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Atropoenantioselective palladaelectro-catalyzed anilide C–H olefinations viable with natural sunlight as sustainable power source

Enantioselective electrocatalyzed transformations represent a major challenge. We herein achieved atropoenantioselective pallada-electrocatalyzed C–H olefinations and C–H allylations with high efficacy and enantioselectivity under exceedingly mild reaction conditions. With (S)-5-oxoproline as the ch...

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Detalles Bibliográficos
Autores principales: Frey, Johanna, Hou, Xiaoyan, Ackermann, Lutz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8890107/
https://www.ncbi.nlm.nih.gov/pubmed/35340853
http://dx.doi.org/10.1039/d1sc06135f
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author Frey, Johanna
Hou, Xiaoyan
Ackermann, Lutz
author_facet Frey, Johanna
Hou, Xiaoyan
Ackermann, Lutz
author_sort Frey, Johanna
collection PubMed
description Enantioselective electrocatalyzed transformations represent a major challenge. We herein achieved atropoenantioselective pallada-electrocatalyzed C–H olefinations and C–H allylations with high efficacy and enantioselectivity under exceedingly mild reaction conditions. With (S)-5-oxoproline as the chiral ligand, activated and non-activated olefins were suitable substrates for the electro-C–H activations. Dual catalysis was devised in terms of electro-C–H olefination, along with catalytic hydrogenation. Challenging enantiomerically-enriched chiral anilide scaffolds were thereby obtained with high levels of enantio-control in the absence of toxic and cost-intensive silver salts. The resource-economy of the transformation was even improved by directly employing renewable solar energy.
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spelling pubmed-88901072022-03-24 Atropoenantioselective palladaelectro-catalyzed anilide C–H olefinations viable with natural sunlight as sustainable power source Frey, Johanna Hou, Xiaoyan Ackermann, Lutz Chem Sci Chemistry Enantioselective electrocatalyzed transformations represent a major challenge. We herein achieved atropoenantioselective pallada-electrocatalyzed C–H olefinations and C–H allylations with high efficacy and enantioselectivity under exceedingly mild reaction conditions. With (S)-5-oxoproline as the chiral ligand, activated and non-activated olefins were suitable substrates for the electro-C–H activations. Dual catalysis was devised in terms of electro-C–H olefination, along with catalytic hydrogenation. Challenging enantiomerically-enriched chiral anilide scaffolds were thereby obtained with high levels of enantio-control in the absence of toxic and cost-intensive silver salts. The resource-economy of the transformation was even improved by directly employing renewable solar energy. The Royal Society of Chemistry 2022-02-10 /pmc/articles/PMC8890107/ /pubmed/35340853 http://dx.doi.org/10.1039/d1sc06135f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Frey, Johanna
Hou, Xiaoyan
Ackermann, Lutz
Atropoenantioselective palladaelectro-catalyzed anilide C–H olefinations viable with natural sunlight as sustainable power source
title Atropoenantioselective palladaelectro-catalyzed anilide C–H olefinations viable with natural sunlight as sustainable power source
title_full Atropoenantioselective palladaelectro-catalyzed anilide C–H olefinations viable with natural sunlight as sustainable power source
title_fullStr Atropoenantioselective palladaelectro-catalyzed anilide C–H olefinations viable with natural sunlight as sustainable power source
title_full_unstemmed Atropoenantioselective palladaelectro-catalyzed anilide C–H olefinations viable with natural sunlight as sustainable power source
title_short Atropoenantioselective palladaelectro-catalyzed anilide C–H olefinations viable with natural sunlight as sustainable power source
title_sort atropoenantioselective palladaelectro-catalyzed anilide c–h olefinations viable with natural sunlight as sustainable power source
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8890107/
https://www.ncbi.nlm.nih.gov/pubmed/35340853
http://dx.doi.org/10.1039/d1sc06135f
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