ArticleNature communications2021
Electrochemical C-C bond cleavage of cyclopropanes towards the synthesis of 1,3-difunctionalized molecules.
Article in Nature communications, 2021. 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.
- Programmable divergent electrochemical ring-opening multifunctionalization of strained rings.Nature chemistry · 2026Article
- Controllable site-selective C-C bond cleavage for the divergent synthesis of imidazo[1,5-RSC advances · 2025Article
- Electro-oxidative amination of benzylic C(sp³)-C(sp³) bonds in aromatic hydrocarbons.Nature communications · 2025Article
- Strain-Release-Driven Electrochemical Skeletal Rearrangement of Non-Biased Alkyl Cyclopropanes/Butanes.Angewandte Chemie (International ed. in English) · 2025Article
- Electrochemical Deconstructive Methoxylation of Arylalcohols-A Synthetic and Mechanistic Investigation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Selective monodeuteration enabled by bisphosphonium catalyzed ring opening processes.Nature communications · 2024Article
- Electrochemical Synthesis of C(spOrganic letters · 2024Article
- Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent.Nature communications · 2024Article
- Oxidatively-induced C(spChemical science · 2024Article
- A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis.Beilstein journal of organic chemistry · 2024Review
- Divergent Synthesis of β-Fluoroamides via Silver-Catalyzed Oxidative Deconstruction of Cyclopropanone Hemiaminals.Organic letters · 2023Article
- Remote Radical 1,3-, 1,4-, 1,5-, 1,6- and 1,7-Difunctionalization Reactions.Molecules (Basel, Switzerland) · 2023Review
- Deconstructive Functionalization of Unstrained Cycloalkanols via Electrochemically Generated Aromatic Radical Cations.Organic letters · 2023Article
- Electroreductively Induced Radicals for Organic Synthesis.Molecules (Basel, Switzerland) · 2023Review
- Radical hydrodifluoromethylation of unsaturated C-C bonds via an electroreductively triggered two-pronged approach.Communications chemistry · 2022Article
- Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives.Beilstein journal of organic chemistry · 2022Article
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Authors and funding
8 authors.
Funding
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Abstract
Electrochemistry has a lot of inherent advantages in organic synthesis and many redox reactions have been achieved under electrochemical condition. However, the electrochemical C-C bond cleavage and functionalization reactions are less studied. Here we develop electrochemical C-C bond cleavage and 1,3-difuntionalization of arylcyclopropanes under catalyst-free and external-oxidant-free conditions. 1,3-difluorination, 1,3-oxyfluorination and 1,3-dioxygenation of arylcyclopropanes are achieved with a high chemo- and regioselectivity by the strategic choice of nucleophiles. This protocol has good functional groups tolerance and can be scaled up. Mechanistic studies demonstrate that arylcyclopropane radical cation obtained from the anode oxidation and the subsequently generated benzyl carbonium are the key intermediates in this transformation. This development provides a scenario for constructing 1,3-difunctionalized molecules.
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