ArticleNature communications2023
Organomediated electrochemical fluorosulfonylation of aryl triflates via selective C-O bond cleavage.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Nickel-Catalyzed Asymmetric α-Alkenylations of Acyclic Amides that Provide Tertiary Stereocenters.Journal of the American Chemical Society · 2025Article
- Electrochemically promoted defluorinative sulfoximination and fluorosulfonylation of non-activated aryl fluorides at room temperature.Chemical science · 2025Article
- Electrochemical Conversions of Sulfenamides into Sulfonimidoyl- and Sulfondiimidoyl Fluorides.JACS Au · 2025Article
- Electroreductive deuteroarylation of alkenes enabled by an organo-mediator.Chemical science · 2024Article
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Authors and funding
9 authors.
Funding
Abstract
Although aryl triflates are essential building blocks in organic synthesis, the applications as aryl radical precursors are limited. Herein, we report an organomediated electrochemical strategy for the generation of aryl radicals from aryl triflates, providing a useful method for the synthesis of aryl sulfonyl fluorides from feedstock phenol derivatives under very mild conditions. Mechanistic studies indicate that key to success is to use catalytic amounts of 9, 10-dicyanoanthracene as an organic mediator, enabling to selectively active aryl triflates to form aryl radicals via orbital-symmetry-matching electron transfer, realizing the anticipated C-O bond cleavage by overcoming the competitive S-O bond cleavage. The transition-metal-catalyst-free protocol shows good functional group tolerance, and may overcome the shortages of known methods for aryl sulfonyl fluoride synthesis. Furthermore, this method has been used for the modification and formal synthesis of bioactive molecules or tetraphenylethylene (TPE) derivative with improved quantum yield of fluorescence.
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Registered trials
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