Literature DB >> 27159425

Ethenesulfonyl Fluoride: The Most Perfect Michael Acceptor Ever Found?

Quan Chen1, Peter Mayer1, Herbert Mayr2.   

Abstract

The kinetics of the reactions of ethenesulfonyl fluoride (ESF) with sulfonium and pyridinium ylides were measured photometrically to determine the electrophilicity parameter of ESF according to the correlation lg k20 °C =sN (N+E). With E=-12.09, ESF is among the strongest Michael acceptors in our comprehensive electrophilicity scale, which explains its excellent performance in reactions with many nucleophiles. Its predicted usability as a reagent in electrophilic aromatic substitutions with electron-rich arenes was confirmed by uncatalyzed reactions with alkyl-substituted pyrroles.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  electrophilic aromatic substitution; electrophilicity; linear free-energy relationships; reaction kinetics; ylides

Year:  2016        PMID： 27159425     DOI： 10.1002/anie.201601875

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  9 in total

1.  Utilizing Carbonyl Coordination of Native Amides for Palladium-Catalyzed C(sp3 )-H Olefination.

Authors:  Hojoon Park; Yang Li; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-04       Impact factor: 15.336

2.  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

3.  A Heck-Matsuda Process for the Synthesis of β-Arylethenesulfonyl Fluorides: Selectively Addressable Bis-electrophiles for SuFEx Click Chemistry.

Authors:  Hua-Li Qin; Qinheng Zheng; Grant A L Bare; Peng Wu; K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

4.  A practical fluorosulfonylating platform via photocatalytic imidazolium-based SO2F radical reagent.

Authors:  Weigang Zhang; Heyin Li; Xiaojuan Li; Zhenlei Zou; Mengjun Huang; Jiyang Liu; Xiaochen Wang; Shengyang Ni; Yi Pan; Yi Wang
Journal:  Nat Commun       Date:  2022-06-18       Impact factor: 17.694

5.  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

Review 6.  Sulfur - fluorine bond in PET radiochemistry.

Authors:  Giancarlo Pascali; Lidia Matesic; Bo Zhang; Andrew T King; Andrea J Robinson; Alison T Ung; Benjamin H Fraser
Journal:  EJNMMI Radiopharm Chem       Date:  2017-07-17

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

9.  Olefination with Sulfonyl Halides and Esters: Synthesis of Unsaturated Sulfonyl Fluorides.

Authors:  Michał Tryniszewski; Dariusz Basiak; Michał Barbasiewicz
Journal:  Org Lett       Date:  2022-06-02       Impact factor: 6.072
  9 in total

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