Copper(II)-Catalyzed Three-Component Arylation/Hydroamination Cascade from Allyl Alcohol: Access to 1-Aryl-2-sulfonylamino-propanes

[Image: see text] A new straightforward approach to 1-aryl-2-aminopropanes using easily accessible substrates has been developed. Simple allyl alcohol is shown to be an ideal synthetic equivalent of the C3 propane-1,2-diylium bis-cation synthon in three-component cascade reactions with arenes and su...

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Autores principales: Loro, Camilla, Papis, Marta, Foschi, Francesca, Broggini, Gianluigi, Poli, Giovanni, Oble, Julie
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10563128/
https://www.ncbi.nlm.nih.gov/pubmed/37747795
http://dx.doi.org/10.1021/acs.joc.3c01536
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author Loro, Camilla
Papis, Marta
Foschi, Francesca
Broggini, Gianluigi
Poli, Giovanni
Oble, Julie
author_facet Loro, Camilla
Papis, Marta
Foschi, Francesca
Broggini, Gianluigi
Poli, Giovanni
Oble, Julie
author_sort Loro, Camilla
collection PubMed
description [Image: see text] A new straightforward approach to 1-aryl-2-aminopropanes using easily accessible substrates has been developed. Simple allyl alcohol is shown to be an ideal synthetic equivalent of the C3 propane-1,2-diylium bis-cation synthon in three-component cascade reactions with arenes and sulfonamide nucleophiles to regioselectively afford 1-aryl-2-aminopropanes. The reaction is catalyzed by Cu(OTf)(2) and is expected to involve a Friedel–Crafts-type allylation of the arene, followed by hydroamination.
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spelling pubmed-105631282023-10-11 Copper(II)-Catalyzed Three-Component Arylation/Hydroamination Cascade from Allyl Alcohol: Access to 1-Aryl-2-sulfonylamino-propanes Loro, Camilla Papis, Marta Foschi, Francesca Broggini, Gianluigi Poli, Giovanni Oble, Julie J Org Chem [Image: see text] A new straightforward approach to 1-aryl-2-aminopropanes using easily accessible substrates has been developed. Simple allyl alcohol is shown to be an ideal synthetic equivalent of the C3 propane-1,2-diylium bis-cation synthon in three-component cascade reactions with arenes and sulfonamide nucleophiles to regioselectively afford 1-aryl-2-aminopropanes. The reaction is catalyzed by Cu(OTf)(2) and is expected to involve a Friedel–Crafts-type allylation of the arene, followed by hydroamination. American Chemical Society 2023-09-25 /pmc/articles/PMC10563128/ /pubmed/37747795 http://dx.doi.org/10.1021/acs.joc.3c01536 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Loro, Camilla
Papis, Marta
Foschi, Francesca
Broggini, Gianluigi
Poli, Giovanni
Oble, Julie
Copper(II)-Catalyzed Three-Component Arylation/Hydroamination Cascade from Allyl Alcohol: Access to 1-Aryl-2-sulfonylamino-propanes
title Copper(II)-Catalyzed Three-Component Arylation/Hydroamination Cascade from Allyl Alcohol: Access to 1-Aryl-2-sulfonylamino-propanes
title_full Copper(II)-Catalyzed Three-Component Arylation/Hydroamination Cascade from Allyl Alcohol: Access to 1-Aryl-2-sulfonylamino-propanes
title_fullStr Copper(II)-Catalyzed Three-Component Arylation/Hydroamination Cascade from Allyl Alcohol: Access to 1-Aryl-2-sulfonylamino-propanes
title_full_unstemmed Copper(II)-Catalyzed Three-Component Arylation/Hydroamination Cascade from Allyl Alcohol: Access to 1-Aryl-2-sulfonylamino-propanes
title_short Copper(II)-Catalyzed Three-Component Arylation/Hydroamination Cascade from Allyl Alcohol: Access to 1-Aryl-2-sulfonylamino-propanes
title_sort copper(ii)-catalyzed three-component arylation/hydroamination cascade from allyl alcohol: access to 1-aryl-2-sulfonylamino-propanes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10563128/
https://www.ncbi.nlm.nih.gov/pubmed/37747795
http://dx.doi.org/10.1021/acs.joc.3c01536
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