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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...

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Autores principales: Tobisu, Mamoru, Morioka, Toshifumi, Ohtsuki, Akimichi, Chatani, Naoto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
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.
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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
title_full Nickel-catalyzed reductive cleavage of aryl alkyl ethers to arenes in absence of external reductant
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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AT ohtsukiakimichi nickelcatalyzedreductivecleavageofarylalkyletherstoarenesinabsenceofexternalreductant
AT chataninaoto nickelcatalyzedreductivecleavageofarylalkyletherstoarenesinabsenceofexternalreductant