ArticleJournal of the American Chemical Society2023
Synthesis of β,γ-Unsaturated Aliphatic Acids via Ligand-Enabled Dehydrogenation.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Catalyst-controlled site-selective dehydrogenation, a stepping stone for C-H oxidations in complex terpenes synthesis.Nature communications · 2026Article
- Transition Metal-Catalyzed Direct C(spChemical reviews · 2026Review
- Biocatalytic site- and stereoselective carbonyl desaturation for late-stage functionalization of cyclic ketones.Nature chemistry · 2026Article
- Synthesis of Spiro Carbocycles via Methyl β-C(spJournal of the American Chemical Society · 2026Article
- From Mono-Accounts of chemical research · 2025Review
- Practical Ligand-Enabled C-H Halogenation of (Hetero)Benzoic and (Hetero)Aryl Acetic Acids.Journal of the American Chemical Society · 2025Article
- Transition-Metal-Catalyzed C(spTopics in current chemistry (Cham) · 2025Review
- Synthesis of Chiral Carbocycles via Enantioselective β,γ-Dehydrogenation.Nature synthesis · 2024Article
- One-Step Synthesis of Chiral 9,10-Dihydrophenanthrenes via Ligand-Enabled Enantioselective Cascade β,γ-Diarylation of Acids.Angewandte Chemie (International ed. in English) · 2024Article
- Tandem dehydrogenation-olefination-decarboxylation of cycloalkyl carboxylic acids via multifold C-H activation.Nature communications · 2024Article
- Ligand-Enabled Double γ-C(spAngewandte Chemie (International ed. in English) · 2023Article
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7 authors.
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Abstract
α,β-Dehydrogenation of aliphatic acids has been realized through both enolate and β-C-H metalation pathways. However, the synthesis of isolated β,γ-unsaturated aliphatic acids via dehydrogenation has not been achieved to date. Herein, we report the ligand-enabled β,γ-dehydrogenation of abundant and inexpensive free aliphatic acids, which provides a new synthetic disconnection as well as a versatile platform for the downstream functionalization of complex molecules at remote γ-sites. A variety of free aliphatic acids, including acyclic and cyclic systems with ring sizes from five-membered to macrocyclic, undergo efficient dehydrogenation. Notably, this protocol features good chemoselectivity in the presence of more accessible α-C-H bonds and excellent regioselectivity in fused bicyclic scaffolds. The utility of this protocol has been demonstrated by the late-stage functionalization of a series of bioactive terpene natural products at the γ-sites. Further functionalization of the β,γ-double bond allows for the installation of covalent warheads, including epoxides, aziridines, and β-lactones, into complex natural product scaffolds, which are valuable for targeted covalent drug discovery.
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