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Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex
A cross-coupling reaction of allylic aryl ethers with arylmagnesium reagents was investigated using β-aminoketonato- and β-diketiminato-based pincer-type nickel(II) complexes as catalysts. An β-aminoketonato nickel(II) complex bearing a diphenylphosphino group as a third donor effectively catalyzed...
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/PMC6631569/ https://www.ncbi.nlm.nih.gov/pubmed/31234296 http://dx.doi.org/10.3390/molecules24122296 |
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author | Hashimoto, Toru Funatsu, Kei Ohtani, Atsufumi Asano, Erika Yamaguchi, Yoshitaka |
author_facet | Hashimoto, Toru Funatsu, Kei Ohtani, Atsufumi Asano, Erika Yamaguchi, Yoshitaka |
author_sort | Hashimoto, Toru |
collection | PubMed |
description | A cross-coupling reaction of allylic aryl ethers with arylmagnesium reagents was investigated using β-aminoketonato- and β-diketiminato-based pincer-type nickel(II) complexes as catalysts. An β-aminoketonato nickel(II) complex bearing a diphenylphosphino group as a third donor effectively catalyzed the reaction to afford the target cross-coupled products, allylbenzene derivatives, in high yield. The regioselective reaction of a variety of substituted cinnamyl ethers proceeded to give the corresponding linear products. In contrast, α- and γ-alkyl substituted allylic ethers afforded a mixture of the linear and branched products. These results indicated that the coupling reaction proceeded via a π-allyl nickel intermediate. |
format | Online Article Text |
id | pubmed-6631569 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-66315692019-08-19 Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex Hashimoto, Toru Funatsu, Kei Ohtani, Atsufumi Asano, Erika Yamaguchi, Yoshitaka Molecules Article A cross-coupling reaction of allylic aryl ethers with arylmagnesium reagents was investigated using β-aminoketonato- and β-diketiminato-based pincer-type nickel(II) complexes as catalysts. An β-aminoketonato nickel(II) complex bearing a diphenylphosphino group as a third donor effectively catalyzed the reaction to afford the target cross-coupled products, allylbenzene derivatives, in high yield. The regioselective reaction of a variety of substituted cinnamyl ethers proceeded to give the corresponding linear products. In contrast, α- and γ-alkyl substituted allylic ethers afforded a mixture of the linear and branched products. These results indicated that the coupling reaction proceeded via a π-allyl nickel intermediate. MDPI 2019-06-21 /pmc/articles/PMC6631569/ /pubmed/31234296 http://dx.doi.org/10.3390/molecules24122296 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 | Article Hashimoto, Toru Funatsu, Kei Ohtani, Atsufumi Asano, Erika Yamaguchi, Yoshitaka Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex |
title | Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex |
title_full | Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex |
title_fullStr | Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex |
title_full_unstemmed | Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex |
title_short | Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex |
title_sort | cross-coupling reaction of allylic ethers with aryl grignard reagents catalyzed by a nickel pincer complex |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6631569/ https://www.ncbi.nlm.nih.gov/pubmed/31234296 http://dx.doi.org/10.3390/molecules24122296 |
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