ArticleNature communications2017
Dehydrogenative desaturation-relay via formation of multicenter-stabilized radical intermediates.
Article in Nature communications, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
What it found
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Who cites it
17 citing papers in PubMed.
- A Copper-Catalyzed Decarboxylative Olefination Cascade Enables Access to Protoberberine Alkaloid Frameworks.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Site-Selective Benzylic Dehydrogenation of Alkylindoles.JACS Au · 2025Article
- Copper-Catalyzed Cyclization and Alkene Transposition Cascade Enables a Modular Synthesis of Complex Spirocyclic Ethers.Journal of the American Chemical Society · 2025Article
- One-Pot Sequential Synthesis of Alkenylated Dihydroquinolinones and Hexahydroacridinones in Deep Eutectic Solvent Medium.ACS omega · 2024Article
- Dehydrogenative synthesis ofScience advances · 2024Article
- Comprehensive Mechanistic Analysis of Palladium- and Nickel-Catalyzed α,β-Dehydrogenation of Carbonyls via Organozinc Intermediates.The Journal of organic chemistry · 2024Article
- Asymmetric Synthesis of Nidulalin A and Nidulaxanthone A: Selective Carbonyl Desaturation Using an Oxoammonium Salt.Journal of the American Chemical Society · 2024Article
- Synthesis of 1,3-Dienes via Ligand-Enabled Sequential Dehydrogenation of Aliphatic Acids.Journal of the American Chemical Society · 2023Article
- Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes.The Journal of organic chemistry · 2023Article
- Multiple remote C(spChemical science · 2022Article
- Selective desaturation of amides: a direct approach to enamides.Chemical science · 2022Article
- A Desaturative Approach for Aromatic Aldehyde Synthesis via Synergistic Enamine, Photoredox and Cobalt Triple Catalysis.Angewandte Chemie (International ed. in English) · 2022Article
- Remote Radical Desaturation of Unactivated C-H Bonds in Amides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Copper-catalyzed dehydrogenative γ-C(spNature communications · 2019Article
- Allyl-Nickel Catalysis Enables Carbonyl Dehydrogenation and Oxidative Cycloalkenylation of Ketones.Journal of the American Chemical Society · 2019Article
- Chemoselective α,β-Dehydrogenation of Saturated Amides.Angewandte Chemie (International ed. in English) · 2019Article
- Differentiation between enamines and tautomerizable imines in the oxidation reaction with TEMPO.Nature communications · 2018Article
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
In organic molecules, the reactivity at the carbon atom next to the functional group is dramatically different from that at other carbon atoms. Herein, we report that a versatile copper-catalyzed method enables successive dehydrogenation or dehydrogenation of ketones, aldehydes, alcohols, α,β-unsaturated diesters, and N-heterocycles to furnish stereodefined conjugated dienecarbonyls, polyenecarbonyls, and nitrogen-containing heteroarenes. On the basis of mechanistic studies, the copper-catalyzed successive dehydrogenation process proceeds via the initial α,β-desaturation followed by further dehydrogenative desaturation of the resultant enone intermediate, demonstrating that the reactivity at α-carbon is transferred through carbon-carbon double bond or longer π-system to the carbon atoms at the positions γ, ε, and η to carbonyl groups. The dehydrogenative desaturation-relay is ascribed to the formation of an unusual radical intermediate stabilized by 5- or 7,- or 9-center π-systems. The discovery of successive dehydrogenation may open the door to functionalizations of the positions distant from functional groups in organic molecules.
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Registered trials
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