Literature DB >> 25100330

SuFEx-based synthesis of polysulfates.

Jiajia Dong1, Luke Kwisnek2, James S Oakdale2, K Barry Sharpless1, Valery V Fokin2.   

Abstract

High-molecular-weight polysulfates are readily formed from aromatic bis(silyl ethers) and bis(fluorosulfates) in the presence of a base catalyst. The reaction is fast and proceeds well under neat conditions or in solvents, such as dimethyl formamide or N-methylpyrrolidone, to provide the desired polymers in nearly quantitative yield. These polymers are more resistant to chemical degradation than their polycarbonate analogues and exhibit excellent mechanical, optical, and oxygen-barrier properties.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  SuFEx reaction; click chemistry; polymerization

Mesh:

Substances:

Year:  2014        PMID: 25100330      PMCID: PMC4442796          DOI: 10.1002/anie.201403758

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


  3 in total

1.  Click Chemistry: Diverse Chemical Function from a Few Good Reactions.

Authors:  Hartmuth C. Kolb; M. G. Finn; K. Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2001-06-01       Impact factor: 15.336

2.  A new strategy for deprotonative functionalization of aromatics: transformations with excellent chemoselectivity and unique regioselectivities using t-Bu-P4 base.

Authors:  Tatsushi Imahori; Yoshinori Kondo
Journal:  J Am Chem Soc       Date:  2003-07-09       Impact factor: 15.419

3.  Phosphazene base-promoted functionalization of aryltrimethylsilanes.

Authors:  Koichi Suzawa; Masahiro Ueno; Andrew E H Wheatley; Yoshinori Kondo
Journal:  Chem Commun (Camb)       Date:  2006-12-14       Impact factor: 6.222

  3 in total
  39 in total

1.  Liganding Functional Tyrosine Sites on Proteins Using Sulfur-Triazole Exchange Chemistry.

Authors:  Jeffrey W Brulet; Adam L Borne; Kun Yuan; Adam H Libby; Ku-Lung Hsu
Journal:  J Am Chem Soc       Date:  2020-04-24       Impact factor: 15.419

2.  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

3.  Sulfur(VI) Fluoride Exchange (SuFEx)-Enabled High-Throughput Medicinal Chemistry.

Authors:  Seiya Kitamura; Qinheng Zheng; Jordan L Woehl; Angelo Solania; Emily Chen; Nicholas Dillon; Mitchell V Hull; Miyako Kotaniguchi; John R Cappiello; Shinichi Kitamura; Victor Nizet; K Barry Sharpless; Dennis W Wolan
Journal:  J Am Chem Soc       Date:  2020-06-10       Impact factor: 15.419

4.  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

5.  Synthesis of Sulfotyrosine-Containing Peptides by Incorporating Fluorosulfated Tyrosine Using an Fmoc-Based Solid-Phase Strategy.

Authors:  Wentao Chen; Jiajia Dong; Suhua Li; Yu Liu; Yujia Wang; Leonard Yoon; Peng Wu; K Barry Sharpless; Jeffery W Kelly
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-22       Impact factor: 15.336

6.  Bifluoride-catalysed sulfur(VI) fluoride exchange reaction for the synthesis of polysulfates and polysulfonates.

Authors:  Bing Gao; Linda Zhang; Qinheng Zheng; Feng Zhou; Liana M Klivansky; Jianmei Lu; Yi Liu; Jiajia Dong; Peng Wu; K Barry Sharpless
Journal:  Nat Chem       Date:  2017-06-19       Impact factor: 24.427

7.  Multidimensional SuFEx Click Chemistry: Sequential Sulfur(VI) Fluoride Exchange Connections of Diverse Modules Launched From An SOF4 Hub.

Authors:  Suhua Li; Peng Wu; John E Moses; K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-06       Impact factor: 15.336

8.  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

9.  Arylfluorosulfates Inactivate Intracellular Lipid Binding Protein(s) through Chemoselective SuFEx Reaction with a Binding Site Tyr Residue.

Authors:  Wentao Chen; Jiajia Dong; Lars Plate; David E Mortenson; Gabriel J Brighty; Suhua Li; Yu Liu; Andrea Galmozzi; Peter S Lee; Jonathan J Hulce; Benjamin F Cravatt; Enrique Saez; Evan T Powers; Ian A Wilson; K Barry Sharpless; Jeffery W Kelly
Journal:  J Am Chem Soc       Date:  2016-06-02       Impact factor: 15.419

10.  SuFEx Click Chemistry Enabled Late-Stage Drug Functionalization.

Authors:  Zilei Liu; Jie Li; Suhua Li; Gencheng Li; K Barry Sharpless; Peng Wu
Journal:  J Am Chem Soc       Date:  2018-02-16       Impact factor: 15.419

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