ArticleACS catalysis2019
Mn-Catalyzed Electrochemical Chloroalkylation of Alkenes.
Article in ACS catalysis, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- Chloroalkylation of Unactivated Alkenes via a Cobalt-Mediated Radical Ligand Transfer (RLT) Photoredox Catalysis Platform.JACS Au · 2025Article
- Review
- Kharasch-Type Haloalkylation of Alkenes by Photoinduced Copper Catalysis.Journal of the American Chemical Society · 2025Article
- Electrochemical Late-Stage Functionalization.Chemical reviews · 2023Review
- Controlling Selectivity in Shuttle Hetero-difunctionalization Reactions: Electrochemical Transfer Halo-thiolation of Alkynes.Angewandte Chemie (International ed. in English) · 2023Article
- Electro-Synthesis of Organic Compounds with Heterogeneous Catalysis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2022Review
- Nickel-catalyzed switchable asymmetric electrochemical functionalization of alkenes.Science advances · 2022Article
- Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates.Beilstein journal of organic chemistry · 2022Article
- Electrocatalysis as an enabling technology for organic synthesis.Chemical Society reviews · 2021Article
- Linear Paired Electrolysis-Realising 200 % Current Efficiency for Stoichiometric Transformations-The Electrochemical Bromination of Alkenes.Angewandte Chemie (International ed. in English) · 2021Article
- Direct Oxidation of Aryl Malononitriles Enabling a Copper-Catalyzed Intermolecular Alkene Carbochlorination.Organic letters · 2021Article
- Review
- Electroreductive Carbofunctionalization of Alkenes with Alkyl Bromides via a Radical-Polar Crossover Mechanism.Journal of the American Chemical Society · 2020Article
- New Redox Strategies in Organic Synthesis by Means of Electrochemistry and Photochemistry.ACS central science · 2020Review
- Dual electrocatalysis enables enantioselective hydrocyanation of conjugated alkenes.Nature chemistry · 2020Article
- Catalyzing Electrosynthesis: A Homogeneous Electrocatalytic Approach to Reaction Discovery.Accounts of chemical research · 2020Review
- Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals.Organic letters · 2019Article
- New Bisoxazoline Ligands Enable Enantioselective Electrocatalytic Cyanofunctionalization of Vinylarenes.Journal of the American Chemical Society · 2019Article
- Electrochemical Alkoxysulfonylation Difunctionalization of Styrene Derivatives Using Sodium Sulfinates as Sulfonyl Sources.ACS omega · 2019Article
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6 authors.
Funding
Abstract
The heterodifunctionalization of alkenes is an efficient method for synthesizing highly functionalized organic molecules. In this report, we describe the use of anodically coupled electrolysis for the catalytic chloroalkylation of alkenes-a reaction that constructs vicinal C-C and C-Cl bonds in a single synthetic operation-from malononitriles or cyanoacetates and NaCl. Knowledge of the persistent radical effect guided the reaction design and development. A series of controlled experiments, including divided-cell electrolysis that compartmentalized the anodic and cathodic events, allowed us to identify the key radical intermediates and the pathway to their electrocatalytic formation. Cyclic voltammetry data further support the proposed mechanism entailing the parallel, Mn-mediated generation of two radical intermediates in an anodically coupled electrolysis followed by their selective addition to the alkene.
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