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Nickel-catalyzed reductive cleavage of aryl alkyl ethers to arenes in absence of external reductant
The reductive cleavage of the C–O bonds of aryl ethers has great potential in organic synthesis. Although several catalysts that can promote the reductive cleavage of aryl ethers have been reported, all such systems require the use of an external reductant, e.g., hydrosilane or hydrogen. Here, we re...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Royal Society of Chemistry
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5659071/ https://www.ncbi.nlm.nih.gov/pubmed/29511506 http://dx.doi.org/10.1039/c5sc00305a |
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author | Tobisu, Mamoru Morioka, Toshifumi Ohtsuki, Akimichi Chatani, Naoto |
author_facet | Tobisu, Mamoru Morioka, Toshifumi Ohtsuki, Akimichi Chatani, Naoto |
author_sort | Tobisu, Mamoru |
collection | PubMed |
description | The reductive cleavage of the C–O bonds of aryl ethers has great potential in organic synthesis. Although several catalysts that can promote the reductive cleavage of aryl ethers have been reported, all such systems require the use of an external reductant, e.g., hydrosilane or hydrogen. Here, we report the development of a new nickel-based catalytic system that can cleave the C–O bonds of ethers in the absence of an external reductant. The hydrogen atom required in this new reductive cleavage reaction is provided by the alkoxy group of the substrate, which serves as an internal reductant. The absence of an external reductant enables the unique chemoselectivity, i.e., the selective reduction of an alkoxy group over alkenes and ketones. |
format | Online Article Text |
id | pubmed-5659071 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-56590712018-03-06 Nickel-catalyzed reductive cleavage of aryl alkyl ethers to arenes in absence of external reductant Tobisu, Mamoru Morioka, Toshifumi Ohtsuki, Akimichi Chatani, Naoto Chem Sci Chemistry The reductive cleavage of the C–O bonds of aryl ethers has great potential in organic synthesis. Although several catalysts that can promote the reductive cleavage of aryl ethers have been reported, all such systems require the use of an external reductant, e.g., hydrosilane or hydrogen. Here, we report the development of a new nickel-based catalytic system that can cleave the C–O bonds of ethers in the absence of an external reductant. The hydrogen atom required in this new reductive cleavage reaction is provided by the alkoxy group of the substrate, which serves as an internal reductant. The absence of an external reductant enables the unique chemoselectivity, i.e., the selective reduction of an alkoxy group over alkenes and ketones. Royal Society of Chemistry 2015-06-01 2015-03-27 /pmc/articles/PMC5659071/ /pubmed/29511506 http://dx.doi.org/10.1039/c5sc00305a Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by-nc/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Chemistry Tobisu, Mamoru Morioka, Toshifumi Ohtsuki, Akimichi Chatani, Naoto Nickel-catalyzed reductive cleavage of aryl alkyl ethers to arenes in absence of external reductant |
title | Nickel-catalyzed reductive cleavage of aryl alkyl ethers to arenes in absence of external reductant
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title_full | Nickel-catalyzed reductive cleavage of aryl alkyl ethers to arenes in absence of external reductant
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title_fullStr | Nickel-catalyzed reductive cleavage of aryl alkyl ethers to arenes in absence of external reductant
|
title_full_unstemmed | Nickel-catalyzed reductive cleavage of aryl alkyl ethers to arenes in absence of external reductant
|
title_short | Nickel-catalyzed reductive cleavage of aryl alkyl ethers to arenes in absence of external reductant
|
title_sort | nickel-catalyzed reductive cleavage of aryl alkyl ethers to arenes in absence of external reductant |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5659071/ https://www.ncbi.nlm.nih.gov/pubmed/29511506 http://dx.doi.org/10.1039/c5sc00305a |
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