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The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection

C−H bond formylation is the most immediate way to incorporate the versatile formyl group into (hetero)aromatics. However, the type of reagents and severe conditions involved in the classical formylation methods often curtail their application, especially in the presence of other functional groups. H...

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Autores principales: Antón‐Cánovas, Teresa, Alonso, Francisco
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10108028/
https://www.ncbi.nlm.nih.gov/pubmed/36448641
http://dx.doi.org/10.1002/anie.202215916
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author Antón‐Cánovas, Teresa
Alonso, Francisco
author_facet Antón‐Cánovas, Teresa
Alonso, Francisco
author_sort Antón‐Cánovas, Teresa
collection PubMed
description C−H bond formylation is the most immediate way to incorporate the versatile formyl group into (hetero)aromatics. However, the type of reagents and severe conditions involved in the classical formylation methods often curtail their application, especially in the presence of other functional groups. Herein, we present the Eschenmoser's salt, a commercially available (dimethylamino)methylating chemical, as a useful reagent for the C−H formylation of indolizines and other compounds. The method is straightforward and mild, furnishing indolizinecarbaldehydes in modest‐to‐good yields with exclusive and remote regioselectivity. Furthermore, these compounds can be easily transformed into push‐pull dyes and are highly selective in the colorimetric detection of nitrite, a substance extensively employed as preservative in the food industry, the concentration of which is crucial to control to prevent harmful effects in living organisms. The assay is simple, allowing the naked‐eye detection of nitrite in solution or on a cotton swab for a wide range of concentrations.
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spelling pubmed-101080282023-04-18 The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection Antón‐Cánovas, Teresa Alonso, Francisco Angew Chem Int Ed Engl Research Articles C−H bond formylation is the most immediate way to incorporate the versatile formyl group into (hetero)aromatics. However, the type of reagents and severe conditions involved in the classical formylation methods often curtail their application, especially in the presence of other functional groups. Herein, we present the Eschenmoser's salt, a commercially available (dimethylamino)methylating chemical, as a useful reagent for the C−H formylation of indolizines and other compounds. The method is straightforward and mild, furnishing indolizinecarbaldehydes in modest‐to‐good yields with exclusive and remote regioselectivity. Furthermore, these compounds can be easily transformed into push‐pull dyes and are highly selective in the colorimetric detection of nitrite, a substance extensively employed as preservative in the food industry, the concentration of which is crucial to control to prevent harmful effects in living organisms. The assay is simple, allowing the naked‐eye detection of nitrite in solution or on a cotton swab for a wide range of concentrations. John Wiley and Sons Inc. 2022-12-20 2023-01-23 /pmc/articles/PMC10108028/ /pubmed/36448641 http://dx.doi.org/10.1002/anie.202215916 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Research Articles
Antón‐Cánovas, Teresa
Alonso, Francisco
The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection
title The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection
title_full The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection
title_fullStr The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection
title_full_unstemmed The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection
title_short The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection
title_sort eschenmoser's salt as a formylation agent for the synthesis of indolizinecarbaldehydes and their use for colorimetric nitrite detection
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10108028/
https://www.ncbi.nlm.nih.gov/pubmed/36448641
http://dx.doi.org/10.1002/anie.202215916
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