ArticleScience advances2018
Electrochemical oxidative oxysulfenylation and aminosulfenylation of alkenes with hydrogen evolution.
Article in Science advances, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 136 citations in OpenAlex.
- Modular Access to α-Tertiary Amines: Electrochemical Tandem Di-Functionalization of Olefins With Ammonia Surrogates and Amino Acids.Angewandte Chemie (International ed. in English) · 2026Article
- Potassium thiocyanate-promoted four-component alkoxysulfenylation of styrenes with imidazo[1,2-RSC advances · 2026Article
- Electrochemically Driven Nickel-Catalyzed Enantioselective Hydro-Arylation/Alkenylation of Enones.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Harnessing Bromo/Acyloxy Transposition (BrAcT) and Excited-State Copper Catalysis for Styrene Difunctionalization.Journal of the American Chemical Society · 2024Article
- Aminothiolation of alkenes with azoles and Bunte salts.Frontiers in chemistry · 2023Article
- Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.Chemical reviews · 2022Review
- Electrochemical organic reactions: A tutorial review.Frontiers in chemistry · 2022Review
- Alkoxysulfenylation of alkenes: development and recent advances.RSC advances · 2021Review
- Electrochemical C-C bond cleavage of cyclopropanes towards the synthesis of 1,3-difunctionalized molecules.Nature communications · 2021Article
- Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions.Molecules (Basel, Switzerland) · 2020Review
- Electroreductive Carbofunctionalization of Alkenes with Alkyl Bromides via a Radical-Polar Crossover Mechanism.Journal of the American Chemical Society · 2020Article
- Visible Light-Driven Cascade Carbon-Carbon Bond Scission for Organic Transformations and Plastics Recycling.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2019Article
- Enantioselective, Lewis Base-Catalyzed, Intermolecular Sulfenoamination of Alkenes.Journal of the American Chemical Society · 2019Article
- Electrochemical Alkoxysulfonylation Difunctionalization of Styrene Derivatives Using Sodium Sulfinates as Sulfonyl Sources.ACS omega · 2019Article
- Electrochemical oxidative C-H/S-H cross-coupling between enamines and thiophenols with HChemical science · 2019Article
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Corrections and comments
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Difunctionalization of alkenes is a valuable and versatile chemical transformation that could quickly build complex molecules. Extensive efforts have been made, and great achievement, such as Sharpless aminohydroxylation and dihydroxylation, has been reached. However, in marked contrast to the extensive research of aminohydroxylation and dihydroxylation, directly using thiophenols/thiols and O/N-nucleophiles to perform the difunctionalization of alkenes that form the C-S and C-O/N bonds together is still underexplored. The main issue is that thiophenols/thiols are often easily overoxidized to sulfoxides or sulphones under such essential oxidation conditions. We demonstrate an electrochemical oxidative oxysulfenylation and aminosulfenylation of alkenes. A critical feature of this transformation is that neither external chemical oxidants nor metal catalysts are required. This electrochemical oxidative synthetic strategy could also be applied for the hydroxysulfenylation and acyloxysulfenylation of alkenes.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.