Photocatalytic carbanion generation from C–H bonds – reductant free Barbier/Grignard-type reactions

We report a redox-neutral method for the generation of carbanions from benzylic C–H bonds in a photocatalytic Grignard-type reaction. The combination of photo- and hydrogen atom transfer (HAT) catalysis enables the abstraction of a benzylic hydrogen atom, generating a radical intermediate. This radi...

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Detalles Bibliográficos
Autores principales: Berger, Anna Lucia, Donabauer, Karsten, König, Burkhard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8133029/
https://www.ncbi.nlm.nih.gov/pubmed/34040714
http://dx.doi.org/10.1039/c9sc04987h
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author Berger, Anna Lucia
Donabauer, Karsten
König, Burkhard
author_facet Berger, Anna Lucia
Donabauer, Karsten
König, Burkhard
author_sort Berger, Anna Lucia
collection PubMed
description We report a redox-neutral method for the generation of carbanions from benzylic C–H bonds in a photocatalytic Grignard-type reaction. The combination of photo- and hydrogen atom transfer (HAT) catalysis enables the abstraction of a benzylic hydrogen atom, generating a radical intermediate. This radical is reduced in situ by the organic photocatalyst to a carbanion, which is able to react with electrophiles such as aldehydes or ketones, yielding homobenzylic secondary and tertiary alcohols.
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spelling pubmed-81330292021-05-25 Photocatalytic carbanion generation from C–H bonds – reductant free Barbier/Grignard-type reactions Berger, Anna Lucia Donabauer, Karsten König, Burkhard Chem Sci Chemistry We report a redox-neutral method for the generation of carbanions from benzylic C–H bonds in a photocatalytic Grignard-type reaction. The combination of photo- and hydrogen atom transfer (HAT) catalysis enables the abstraction of a benzylic hydrogen atom, generating a radical intermediate. This radical is reduced in situ by the organic photocatalyst to a carbanion, which is able to react with electrophiles such as aldehydes or ketones, yielding homobenzylic secondary and tertiary alcohols. The Royal Society of Chemistry 2019-11-12 /pmc/articles/PMC8133029/ /pubmed/34040714 http://dx.doi.org/10.1039/c9sc04987h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Berger, Anna Lucia
Donabauer, Karsten
König, Burkhard
Photocatalytic carbanion generation from C–H bonds – reductant free Barbier/Grignard-type reactions
title Photocatalytic carbanion generation from C–H bonds – reductant free Barbier/Grignard-type reactions
title_full Photocatalytic carbanion generation from C–H bonds – reductant free Barbier/Grignard-type reactions
title_fullStr Photocatalytic carbanion generation from C–H bonds – reductant free Barbier/Grignard-type reactions
title_full_unstemmed Photocatalytic carbanion generation from C–H bonds – reductant free Barbier/Grignard-type reactions
title_short Photocatalytic carbanion generation from C–H bonds – reductant free Barbier/Grignard-type reactions
title_sort photocatalytic carbanion generation from c–h bonds – reductant free barbier/grignard-type reactions
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8133029/
https://www.ncbi.nlm.nih.gov/pubmed/34040714
http://dx.doi.org/10.1039/c9sc04987h
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AT konigburkhard photocatalyticcarbaniongenerationfromchbondsreductantfreebarbiergrignardtypereactions

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