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Sulfur-Phenolate Exchange as a Mild, Fast, and High-Yielding Method toward the Synthesis of Sulfonamides

[Image: see text] Sulfonamides have many important biological applications, yet their synthesis often involves long reaction times under dry and non-ambient conditions. Here we report the synthesis of a large range of sulfonamides at room temperature using 4-nitrophenyl benzylsulfonate as a starting...

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Autores principales: van den Boom, Alyssa F. J., Zuilhof, Han
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9926510/
https://www.ncbi.nlm.nih.gov/pubmed/36720015
http://dx.doi.org/10.1021/acs.orglett.2c04292
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author van den Boom, Alyssa F. J.
Zuilhof, Han
author_facet van den Boom, Alyssa F. J.
Zuilhof, Han
author_sort van den Boom, Alyssa F. J.
collection PubMed
description [Image: see text] Sulfonamides have many important biological applications, yet their synthesis often involves long reaction times under dry and non-ambient conditions. Here we report the synthesis of a large range of sulfonamides at room temperature using 4-nitrophenyl benzylsulfonate as a starting material. Sulfonamides were prepared from a wide range of aliphatic, linear, and cyclic amines, anilines, and N-methylanilines. The yields and reaction times observed here were comparable to or better than those reported previously, establishing sulfur-phenolate exchange as a viable alternative.
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spelling pubmed-99265102023-02-15 Sulfur-Phenolate Exchange as a Mild, Fast, and High-Yielding Method toward the Synthesis of Sulfonamides van den Boom, Alyssa F. J. Zuilhof, Han Org Lett [Image: see text] Sulfonamides have many important biological applications, yet their synthesis often involves long reaction times under dry and non-ambient conditions. Here we report the synthesis of a large range of sulfonamides at room temperature using 4-nitrophenyl benzylsulfonate as a starting material. Sulfonamides were prepared from a wide range of aliphatic, linear, and cyclic amines, anilines, and N-methylanilines. The yields and reaction times observed here were comparable to or better than those reported previously, establishing sulfur-phenolate exchange as a viable alternative. American Chemical Society 2023-01-31 /pmc/articles/PMC9926510/ /pubmed/36720015 http://dx.doi.org/10.1021/acs.orglett.2c04292 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 van den Boom, Alyssa F. J.
Zuilhof, Han
Sulfur-Phenolate Exchange as a Mild, Fast, and High-Yielding Method toward the Synthesis of Sulfonamides
title Sulfur-Phenolate Exchange as a Mild, Fast, and High-Yielding Method toward the Synthesis of Sulfonamides
title_full Sulfur-Phenolate Exchange as a Mild, Fast, and High-Yielding Method toward the Synthesis of Sulfonamides
title_fullStr Sulfur-Phenolate Exchange as a Mild, Fast, and High-Yielding Method toward the Synthesis of Sulfonamides
title_full_unstemmed Sulfur-Phenolate Exchange as a Mild, Fast, and High-Yielding Method toward the Synthesis of Sulfonamides
title_short Sulfur-Phenolate Exchange as a Mild, Fast, and High-Yielding Method toward the Synthesis of Sulfonamides
title_sort sulfur-phenolate exchange as a mild, fast, and high-yielding method toward the synthesis of sulfonamides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9926510/
https://www.ncbi.nlm.nih.gov/pubmed/36720015
http://dx.doi.org/10.1021/acs.orglett.2c04292
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