Literature DB >> 27764941

Ethenesulfonyl Fluoride (ESF): An On-Water Procedure for the Kilogram-Scale Preparation.

Qinheng Zheng1, Jiajia Dong1, K Barry Sharpless1.   

Abstract

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-chloroethanesulfonyl chloride. The subsequent dehydrochlorination of 2-chloroethanesulfonyl fluoride proceeds neatly with magnesium oxide as the base in an aqueous suspension to give ESF. This recipe allows the preparation of ESF in 98% yield on a kilogram scale.

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Year:  2016        PMID： 27764941     DOI： 10.1021/acs.joc.6b01423

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  11 in total

1.  SuFEx Chemistry of Thionyl Tetrafluoride (SOF4 ) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates.

Authors:  Bing Gao; Suhua Li; Peng Wu; John E Moses; K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-16       Impact factor: 15.336

2.  SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase.

Authors:  Qinheng Zheng; Jordan L Woehl; Seiya Kitamura; Diogo Santos-Martins; Christopher J Smedley; Gencheng Li; Stefano Forli; John E Moses; Dennis W Wolan; K Barry Sharpless
Journal:  Proc Natl Acad Sci U S A       Date:  2019-09-04       Impact factor: 11.205

3.  Palladium-Catalyzed Fluorosulfonylvinylation of Organic Iodides.

Authors:  Gao-Feng Zha; Qinheng Zheng; Jing Leng; Peng Wu; Hua-Li Qin; K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2017-03-29       Impact factor: 15.336

4.  SuFEx-Based Polysulfonate Formation from Ethenesulfonyl Fluoride-Amine Adducts.

Authors:  Hua Wang; Feng Zhou; Gerui Ren; Qinheng Zheng; Hongli Chen; Bing Gao; Liana Klivansky; Yi Liu; Bin Wu; Qingfeng Xu; Jianmei Lu; K Barry Sharpless; Peng Wu
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-18       Impact factor: 15.336

5.  Biocompatible SuFEx Click Chemistry: Thionyl Tetrafluoride (SOF4 )-Derived Connective Hubs for Bioconjugation to DNA and Proteins.

Authors:  Feng Liu; Hua Wang; Suhua Li; Grant A L Bare; Xuemin Chen; Chu Wang; John E Moses; Peng Wu; K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-08       Impact factor: 15.336

6.  SuFExable polymers with helical structures derived from thionyl tetrafluoride.

Authors:  Suhua Li; Gencheng Li; Bing Gao; Sidharam P Pujari; Xiaoyan Chen; Hyunseok Kim; Feng Zhou; Liana M Klivansky; Yi Liu; Hafedh Driss; Dong-Dong Liang; Jianmei Lu; Peng Wu; Han Zuilhof; John Moses; K Barry Sharpless
Journal:  Nat Chem       Date:  2021-08-16       Impact factor: 24.274

7.  Diversity oriented clicking delivers β-substituted alkenyl sulfonyl fluorides as covalent human neutrophil elastase inhibitors.

Authors:  Yunfei Cheng; Gencheng Li; Christopher J Smedley; Marie-Claire Giel; Seiya Kitamura; Jordan L Woehl; Giulia Bianco; Stefano Forli; Joshua A Homer; John R Cappiello; Dennis W Wolan; John E Moses; K Barry Sharpless
Journal:  Proc Natl Acad Sci U S A       Date:  2022-09-07       Impact factor: 12.779

8.  Quantitative and Orthogonal Formation and Reactivity of SuFEx Platforms.

Authors:  Digvijay Gahtory; Rickdeb Sen; Sidharam Pujari; Suhua Li; Qinheng Zheng; John E Moses; K Barry Sharpless; Han Zuilhof
Journal:  Chemistry       Date:  2018-06-27       Impact factor: 5.236

9.  Cyclic Alkenylsulfonyl Fluorides: Palladium-Catalyzed Synthesis and Functionalization of Compact Multifunctional Reagents.

Authors:  Terry Shing-Bong Lou; Scott W Bagley; Michael C Willis
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-06       Impact factor: 15.336

10.  SuFEx-enabled, chemoselective synthesis of triflates, triflamides and triflimidates.

Authors:  Bing-Yu Li; Lauren Voets; Ruben Van Lommel; Fien Hoppenbrouwers; Mercedes Alonso; Steven H L Verhelst; Wim M De Borggraeve; Joachim Demaerel
Journal:  Chem Sci       Date:  2022-01-05       Impact factor: 9.825
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