762-70-9Relevant articles and documents
Molecular design principles of ionic liquids with a sulfonyl fluoride moiety
Siegel, David J.,Anderson, Grace I.,Cyr, Noah,Lambrecht, Daniel S.,Zeller, Matthias,Hillesheim, Patrick C.,Mirjafari, Arsalan
, p. 2443 - 2452 (2021)
The continued success of ionic liquids in applications ranging from energy to medicine poses the challenge to rapidly find new functional ionic liquids with desirable properties while developing practical, scalable syntheses. As a SuFExable functionality, the sulfonyl fluoride has become widely adopted throughout the field of chemical biology due, in part, to its unique stability-reactivity pattern, highlighting the underappreciated potential of the SVI-F motif in materials chemistry. For the first time, we herein report the development of a set of sulfonyl fluoride-functionalized ionic liquids with considerable structural diversityviaan efficient, modular, and orthogonal fluorosulfonylethylation procedure. The resulting SO2F-functionalized ionic milieu has properties consistent with its classification as ionic liquids. We employed a combination of molecular design, synthesis, computational modeling, and X-ray crystallographic studies to gain in-depth understanding of their structure-property correlations. The diversification of the SO2F-bearing salts is extended to include active pharmaceutical precursors, allowing for access to functional materials witha priorilow toxicity.
Metal-Free Synthesis of Functional 1-Substituted-1,2,3-Triazoles from Ethenesulfonyl Fluoride and Organic Azides
Giel, Marie-Claire,Smedley, Christopher J.,Mackie, Emily R. R.,Guo, Taijie,Dong, Jiajia,Soares da Costa, Tatiana P.,Moses, John E.
supporting information, p. 1181 - 1186 (2019/12/11)
The boom in growth of 1,4-disubstituted triazole products, in particular, since the early 2000’s, can be largely attributed to the birth of click chemistry and the discovery of the CuI-catalyzed azide–alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1-substituted-1,2,3-triazoles has been surprisingly more challenging. Reported here is a straightforward and scalable click-inspired protocol for the synthesis of 1-substituted-1,2,3-triazoles from organic azides and the bench stable acetylene surrogate ethenesulfonyl fluoride (ESF). The new transformation tolerates a wide selection of substrates and proceeds smoothly under metal-free conditions to give the products in excellent yield. Under controlled acidic conditions, the 1-substituted-1,2,3-triazole products undergo a Michael addition reaction with a second equivalent of ESF to give the unprecedented 1-substituted triazolium sulfonyl fluoride salts.
Ethenesulfonyl Fluoride (ESF): An On-Water Procedure for the Kilogram-Scale Preparation
Zheng, Qinheng,Dong, Jiajia,Sharpless, K. Barry
, p. 11360 - 11362 (2016/11/29)
A two-step, on-water procedure for the synthesis of ethenesulfonyl fluoride (ESF) is described. 2-Chloroethanesulfonyl fluoride is made via a neat reaction with an aqueous, nearly saturated potassium bifluoride solution from readily available 2-chloroetha
