ArticleJournal of the American Chemical Society2022
Catalytic Chemo-, Regio-, Diastereo-, and Enantioselective Bromochlorination of Unsaturated Systems Enabled by Lewis Base-Controlled Chloride Release.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Internally Directed Stereochemical Alteration of Alkene Dihalogenation.The Journal of organic chemistry · 2026Article
- Enriching AlkeneOrganic letters · 2026Article
- Lewis Base-Catalyzed Interhalogenation of Terminal Allenes: Selective Strategy for Accessing Vicinal Vinylic, Allylic Heterodihalides.Organic letters · 2025Article
- 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
- Diastereodivergent nucleophile-nucleophile alkene chlorofluorination.Nature chemistry · 2024Article
- Practical and regioselective halonitrooxylation of olefins to access β-halonitrates.Nature communications · 2024Article
- Stereospecific syn-dihalogenations and regiodivergent syn-interhalogenation of alkenes via vicinal double electrophilic activation strategy.Nature communications · 2024Article
- Regioselective Electrophilic Addition to Propargylic B(MIDA)s Enabled by β-Boron Effect.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- Synthesis of a Bench-Stable Manganese(III) Chloride Compound: Coordination Chemistry and Alkene Dichlorination.Journal of the American Chemical Society · 2022Article
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Authors and funding
4 authors.
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Abstract
A new strategy is described for the Lewis base-catalyzed bromochlorination of unsaturated systems that is mechanistically distinct from prior methodologies. The novelty of this method hinges on the utilization of thionyl chloride as a latent chloride source in combination with as little as 1 mol % of triphenylphosphine or triphenylphosphine oxide as Lewis basic activators. This metal-free, catalytic chemo-, regio-, and diastereoselective bromochlorination of alkenes and alkynes exhibits excellent site selectivity in polyunsaturated systems and provides access to a wide variety of vicinal bromochlorides with up to >20:1 regio- and diastereoselectivity. The precision installation of Br, Cl, and I in various combinations is also demonstrated by simply varying the commercial halogenating reagents employed. Notably, when a chiral Lewis base promoter is employed, an enantioselective bromochlorination of chalcones is possible with up to a 92:8 enantiomeric ratio when utilizing only 1-3 mol % of (DHQD)
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