ArticleNature chemistry2020
Dual electrocatalysis enables enantioselective hydrocyanation of conjugated alkenes.
Article in Nature chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 67 papers.
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Who cites it
67 citing papers in PubMed, 293 citations in OpenAlex.
- Electrochemically Driven Regioselective Radical Functionalization of Allenes: Scope and Mechanistic Insights.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Heterogeneous Indirect Redox Electrocatalysis in Electrolyte.Advanced materials (Deerfield Beach, Fla.) · 2026Review
- Recent Advances in the High-Value Conversion of Alkenes Induced by Electrochemistry.Molecules (Basel, Switzerland) · 2026Review
- Electrochemical hydroxylation of alkenes with HNational science review · 2026Article
- Tunable enantioselective electrocatalytic functionalization of unactivated alkenes.Nature communications · 2026Article
- Unveiling mechanistic patterns of copper-catalyzed radical bond formation through linear free energy relationship.Nature communications · 2025Article
- One-Electron Approach for Trans-Selective Alkyne Semi-Reduction via Cobalt Catalysis.Journal of the American Chemical Society · 2025Article
- Silylative Amide to Nitrile Conversion Mediated by Simple Lanthanide-Organoamides: Scope and Mechanism.Angewandte Chemie (International ed. in English) · 2025Article
- Bimetallic [Co/K] hydrogen evolution catalyst for electrochemical terminal C-H functionalization.Nature communications · 2025Article
- Electrochemical Enantioselective Oxidation of Indoles via Chiral Phosphoric Acid Catalysis in Cooperation with HAngewandte Chemie (International ed. in English) · 2025Article
- Asymmetric cyanoesterification of vinylarenes by electrochemical copper catalysis.Nature communications · 2025Article
- Article
- Markovnikov-Selective Electrocatalytic Hydroalkylation Enabled by Metal-Ligand Cooperative Storage of H-Atom Equivalents.ACS catalysis · 2025Article
- Cathodic oxygen reduction-enabled rhodium-catalyzed (5 + 1) C-H/O-H annulation inspired by fuel cells.Nature communications · 2025Article
- Enantioselective electrochemical nickel-catalyzed vinylogous radical reactions.Science advances · 2025Article
- Remote Migratory Reductive Arylation of Unactivated Alkenes Enabled by Electrochemical Nickel Catalysis.ChemSusChem · 2025Article
- Recent advances in electrochemical copper catalysis for modern organic synthesis.Beilstein journal of organic chemistry · 2025Review
- Carbon isotopic labelling of carboxylic acids enabled by organic photoredox-catalysed cyanation.Nature synthesis · 2025Article
- Enantioconvergent Cross-Nucleophile Coupling: Copper-Catalyzed Deborylative Cyanation.Angewandte Chemie (International ed. in English) · 2024Article
- Overcoming Copper Reduction Limitation in Asymmetric Substitution: Aryl-Radical-Enabled Enantioconvergent Cyanation of Alkyl Iodides.Journal of the American Chemical Society · 2024Article
7 more citing papers are in PubMed but not listed here.
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
Abstract
Chiral nitriles and their derivatives are prevalent in pharmaceuticals and bioactive compounds. Enantioselective alkene hydrocyanation represents a convenient and efficient approach for synthesizing these molecules. However, a generally applicable method featuring a broad substrate scope and high functional group tolerance remains elusive. Here, we address this long-standing synthetic problem using dual electrocatalysis. Using this strategy, we leverage electrochemistry to seamlessly combine two canonical radical reactions-cobalt-mediated hydrogen-atom transfer and copper-promoted radical cyanation-to accomplish highly enantioselective hydrocyanation without the need for stoichiometric oxidants. We also harness electrochemistry's unique feature of precise potential control to optimize the chemoselectivity of challenging substrates. Computational analysis uncovers the origin of enantio-induction, for which the chiral catalyst imparts a combination of attractive and repulsive non-covalent interactions to direct the enantio-determining C-CN bond formation. This work demonstrates the power of electrochemistry in accessing new chemical space and providing solutions to pertinent challenges in synthetic chemistry.
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