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.
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| http://dx.doi.org/10.1002/anie.201403758 | DOI Listing |
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SuFEx-based chemical diversification for the systematic discovery of CRBN molecular glues.
Bioorg Med Chem
April 2024
Department of Chemistry, The Scripps Research Institute, United States.
Article Synopsis
- Molecular glues are small molecules that stabilize protein interactions and are gaining traction for drug development, particularly for targeted protein degradation, despite lacking the design principles seen in other methods like PROTACs.
- Researchers modified the CRBN ligand, 5'-amino lenalidomide, to change its target specificity using a method called sulfur(VI)-fluoride exchange (SuFEx), successfully creating over 3,000 analogs.
- Among the screened compounds, four were identified that effectively degrade the G-to-S phase transition 1 (GSPT1) protein, showcasing the potential for discovering new CRBN molecular glues through SuFEx techniques.
Sulfur(vi) fluoride exchange chemistry has been reported to be effective at synthesizing valuable sulfur(vi) functionalities through sequential nucleophilic additions, yet oxygen-based nucleophiles are limited in this approach to phenolic derivatives. Herein, we report a new sulfur(iv) fluoride exchange strategy to access synthetically challenging substituted sulfamate esters from alkyl alcohols and amines. We also report the development of a non-gaseous, sulfur(iv) fluoride exchange reagent, -methylimidazolium sulfinyl fluoride hexafluorophosphate (MISF).
View Article and Find Full Text PDFSuFExable polymers with helical structures derived from thionyl tetrafluoride.
Nat Chem
September 2021
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, CA, USA.
Sulfur(VI) fluoride exchange (SuFEx) is a category of click chemistry that enables covalent linking of modular units through sulfur(VI) connective hubs. The efficiency of SuFEx and the stability of the resulting bonds have led to polymer chemistry applications. Now, we report the SuFEx click chemistry synthesis of several structurally diverse SOF-derived copolymers based on the polymerization of bis(iminosulfur oxydifluorides) and bis(aryl silyl ethers).
View Article and Find Full Text PDFBifluoride Ion Mediated SuFEx Trifluoromethylation of Sulfonyl Fluorides and Iminosulfur Oxydifluorides.
Angew Chem Int Ed Engl
March 2019
La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC, 3086, Australia.
SuFEx is a new-generation click chemistry transformation that exploits the unique properties of S-F bonds and their ability to undergo near-perfect reactions with nucleophiles. We report here the first SuFEx-based procedure for the efficient synthesis of pharmaceutically important triflones and bis(trifluoromethyl)sulfur oxyimines from sulfonyl fluorides and iminosulfur oxydifluorides, respectively. The new process involves rapid S-F exchange with trifluoromethyltrimethylsilane (TMSCF ) upon activation by potassium bifluoride in anhydrous DMSO.
View Article and Find Full Text PDFSuFEx-based synthesis of polysulfates.
Angew Chem Int Ed Engl
September 2014
Department of Chemistry The Scripps Research Institute La Jolla, CA 92037 (USA).
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.
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