Literature DB >> 29327935

Introduction of a Crystalline, Shelf-Stable Reagent for the Synthesis of Sulfur(VI) Fluorides.

Hua Zhou1, Paramita Mukherjee2, Rongqiang Liu1, Edelweiss Evrard3, Dianpeng Wang1, John M Humphrey2, Todd W Butler2, Lise R Hoth2, Jeffrey B Sperry2, Sylvie K Sakata4, Christopher J Helal2, Christopher W Am Ende2.   

Abstract

The design, synthesis, and application of [4-(acetylamino)phenyl]imidodisulfuryl difluoride (AISF), a shelf-stable, crystalline reagent for the synthesis of sulfur(VI) fluorides, is described. The utility of AISF is demonstrated in the synthesis of a diverse array of aryl fluorosulfates and sulfamoyl fluorides under mild conditions. Additionally, a single-step preparation of AISF was developed that installed the bis(fluorosulfonyl)imide group on acetanilide utilizing an oxidative C-H functionalization protocol.

Entities:  

Year:  2018        PMID: 29327935     DOI: 10.1021/acs.orglett.7b03950

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  17 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.  Bioorthogonal chemistry.

Authors:  Samuel L Scinto; Didier A Bilodeau; Robert Hincapie; Wankyu Lee; Sean S Nguyen; Minghao Xu; Christopher W Am Ende; M G Finn; Kathrin Lang; Qing Lin; John Paul Pezacki; Jennifer A Prescher; Marc S Robillard; Joseph M Fox
Journal:  Nat Rev Methods Primers       Date:  2021-04-15

3.  Covalent labeling of a chromatin reader domain using proximity-reactive cyclic peptides.

Authors:  Meng Yao Zhang; Hyunjun Yang; Gloria Ortiz; Michael J Trnka; Nektaria Petronikolou; Alma L Burlingame; William F DeGrado; Danica Galonić Fujimori
Journal:  Chem Sci       Date:  2022-05-12       Impact factor: 9.969

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.  Emerging Utility of Fluorosulfate Chemical Probes.

Authors:  Lyn H Jones
Journal:  ACS Med Chem Lett       Date:  2018-06-27       Impact factor: 4.345

6.  Sulfur [18F]Fluoride Exchange Click Chemistry Enabled Ultrafast Late-Stage Radiosynthesis.

Authors:  Qinheng Zheng; Hongtao Xu; Hua Wang; Wen-Ge Han Du; Nan Wang; Huan Xiong; Yuang Gu; Louis Noodleman; K Barry Sharpless; Guang Yang; Peng Wu
Journal:  J Am Chem Soc       Date:  2021-02-25       Impact factor: 15.419

Review 7.  Arylfluorosulfate-Based Electrophiles for Covalent Protein Labeling: A New Addition to the Arsenal.

Authors:  Pablo Martín-Gago; Christian A Olsen
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-26       Impact factor: 15.336

8.  Site-Selective, Modular Diversification of Polyhalogenated Aryl Fluorosulfates (ArOSO2 F) Enabled by an Air-Stable PdI Dimer.

Authors:  Marvin Mendel; Indrek Kalvet; Daniel Hupperich; Guillaume Magnin; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-16       Impact factor: 15.336

9.  Synthesis of unsymmetrical sulfamides and polysulfamides via SuFEx click chemistry.

Authors:  Ryan W Kulow; Jiun Wei Wu; Cheoljae Kim; Quentin Michaudel
Journal:  Chem Sci       Date:  2020-07-13       Impact factor: 9.825

10.  Silicon-Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism.

Authors:  Dong-Dong Liang; Dieuwertje E Streefkerk; Daan Jordaan; Jorden Wagemakers; Jacob Baggerman; Han Zuilhof
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-11       Impact factor: 15.336

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