Electrophilic Reagents for the Direct Incorporation of Uncommon SCF(2)CF(2)H and SCF(2)CF(3) Motifs

[Image: see text] The introduction of fluoroalkylthioether groups has attracted the attention of the drug-discovery community given the special physicochemical and pharmacokinetic features they confer to bioactive compounds, yet these are often limited to standard SCF(3) and SCF(2)H moieties. Herein...

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Autores principales: Mestre, Jordi, Bernús, Miguel, Castillón, Sergio, Boutureira, Omar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9400389/
https://www.ncbi.nlm.nih.gov/pubmed/35944166
http://dx.doi.org/10.1021/acs.joc.2c01038
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author Mestre, Jordi
Bernús, Miguel
Castillón, Sergio
Boutureira, Omar
author_facet Mestre, Jordi
Bernús, Miguel
Castillón, Sergio
Boutureira, Omar
author_sort Mestre, Jordi
collection PubMed
description [Image: see text] The introduction of fluoroalkylthioether groups has attracted the attention of the drug-discovery community given the special physicochemical and pharmacokinetic features they confer to bioactive compounds, yet these are often limited to standard SCF(3) and SCF(2)H moieties. Herein, two saccharin-based electrophilic reagents have been disclosed for the incorporation of uncommon SCF(2)CF(2)H and SCF(2)CF(3) motifs. Their reactivity performance, multigram-scale preparation, and divergent derivatization have been thoroughly investigated with a variety of nucleophiles, including natural products and pharmaceuticals.
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spelling pubmed-94003892022-08-25 Electrophilic Reagents for the Direct Incorporation of Uncommon SCF(2)CF(2)H and SCF(2)CF(3) Motifs Mestre, Jordi Bernús, Miguel Castillón, Sergio Boutureira, Omar J Org Chem [Image: see text] The introduction of fluoroalkylthioether groups has attracted the attention of the drug-discovery community given the special physicochemical and pharmacokinetic features they confer to bioactive compounds, yet these are often limited to standard SCF(3) and SCF(2)H moieties. Herein, two saccharin-based electrophilic reagents have been disclosed for the incorporation of uncommon SCF(2)CF(2)H and SCF(2)CF(3) motifs. Their reactivity performance, multigram-scale preparation, and divergent derivatization have been thoroughly investigated with a variety of nucleophiles, including natural products and pharmaceuticals. American Chemical Society 2022-08-09 2022-08-19 /pmc/articles/PMC9400389/ /pubmed/35944166 http://dx.doi.org/10.1021/acs.joc.2c01038 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 Mestre, Jordi
Bernús, Miguel
Castillón, Sergio
Boutureira, Omar
Electrophilic Reagents for the Direct Incorporation of Uncommon SCF(2)CF(2)H and SCF(2)CF(3) Motifs
title Electrophilic Reagents for the Direct Incorporation of Uncommon SCF(2)CF(2)H and SCF(2)CF(3) Motifs
title_full Electrophilic Reagents for the Direct Incorporation of Uncommon SCF(2)CF(2)H and SCF(2)CF(3) Motifs
title_fullStr Electrophilic Reagents for the Direct Incorporation of Uncommon SCF(2)CF(2)H and SCF(2)CF(3) Motifs
title_full_unstemmed Electrophilic Reagents for the Direct Incorporation of Uncommon SCF(2)CF(2)H and SCF(2)CF(3) Motifs
title_short Electrophilic Reagents for the Direct Incorporation of Uncommon SCF(2)CF(2)H and SCF(2)CF(3) Motifs
title_sort electrophilic reagents for the direct incorporation of uncommon scf(2)cf(2)h and scf(2)cf(3) motifs
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9400389/
https://www.ncbi.nlm.nih.gov/pubmed/35944166
http://dx.doi.org/10.1021/acs.joc.2c01038
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