ArticleNature chemistry2014
Catalytic, stereospecific syn-dichlorination of alkenes.
Article in Nature chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 35 papers.
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Who cites it
35 citing papers in PubMed, 206 citations in OpenAlex.
- Internally Directed Stereochemical Alteration of Alkene Dihalogenation.The Journal of organic chemistry · 2026Article
- Enriching AlkeneOrganic letters · 2026Article
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- Halodealkenylation: Ozonolysis and Catalytic FeOrganic letters · 2024Article
- Stereospecific syn-dichlorination of allylic amines enabled by identification of a superior stereo-directing group.Communications chemistry · 2024Article
- Visible-Light-Mediated Vicinal Dihalogenation of Unsaturated C-C Bonds Using Dual-Functional Group Transfer Reagents.Journal of the American Chemical Society · 2024Article
- Intermolecular Aza-Wacker Coupling of Alkenes with Azoles by Photo-Aerobic Selenium-π-Acid Multicatalysis.ACS catalysis · 2024Article
- Stereospecific syn-dihalogenations and regiodivergent syn-interhalogenation of alkenes via vicinal double electrophilic activation strategy.Nature communications · 2024Article
- Catalytic 1,1-diazidation of alkenes.Nature communications · 2024Article
- Intramolecular chaperone-assisted dual-anchoring activation (ICDA): a suitable preorganization for electrophilic halocyclization.Chemical science · 2024Article
- Tuning light-driven oxidation of styrene inside water-soluble nanocages.Nature communications · 2024Article
- Photocatalytic, modular difunctionalization of alkenes enabled by ligand-to-metal charge transfer and radical ligand transfer.Chemical science · 2023Article
- Reactive Chlorine Capture by Dichlorination of Alkene Linkers in Metal-Organic Frameworks.ACS applied materials & interfaces · 2022Article
- Hydrogen-Bond-Modulated Nucleofugality of SeAngewandte Chemie (International ed. in English) · 2022Article
- The Electrochemical cis-Chlorination of Alkenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Lewis Base Catalyzed, Sulfenium Ion Initiated Enantioselective, Spiroketalization Cascade.The Journal of organic chemistry · 2021Article
- Oxoammonium salts are catalysing efficient and selective halogenation of olefins, alkynes and aromatics.Nature communications · 2021Article
- Selenophosphoramide-catalyzed diamination and oxyamination of alkenes.Chemical science · 2020Article
- Natural Compounds and Their Structural Analogs in Regio- and Stereoselective Synthesis of New Families of Water-Soluble 2Molecules (Basel, Switzerland) · 2020Article
- Catalytic, EnantioselectiveJournal of the American Chemical Society · 2019Article
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3 authors at 1 institution in 1 country.
Funding
Abstract
As some of the oldest organic chemical reactions known, the ionic additions of elemental halogens such as bromine and chlorine to alkenes are prototypical examples of stereospecific reactions, typically delivering vicinal dihalides resulting from anti-addition. Although the invention of enantioselective variants is an ongoing challenge, the ability to overturn the intrinsic anti-diastereospecificity of these transformations is also a largely unsolved problem. Here, we describe the first catalytic, syn-stereospecific dichlorination of alkenes, employing a group transfer catalyst based on a redox-active main group element (selenium). With diphenyl diselenide (PhSeSePh) (5 mol%) as the pre-catalyst, benzyltriethylammonium chloride (BnEt3NCl) as the chloride source and an N-fluoropyridinium salt as the oxidant, a wide variety of functionalized cyclic and acyclic 1,2-disubstituted alkenes, including simple allylic alcohols, deliver syn-dichlorides with exquisite stereocontrol. This methodology is expected to find applications in streamlining the synthesis of polychlorinated natural products such as the chlorosulfolipids.
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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.