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Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins

Intermolecular carboamination of olefins offers a powerful platform for the rapid construction of structurally complex amines from abundant feedstocks. However, these reactions often require transition-metal catalysis, and are mainly limited to 1,2-carboamination. Herein, we report a novel radical r...

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Autores principales: Tan, Guangying, Paulus, Fritz, Petti, Alessia, Wiethoff, Maxim-Aleksa, Lauer, Anna, Daniliuc, Constantin, Glorius, Frank
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9977457/
https://www.ncbi.nlm.nih.gov/pubmed/36873844
http://dx.doi.org/10.1039/d2sc06497a
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author Tan, Guangying
Paulus, Fritz
Petti, Alessia
Wiethoff, Maxim-Aleksa
Lauer, Anna
Daniliuc, Constantin
Glorius, Frank
author_facet Tan, Guangying
Paulus, Fritz
Petti, Alessia
Wiethoff, Maxim-Aleksa
Lauer, Anna
Daniliuc, Constantin
Glorius, Frank
author_sort Tan, Guangying
collection PubMed
description Intermolecular carboamination of olefins offers a powerful platform for the rapid construction of structurally complex amines from abundant feedstocks. However, these reactions often require transition-metal catalysis, and are mainly limited to 1,2-carboamination. Herein, we report a novel radical relay 1,4-carboimination across two distinct olefins with alkyl carboxylic acid-derived bifunctional oxime esters via energy transfer catalysis. The reaction is highly chemo- and regioselective, and multiple C–C and C–N bonds were formed in a single orchestrated operation. This mild and metal-free method features a remarkably broad substrate scope with excellent tolerance of sensitive functional groups, therefore providing easy access to structurally diverse 1,4-carboiminated products. Moreover, the obtained imines could be easily converted into valuable biologically relevant free γ-amino acids.
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spelling pubmed-99774572023-03-02 Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins Tan, Guangying Paulus, Fritz Petti, Alessia Wiethoff, Maxim-Aleksa Lauer, Anna Daniliuc, Constantin Glorius, Frank Chem Sci Chemistry Intermolecular carboamination of olefins offers a powerful platform for the rapid construction of structurally complex amines from abundant feedstocks. However, these reactions often require transition-metal catalysis, and are mainly limited to 1,2-carboamination. Herein, we report a novel radical relay 1,4-carboimination across two distinct olefins with alkyl carboxylic acid-derived bifunctional oxime esters via energy transfer catalysis. The reaction is highly chemo- and regioselective, and multiple C–C and C–N bonds were formed in a single orchestrated operation. This mild and metal-free method features a remarkably broad substrate scope with excellent tolerance of sensitive functional groups, therefore providing easy access to structurally diverse 1,4-carboiminated products. Moreover, the obtained imines could be easily converted into valuable biologically relevant free γ-amino acids. The Royal Society of Chemistry 2023-02-03 /pmc/articles/PMC9977457/ /pubmed/36873844 http://dx.doi.org/10.1039/d2sc06497a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Tan, Guangying
Paulus, Fritz
Petti, Alessia
Wiethoff, Maxim-Aleksa
Lauer, Anna
Daniliuc, Constantin
Glorius, Frank
Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins
title Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins
title_full Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins
title_fullStr Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins
title_full_unstemmed Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins
title_short Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins
title_sort metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9977457/
https://www.ncbi.nlm.nih.gov/pubmed/36873844
http://dx.doi.org/10.1039/d2sc06497a
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