ArticleJournal of the American Chemical Society2019
Catalytic Ring Expansions of Cyclic Alcohols Enabled by Proton-Coupled Electron Transfer.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed.
- Deoxygenative Olefin Insertion of Cyclic Alcohols Promoted by Sulfoxide Cation Radicals.Journal of the American Chemical Society · 2026Article
- Photocatalytic multicomponent alkene dicarbofunctionalizationChemical science · 2026Article
- Organo-catalyzed photoelectrochemical ring-contraction of arylidenecyclobutanolsChemical science · 2026Article
- Deconstructive Radical-Radical Coupling for Programmable Remote Acylation.Angewandte Chemie (International ed. in English) · 2025Article
- Light-Driven C(spAccounts of chemical research · 2025Article
- Ring Expansions of 1,2-Amino Alcohols to Amine Heterocycles Enabled by Proton-Coupled Electron Transfer.Journal of the American Chemical Society · 2025Article
- Organic photoredox-catalyzed unimolecular PCET of benzylic alcohols.Chemical science · 2025Article
- Accessing Alkoxy Radicals via Frustrated Radical Pairs: Diverse Oxidative Functionalizations of Tertiary Alcohols.Journal of the American Chemical Society · 2024Article
- Methyl Ketones as Alkyl Halide Surrogates: A Deacylative Halogenation Approach for Strategic Functional Group Conversions.Journal of the American Chemical Society · 2023Article
- Enantioselective Addition of Remote Alkyl Radicals to Double Bonds by Photocatalytic Proton-Coupled Electron Transfer (PCET) Deconstruction of Unstrained Cycloalkanols.Organic letters · 2022Article
- Biocatalytic One-Carbon Ring Expansion of Aziridines to Azetidines via a Highly Enantioselective [1,2]-Stevens Rearrangement.Journal of the American Chemical Society · 2022Article
- Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.Chemical reviews · 2022Review
- Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis.Chemical reviews · 2022Review
- Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction.Angewandte Chemie (International ed. in English) · 2021Review
- 1,3-Alkyl Transposition in Allylic Alcohols Enabled by Proton-Coupled Electron Transfer.Angewandte Chemie (International ed. in English) · 2021Article
- Tuning the reactivity of alkoxyl radicals from 1,5-hydrogen atom transfer to 1,2-silyl transfer.Nature communications · 2021Article
- Catalytic generation of alkoxy radicals from unfunctionalized alcohols.Chemical science · 2020Review
- Transition Metal-Mediated C-C Single Bond Cleavage: Making the Cut in Total Synthesis.Angewandte Chemie (International ed. in English) · 2020Review
- C-C Bond Cleavage Approach to Complex Terpenoids: Development of a Unified Total Synthesis of the Phomactins.Journal of the American Chemical Society · 2020Article
- Discoveries and Challenges en Route to Swinhoeisterol A.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
We report here a catalytic method for the modular ring expansion of cyclic aliphatic alcohols. In this work, proton-coupled electron transfer activation of an allylic alcohol substrate affords an alkoxy radical intermediate that undergoes subsequent C-C bond cleavage to furnish an enone and a tethered alkyl radical. Recombination of this alkyl radical with the revealed olefin acceptor in turn produces a ring-expanded ketone product. The regioselectivity of this C-C bond-forming event can be reliably controlled via substituents on the olefin substrate, providing a means to convert a simple N-membered ring substrate to either n+1 or n+2 ring adducts in a selective fashion.
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