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Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts

[Image: see text] The arylethylamine pharmacophore is conserved across a range of biologically active natural products and pharmaceuticals, particularly in molecules that act on the central nervous system. Herein, we present a photoinduced copper-catalyzed azidoarylation of alkenes at a late stage w...

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Autores principales: Cai, Yuan, Chatterjee, Sagnik, Ritter, Tobias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10311530/
https://www.ncbi.nlm.nih.gov/pubmed/37307146
http://dx.doi.org/10.1021/jacs.3c04016
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author Cai, Yuan
Chatterjee, Sagnik
Ritter, Tobias
author_facet Cai, Yuan
Chatterjee, Sagnik
Ritter, Tobias
author_sort Cai, Yuan
collection PubMed
description [Image: see text] The arylethylamine pharmacophore is conserved across a range of biologically active natural products and pharmaceuticals, particularly in molecules that act on the central nervous system. Herein, we present a photoinduced copper-catalyzed azidoarylation of alkenes at a late stage with arylthianthrenium salts, allowing access to highly functionalized acyclic (hetero)arylethylamine scaffolds that are otherwise difficult to access. A mechanistic study is consistent with a rac-BINAP-Cu(I)-azide (2) as the photoactive catalytic species. We show the utility of the new method by the expedient synthesis of racemic melphalan in four steps through C–H functionalization.
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spelling pubmed-103115302023-07-01 Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts Cai, Yuan Chatterjee, Sagnik Ritter, Tobias J Am Chem Soc [Image: see text] The arylethylamine pharmacophore is conserved across a range of biologically active natural products and pharmaceuticals, particularly in molecules that act on the central nervous system. Herein, we present a photoinduced copper-catalyzed azidoarylation of alkenes at a late stage with arylthianthrenium salts, allowing access to highly functionalized acyclic (hetero)arylethylamine scaffolds that are otherwise difficult to access. A mechanistic study is consistent with a rac-BINAP-Cu(I)-azide (2) as the photoactive catalytic species. We show the utility of the new method by the expedient synthesis of racemic melphalan in four steps through C–H functionalization. American Chemical Society 2023-06-12 /pmc/articles/PMC10311530/ /pubmed/37307146 http://dx.doi.org/10.1021/jacs.3c04016 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 Cai, Yuan
Chatterjee, Sagnik
Ritter, Tobias
Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts
title Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts
title_full Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts
title_fullStr Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts
title_full_unstemmed Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts
title_short Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts
title_sort photoinduced copper-catalyzed late-stage azidoarylation of alkenes via arylthianthrenium salts
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10311530/
https://www.ncbi.nlm.nih.gov/pubmed/37307146
http://dx.doi.org/10.1021/jacs.3c04016
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