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Visible light photoredox-catalyzed deoxygenation of alcohols

Carbon–oxygen single bonds are ubiquitous in natural products whereas efficient methods for their reductive defunctionalization are rare. In this work an environmentally benign protocol for the activation of carbon–oxygen single bonds of alcohols towards a reductive bond cleavage under visible light...

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Autores principales: Rackl, Daniel, Kais, Viktor, Kreitmeier, Peter, Reiser, Oliver
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168922/
https://www.ncbi.nlm.nih.gov/pubmed/25246974
http://dx.doi.org/10.3762/bjoc.10.223
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author Rackl, Daniel
Kais, Viktor
Kreitmeier, Peter
Reiser, Oliver
author_facet Rackl, Daniel
Kais, Viktor
Kreitmeier, Peter
Reiser, Oliver
author_sort Rackl, Daniel
collection PubMed
description Carbon–oxygen single bonds are ubiquitous in natural products whereas efficient methods for their reductive defunctionalization are rare. In this work an environmentally benign protocol for the activation of carbon–oxygen single bonds of alcohols towards a reductive bond cleavage under visible light photocatalysis was developed. Alcohols were activated as 3,5-bis(trifluoromethyl)-substituted benzoates and irradiation with blue light in the presence of [Ir(ppy)(2)(dtb-bpy)](PF(6)) as visible light photocatalyst and Hünig’s base as sacrificial electron donor in an acetonitrile/water mixture generally gave good to excellent yields of the desired defunctionalized compounds. Functional group tolerance is high but the protocol developed is limited to benzylic, α-carbonyl, and α-cyanoalcohols; with other alcohols a slow partial C–F bond reduction in the 3,5-bis(trifluoromethyl)benzoate moiety occurs.
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spelling pubmed-41689222014-09-22 Visible light photoredox-catalyzed deoxygenation of alcohols Rackl, Daniel Kais, Viktor Kreitmeier, Peter Reiser, Oliver Beilstein J Org Chem Full Research Paper Carbon–oxygen single bonds are ubiquitous in natural products whereas efficient methods for their reductive defunctionalization are rare. In this work an environmentally benign protocol for the activation of carbon–oxygen single bonds of alcohols towards a reductive bond cleavage under visible light photocatalysis was developed. Alcohols were activated as 3,5-bis(trifluoromethyl)-substituted benzoates and irradiation with blue light in the presence of [Ir(ppy)(2)(dtb-bpy)](PF(6)) as visible light photocatalyst and Hünig’s base as sacrificial electron donor in an acetonitrile/water mixture generally gave good to excellent yields of the desired defunctionalized compounds. Functional group tolerance is high but the protocol developed is limited to benzylic, α-carbonyl, and α-cyanoalcohols; with other alcohols a slow partial C–F bond reduction in the 3,5-bis(trifluoromethyl)benzoate moiety occurs. Beilstein-Institut 2014-09-10 /pmc/articles/PMC4168922/ /pubmed/25246974 http://dx.doi.org/10.3762/bjoc.10.223 Text en Copyright © 2014, Rackl et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Rackl, Daniel
Kais, Viktor
Kreitmeier, Peter
Reiser, Oliver
Visible light photoredox-catalyzed deoxygenation of alcohols
title Visible light photoredox-catalyzed deoxygenation of alcohols
title_full Visible light photoredox-catalyzed deoxygenation of alcohols
title_fullStr Visible light photoredox-catalyzed deoxygenation of alcohols
title_full_unstemmed Visible light photoredox-catalyzed deoxygenation of alcohols
title_short Visible light photoredox-catalyzed deoxygenation of alcohols
title_sort visible light photoredox-catalyzed deoxygenation of alcohols
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168922/
https://www.ncbi.nlm.nih.gov/pubmed/25246974
http://dx.doi.org/10.3762/bjoc.10.223
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