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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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2019
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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. |
format | Online Article Text |
id | pubmed-6766797 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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