Literature DB >> 29796551

1-Bromoethene-1-sulfonyl fluoride (BESF) is another good connective hub for SuFEx click chemistry.

Christopher J Smedley1, Marie-Claire Giel1, Andrew Molino1, Andrew S Barrow1, David J D Wilson1, John E Moses1.   

Abstract

We demonstrate 1,2-dibromoethane-1-sulfonyl fluoride (DESF) as a bench-stable and readily accessible precursor to the robust SuFEx connector, 1-bromoethene-1-sulfonyl fluoride (BESF). The in situ generation of BESF from DESF opens up several new reaction profiles, including application in the syntheses of unprecedented 3-substituted isoxazole-5-sulfonyl fluorides, 1-substituted-1H-1,2,3-triazole-4-sulfonyl fluorides, 2-amino-1-bromoethane-1-sulfonyl fluorides and 4-bromo-β-sultams in good to excellent yields. These new modules comprise a pendant sulfonyl fluoride handle, which further undergoes facile and selective SuFEx reactions with a selection of aryl silyl ethers to generate stable and useful sulfonate connections.

Entities:  

Year:  2018        PMID: 29796551     DOI: 10.1039/c8cc03400a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  10 in total

1.  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

2.  Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs.

Authors:  Christopher J Smedley; Gencheng Li; Andrew S Barrow; Timothy L Gialelis; Marie-Claire Giel; Alessandra Ottonello; Yunfei Cheng; Seiya Kitamura; Dennis W Wolan; K Barry Sharpless; John E Moses
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-04       Impact factor: 15.336

3.  Accelerated SuFEx Click Chemistry For Modular Synthesis.

Authors:  Christopher J Smedley; Joshua A Homer; Timothy L Gialelis; Andrew S Barrow; Rebecca A Koelln; John E Moses
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-07       Impact factor: 15.336

4.  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

5.  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

6.  SuFExable NH-Pyrazoles via 1,3-Dipolar Cycloadditions of Diazo Compounds with Bromoethenylsulfonyl Fluoride.

Authors:  Pavel Yamanushkin; Kemal Kaya; Mark Aldren M Feliciano; Brian Gold
Journal:  J Org Chem       Date:  2022-02-10       Impact factor: 4.198

7.  Rh-Catalyzed Highly Enantioselective Synthesis of Aliphatic Sulfonyl Fluorides.

Authors:  Balakrishna Moku; Wan-Yin Fang; Jing Leng; Linxian Li; Gao-Feng Zha; K P Rakesh; Hua-Li Qin
Journal:  iScience       Date:  2019-10-30

8.  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

Review 9.  Triazoles and Their Derivatives: Chemistry, Synthesis, and Therapeutic Applications.

Authors:  Mohammed M Matin; Priyanka Matin; Md Rezaur Rahman; Taibi Ben Hadda; Faisal A Almalki; Shafi Mahmud; Mohammed M Ghoneim; Maha Alruwaily; Sultan Alshehri
Journal:  Front Mol Biosci       Date:  2022-04-25

10.  Introducing SuFNucs: Sulfamoyl-Fluoride-Functionalized Nucleosides That Undergo Sulfur Fluoride Exchange Reaction.

Authors:  Mikołaj Chrominski; Kamil Ziemkiewicz; Joanna Kowalska; Jacek Jemielity
Journal:  Org Lett       Date:  2022-06-30       Impact factor: 6.072

  10 in total

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