ArticleAngewandte Chemie (International ed. in English)2022
Accelerated SuFEx Click Chemistry For Modular Synthesis.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 40 papers.
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Who cites it
40 citing papers in PubMed, 117 citations in OpenAlex.
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- Comprehensive Reinvestigation of Carbodiimide Guanylation: HCl-Initiated Access to Tri- and Tetrasubstituted Guanidines.ACS omega · 2026Article
- Chemical Strategies for Controlling Sulfation in Biomacromolecules.ACS chemical biology · 2026Review
- Ruthenium-Catalyzed CH Alkenylation of Trypanocidal Naphthoquinones: A Mechanistic Benchmarking Study.ChemistryOpen · 2026Article
- Polysulfamates as "Macroisosteres" of Polyurethanes with Improved Degradability.Angewandte Chemie (International ed. in English) · 2025Article
- Disubstituted Meldrum's Acid: Another Scaffold with SuFEx-like Reactivity.Molecules (Basel, Switzerland) · 2025Article
- Multimodal S(VI) Exchange Click Reactions Derived from SFThe Journal of organic chemistry · 2025Article
- Guanidium Unmasked: Repurposing Common Amide Coupling Reagents for the Synthesis of Pentasubstituted Guanidine Bases.The Journal of organic chemistry · 2025Article
- Switching Residues: A Platform for the Synthesis of Fidaxomicin Antibiotics.Angewandte Chemie (International ed. in English) · 2025Article
- Diversity Oriented Clicking for Modular Synthesis.Nature reviews. Methods primers · 2025Article
- Lewis Acid-Catalyzed Sulfur Fluoride Exchange.Organic letters · 2024Article
- Benzene-1,3-disulfonyl fluoride and Benzene-1,3,5-trisulfonyl fluoride: Low-Cost, Stable, and Selective Reagents for SuFEx-Driven Deoxyazidation.Advanced synthesis & catalysis · 2024Article
- SONature communications · 2024Article
- Intramolecular chalcogen bonding activated SuFEx click chemistry for efficient organic-inorganic linking.Nature communications · 2024Article
- Article
- Iterative SuFEx approach for sequence-regulated oligosulfates and its extension to periodic copolymers.Nature communications · 2024Article
- Protocol for producing phosphoramidate using phosphorus fluoride exchange click chemistry.STAR protocols · 2024Article
- Modular synthesis of functional libraries by accelerated SuFEx click chemistry.Chemical science · 2024Article
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
Abstract
SuFEx click chemistry is a powerful method designed for the selective, rapid, and modular synthesis of functional molecules. Classical SuFEx reactions form stable S-O linkages upon exchange of S-F bonds with aryl silyl-ether substrates, and while near-perfect in their outcome, are sometimes disadvantaged by relatively high catalyst loadings and prolonged reaction times. We herein report the development of accelerated SuFEx click chemistry (ASCC), an improved SuFEx method for the efficient and catalytic coupling of aryl and alkyl alcohols with a range of SuFExable hubs. We demonstrate Barton's hindered guanidine base (2-tert-butyl-1,1,3,3-tetramethylguanidine; BTMG) as a superb SuFEx catalyst that, when used in synergy with silicon additive hexamethyldisilazane (HMDS), yields stable S-O bond linkages in a single step; often within minutes. The powerful combination of BTMG and HMDS reagents allows for catalyst loadings as low as 1.0 mol % and, in congruence with click-principles, provides a scalable method that is safe, efficient, and practical for modular synthesis. ASSC expands the number of accessible SuFEx products and will find significant application in organic synthesis, medicinal chemistry, chemical biology, and materials science.
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Registered trials
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