ArticleNature communications2021
Generation of non-stabilized alkyl radicals from thianthrenium salts for C-B and C-C bond formation.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Formal Markovnikov Hydroazolation of Alkenes via Reductive Activation of Alkylthianthrenium Salts.Journal of the American Chemical Society · 2026Article
- Alkoxysulfonium Salts Unlock Access to New Aryl Sulfonium Salts for Cross-Coupling.Angewandte Chemie (International ed. in English) · 2026Article
- Homologative alkene difunctionalization.Nature chemistry · 2026Article
- Photoinduced Deoxygenative Boration of Unactivated Alcohols Involving In-Situ-Formed Alkyl Iodides.Organic letters · 2025Article
- Unlocking azole chemical space via modular and regioselective N-alkylation.Nature chemistry · 2025Article
- Persistent Boryl Radicals as Highly Reducing Photoredox Catalysts for Debrominative Borylations.Journal of the American Chemical Society · 2025Article
- Indirect Anti-Markovnikov Hydrofunctionalization of Terminal Alkenes via an Alkenyl Thianthrenium Intermediate.Angewandte Chemie (International ed. in English) · 2025Article
- Allenyl Thianthrenium Salt: A Bench-Stable CJournal of the American Chemical Society · 2024Article
- Orthogonal bioconjugation targeting cysteine-containing peptides and proteins using alkyl thianthrenium salts.Nature communications · 2024Article
- Metallaphotoredox deuteroalkylation utilizing thianthrenium salts.Nature communications · 2024Article
- Dinuclear gold-catalyzed divergent dechlorinative radical borylation of gem-dichloroalkanes.Nature communications · 2024Article
- Unified metal-free intermolecular Heck-type sulfonylation, cyanation, amination, amidation of alkenes by thianthrenation.Nature communications · 2024Article
- Nucleophilic functionalization of thianthrenium salts under basic conditions.Beilstein journal of organic chemistry · 2024Article
- Sulfonium Salts as Acceptors in Electron Donor-Acceptor Complexes.Angewandte Chemie (International ed. in English) · 2023Review
- Diastereoselective Synthesis of Cyclopropanes from Carbon Pronucleophiles and Alkenes.Angewandte Chemie (International ed. in English) · 2023Article
- Organothianthrenium salts: synthesis and utilization.Chemical science · 2022Review
- Photocatalytic C(spChemical science · 2022Review
- A general electron donor-acceptor complex for photoactivation of arenesChemical science · 2022Article
- Metal-free allylic C-H nitrogenation, oxygenation, and carbonation of alkenes by thianthrenation.Chemical science · 2022Article
- Base-Mediated Radical Borylation of Alkyl Sulfones.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Sulfonium salts bearing a positively charged sulfur atom with three organic substituents have intrigued chemists for more than a century for their unusual structures and high chemical reactivity. These compounds are known to undergo facile single-electron reduction to emerge as a valuable and alternative source of aryl radicals for organic synthesis. However, the generation of non-stabilized alkyl radicals from sulfonium salts has been a challenge for several decades. Here we report the treatment of S-(alkyl) thianthrenium salts to generate non-stabilized alkyl radicals as key intermediates granting the controlled and selective outcome of the ensuing reactions under mild photoredox conditions. The value of these reagents has been demonstrated through the efficient construction of alkylboronates and other transformations, including heteroarylation, alkylation, alkenylation, and alkynylation. The developed method is practical, and provides the opportunity to convert C-OH bond to C-B and C-C bonds.
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