Sulfur-Phenolate Exchange As a Fluorine-Free Approach to S(VI) Exchange Chemistry on Sulfonyl Moieties

[Image: see text] SuFEx chemistry has recently evolved as next-generation click chemistry. However, in most SuFEx syntheses, additional reagents/catalysts and carefully controlled conditions are still needed. Here, we aim to further generalize S(VI) exchange chemistry, using 4-nitrophenyl phenylmeth...

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Autores principales: van den Boom, Alyssa F.J., Subramaniam, Muthusamy, Zuilhof, Han
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9724081/
https://www.ncbi.nlm.nih.gov/pubmed/36383144
http://dx.doi.org/10.1021/acs.orglett.2c03421
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author van den Boom, Alyssa F.J.
Subramaniam, Muthusamy
Zuilhof, Han
author_facet van den Boom, Alyssa F.J.
Subramaniam, Muthusamy
Zuilhof, Han
author_sort van den Boom, Alyssa F.J.
collection PubMed
description [Image: see text] SuFEx chemistry has recently evolved as next-generation click chemistry. However, in most SuFEx syntheses, additional reagents/catalysts and carefully controlled conditions are still needed. Here, we aim to further generalize S(VI) exchange chemistry, using 4-nitrophenyl phenylmethanesulfonate as example, in which the nitrophenolate group is exchanged for a wide range of (substituted) phenols and alkyl alcohols. Quantitative yields were reached within 10 min under ambient conditions and required only filtering through silica as workup.
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spelling pubmed-97240812022-12-07 Sulfur-Phenolate Exchange As a Fluorine-Free Approach to S(VI) Exchange Chemistry on Sulfonyl Moieties van den Boom, Alyssa F.J. Subramaniam, Muthusamy Zuilhof, Han Org Lett [Image: see text] SuFEx chemistry has recently evolved as next-generation click chemistry. However, in most SuFEx syntheses, additional reagents/catalysts and carefully controlled conditions are still needed. Here, we aim to further generalize S(VI) exchange chemistry, using 4-nitrophenyl phenylmethanesulfonate as example, in which the nitrophenolate group is exchanged for a wide range of (substituted) phenols and alkyl alcohols. Quantitative yields were reached within 10 min under ambient conditions and required only filtering through silica as workup. American Chemical Society 2022-11-16 2022-12-02 /pmc/articles/PMC9724081/ /pubmed/36383144 http://dx.doi.org/10.1021/acs.orglett.2c03421 Text en © 2022 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.
Subramaniam, Muthusamy
Zuilhof, Han
Sulfur-Phenolate Exchange As a Fluorine-Free Approach to S(VI) Exchange Chemistry on Sulfonyl Moieties
title Sulfur-Phenolate Exchange As a Fluorine-Free Approach to S(VI) Exchange Chemistry on Sulfonyl Moieties
title_full Sulfur-Phenolate Exchange As a Fluorine-Free Approach to S(VI) Exchange Chemistry on Sulfonyl Moieties
title_fullStr Sulfur-Phenolate Exchange As a Fluorine-Free Approach to S(VI) Exchange Chemistry on Sulfonyl Moieties
title_full_unstemmed Sulfur-Phenolate Exchange As a Fluorine-Free Approach to S(VI) Exchange Chemistry on Sulfonyl Moieties
title_short Sulfur-Phenolate Exchange As a Fluorine-Free Approach to S(VI) Exchange Chemistry on Sulfonyl Moieties
title_sort sulfur-phenolate exchange as a fluorine-free approach to s(vi) exchange chemistry on sulfonyl moieties
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9724081/
https://www.ncbi.nlm.nih.gov/pubmed/36383144
http://dx.doi.org/10.1021/acs.orglett.2c03421
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AT zuilhofhan sulfurphenolateexchangeasafluorinefreeapproachtosviexchangechemistryonsulfonylmoieties

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