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CC BY-NC-ND 4.0 · Synthesis
DOI: 10.1055/a-2410-2039
DOI: 10.1055/a-2410-2039
short review
SuFEx Chemistry
A Practical Guide to SuFEx Chemistry: An Overview of S(VI)-SuFEx Linkers and Their Reactivity
We thank the Universita degli Studi di Bari Aldo Moro and the Consorzio Interuniversitario Nazionale sulle Metodologie e Processi Innovativi di Sintesi (CINMPIS consortium). D.S. and R.L. acknowledge funding from the European Commission's Horizon Europe research and innovation programme through the Marie Skłodowska-Curie doctoral network "GreenDigiPharma" (grant agreement No 101073089). P.N. acknowledges funding from the European Commission's Horizon Europe research and innovation programme through a Marie Skłodowska-Curie Postdoctoral Fellowship "ExpandFlow" (grant agreement No. 101106497).
Abstract
Sulfur(VI)–fluoride exchange (SuFEx) is a second generation, metal-free click chemistry concept introduced by Sharpless in 2014. Since the introduction of the concept, a large variety of synthetic methodologies to S(VI)-SuFEx hubs, and their derivatization with oxygen-, nitrogen-, and carbon-based nucleophiles have been developed. Herein, we provide a concise and practical overview for their preparation, SuFExability, inclusive of which substituents are tolerated. The stereoselective synthesis of aza-derivatives is also discussed.
1 Introduction
2 Synthesis of SuFEx Hubs
2.1 Sulfonyl Fluorides
2.2 Fluorosulfates
2.3 Sulfamoyl Fluorides
2.4 Sulfonimidoyl Fluorides
2.5 Sulfuramidimidoyl Fluorides and Sulfurofluoridoimidates
2.6 Sulfondiimidoyl Fluorides
3 Reactivity of SuFEx Hubs
3.1 Reactivity of Sulfonyl Fluorides
3.2 Reactivity of Fluorosulfates
3.3 Reactivity of Sulfamoyl Fluorides
3.4 Reactivity of Sulfonimidoyl Fluorides
3.5 Reactivity of Sulfurofluoridoimidates
3.6 Reactivity of Sulfondiimidoyl Fluorides
4 Stereochemical Considerations in SuFEx Chemistry
5 Conclusion and Outlook
Publication History
Received: 01 August 2024
Accepted: 05 September 2024
Accepted Manuscript online:
05 September 2024
Article published online:
28 October 2024
© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
Georg Thieme Verlag KG
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