ArticleNature chemistry2020
Chemoselective oxidative generation of ortho-quinone methides and tandem transformations.
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 12 papers.
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Who cites it
12 citing papers in PubMed, 93 citations in OpenAlex.
- Ortho-Alkynyl Quinone Methides as Privileged Intermediates in Synthesis of Polycyclic Frameworks: A Short Review.Chemical record (New York, N.Y.) · 2026Review
- Recent Breakthroughs in Cyclizations ofMolecules (Basel, Switzerland) · 2026Review
- Ultrafast Formation of Aza-Quinone Methides from Suitably SubstitutedJournal of the American Chemical Society · 2026Article
- Pyrene-based conjugated porous polymers as photocatalysts for oxidative cycloaddition of phenols.Chemical science · 2026Article
- Moscatilin, a potential therapeutic agent for cancer treatment: insights into molecular mechanisms and clinical prospects.Medical oncology (Northwood, London, England) · 2024Review
- One-Pot Synthesis of 3,4-Dihydrocoumarins via C-H Oxidation/Conjugate Addition/Cyclization Cascade Reaction.Molecules (Basel, Switzerland) · 2023Article
- Selective radical cascade (4+2) annulation with olefins towards the synthesis of chroman derivativesChemical science · 2022Article
- Hypoiodite-Catalyzed Oxidative Umpolung of Indoles for Enantioselective Dearomatization.Journal of the American Chemical Society · 2022Article
- A cascade double 1,4-addition/intramolecular annulation strategy for expeditious assembly of unsymmetrical dibenzofurans.Communications chemistry · 2021Article
- Cross dehydrogenative C-O coupling catalysed by a catenane-coordinated copper(i).Chemical science · 2020Article
- Synergistic Ammonium (Hypo)Iodite/Imine Catalysis for the Asymmetric α-Hydroxylation of β-Ketoesters.Organic letters · 2020Article
- Mild map to quinone methides.Nature chemistry · 2020Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
ortho-Quinone methides are useful transient synthetic intermediates in organic synthesis. These species are most often generated in situ by the acid- or base-mediated transformation of phenols that have been pre-functionalized at a benzylic position, or by biomimetic oxidation of the corresponding ortho-alkylphenols with metal oxidants or transition-metal complexes. Here we describe a method for the transition-metal-free oxidative generation of o-QMs from ortho-alkylarenols, using hypoiodite catalysis under nearly neutral conditions, which can then be applied in one-pot tandem reactions. This method for the chemoselective oxidative generation of ortho-quinone methides may prove superior to previous methods with respect to environmental issues and scope, and can be applied to various tandem reactions such as inter- or intramolecular [4 + 2] cycloaddition, oxa-6π-electrocyclization, conjugate addition and spiroepoxidation.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.