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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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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. |
format | Online Article Text |
id | pubmed-10108028 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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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