Silicon‐Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism

SuFEx reactions, in which an S−F moiety reacts with a silyl‐protected phenol, have been developed as powerful click reactions. In the current paper we open up the potential of SuFEx reactions as enantioselective reactions, analyze the role of Si and outline the mechanism of this reaction. As a resul...

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Detalles Bibliográficos
Autores principales: Liang, Dong‐Dong, Streefkerk, Dieuwertje E., Jordaan, Daan, Wagemakers, Jorden, Baggerman, Jacob, Zuilhof, Han
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7216998/
https://www.ncbi.nlm.nih.gov/pubmed/32157791
http://dx.doi.org/10.1002/anie.201915519
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author Liang, Dong‐Dong
Streefkerk, Dieuwertje E.
Jordaan, Daan
Wagemakers, Jorden
Baggerman, Jacob
Zuilhof, Han
author_facet Liang, Dong‐Dong
Streefkerk, Dieuwertje E.
Jordaan, Daan
Wagemakers, Jorden
Baggerman, Jacob
Zuilhof, Han
author_sort Liang, Dong‐Dong
collection PubMed
description SuFEx reactions, in which an S−F moiety reacts with a silyl‐protected phenol, have been developed as powerful click reactions. In the current paper we open up the potential of SuFEx reactions as enantioselective reactions, analyze the role of Si and outline the mechanism of this reaction. As a result, fast, high‐yielding, “Si‐free” and enantiospecific SuFEx reactions of sulfonimidoyl fluorides have been developed, and their mechanism shown, by both experimental and theoretical methods, to yield chiral products.
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spelling pubmed-72169982020-05-13 Silicon‐Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism Liang, Dong‐Dong Streefkerk, Dieuwertje E. Jordaan, Daan Wagemakers, Jorden Baggerman, Jacob Zuilhof, Han Angew Chem Int Ed Engl Research Articles SuFEx reactions, in which an S−F moiety reacts with a silyl‐protected phenol, have been developed as powerful click reactions. In the current paper we open up the potential of SuFEx reactions as enantioselective reactions, analyze the role of Si and outline the mechanism of this reaction. As a result, fast, high‐yielding, “Si‐free” and enantiospecific SuFEx reactions of sulfonimidoyl fluorides have been developed, and their mechanism shown, by both experimental and theoretical methods, to yield chiral products. John Wiley and Sons Inc. 2020-03-11 2020-05-04 /pmc/articles/PMC7216998/ /pubmed/32157791 http://dx.doi.org/10.1002/anie.201915519 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Research Articles
Liang, Dong‐Dong
Streefkerk, Dieuwertje E.
Jordaan, Daan
Wagemakers, Jorden
Baggerman, Jacob
Zuilhof, Han
Silicon‐Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism
title Silicon‐Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism
title_full Silicon‐Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism
title_fullStr Silicon‐Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism
title_full_unstemmed Silicon‐Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism
title_short Silicon‐Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism
title_sort silicon‐free sufex reactions of sulfonimidoyl fluorides: scope, enantioselectivity, and mechanism
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7216998/
https://www.ncbi.nlm.nih.gov/pubmed/32157791
http://dx.doi.org/10.1002/anie.201915519
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