
Yamada, Yuji
Koga, Yuji
author_sort Matsubara, Kouki
collection PubMed
description Monovalent NHC-nickel complexes bearing triarylphosphine, in which fluorine is incorporated onto the aryl groups, have been synthesized. Tris(3,5-di(trifluoromethyl)-phenyl)phosphine efficiently gave a monovalent nickel bromide complex, whose structure was determined by X-ray diffraction analysis for the first time. In the solid state, the Ni(I) complex was less susceptible to oxidation in air than the triphenylphosphine complex, indicating greatly improved solid-state stability. In contrast, the Ni(I) complex in solution can easily liberate the phosphine, high catalytic activity toward the Kumada–Tamao–Corriu coupling of aryl bromides.
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spelling pubmed-67667972019-10-02 Fluorine-Substituted Arylphosphine for an NHC-Ni(I) System, Air-Stable in a Solid State but Catalytically Active in Solution Matsubara, Kouki Fujii, Takahiro Hosokawa, Rion Inatomi, Takahiro Yamada, Yuji Koga, Yuji Molecules Communication Monovalent NHC-nickel complexes bearing triarylphosphine, in which fluorine is incorporated onto the aryl groups, have been synthesized. Tris(3,5-di(trifluoromethyl)-phenyl)phosphine efficiently gave a monovalent nickel bromide complex, whose structure was determined by X-ray diffraction analysis for the first time. In the solid state, the Ni(I) complex was less susceptible to oxidation in air than the triphenylphosphine complex, indicating greatly improved solid-state stability. In contrast, the Ni(I) complex in solution can easily liberate the phosphine, high catalytic activity toward the Kumada–Tamao–Corriu coupling of aryl bromides. MDPI 2019-09-04 /pmc/articles/PMC6766797/ /pubmed/31487944 http://dx.doi.org/10.3390/molecules24183222 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Matsubara, Kouki
Fujii, Takahiro
Hosokawa, Rion
Inatomi, Takahiro
Yamada, Yuji
Koga, Yuji
Fluorine-Substituted Arylphosphine for an NHC-Ni(I) System, Air-Stable in a Solid State but Catalytically Active in Solution
title Fluorine-Substituted Arylphosphine for an NHC-Ni(I) System, Air-Stable in a Solid State but Catalytically Active in Solution
title_full Fluorine-Substituted Arylphosphine for an NHC-Ni(I) System, Air-Stable in a Solid State but Catalytically Active in Solution
title_fullStr Fluorine-Substituted Arylphosphine for an NHC-Ni(I) System, Air-Stable in a Solid State but Catalytically Active in Solution
title_full_unstemmed Fluorine-Substituted Arylphosphine for an NHC-Ni(I) System, Air-Stable in a Solid State but Catalytically Active in Solution
title_short Fluorine-Substituted Arylphosphine for an NHC-Ni(I) System, Air-Stable in a Solid State but Catalytically Active in Solution
title_sort fluorine-substituted arylphosphine for an nhc-ni(i) system, air-stable in a solid state but catalytically active in solution
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6766797/
https://www.ncbi.nlm.nih.gov/pubmed/31487944
http://dx.doi.org/10.3390/molecules24183222
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