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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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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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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. |
format | Online Article Text |
id | pubmed-9926510 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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