ArticleJournal of the American Chemical Society2022
One-Step Synthesis of β-Alkylidene-γ-lactones via Ligand-Enabled β,γ-Dehydrogenation of Aliphatic Acids.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 60 citations in OpenAlex.
- Ligand-Enabled Stereoselective Coupling of Methylene C(spAngewandte Chemie (International ed. in English) · 2026Article
- Formal Diels-Alder reaction of saturated carboxylic acids via C-H activation.Nature chemistry · 2026Article
- Transition Metal-Catalyzed Direct C(spChemical reviews · 2026Review
- Synthesis of Spiro Carbocycles via Methyl β-C(spJournal of the American Chemical Society · 2026Article
- From Mono-Accounts of chemical research · 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
- Palladium-catalysed methylene C(Nature synthesis · 2024Article
- Comprehensive Mechanistic Analysis of Palladium- and Nickel-Catalyzed α,β-Dehydrogenation of Carbonyls via Organozinc Intermediates.The Journal of organic chemistry · 2024Article
- Ligand-Enabled γ-C(spJournal of the American Chemical Society · 2023Article
- Ligand-Enabled Double γ-C(spAngewandte Chemie (International ed. in English) · 2023Article
- Access to unsaturated bicyclic lactones by overriding conventional C(spNature chemistry · 2023Article
- Synthesis of β,γ-Unsaturated Aliphatic Acids via Ligand-Enabled Dehydrogenation.Journal of the American Chemical Society · 2023Article
- Synthesis of 1,3-Dienes via Ligand-Enabled Sequential Dehydrogenation of Aliphatic Acids.Journal of the American Chemical Society · 2023Article
- β- and γ-C(spAngewandte Chemie (International ed. in English) · 2023Article
- Ligand-Enabled Pd(II)-Catalyzed β-Methylene C(spJournal of the American Chemical Society · 2022Article
- Ligand-Enabled C-H Hydroxylation with Aqueous HJournal of the American Chemical Society · 2022Article
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
Abstract
Ligand-enabled Pd-catalyzed regioselective α,β-dehydrogenation of carbonyl compounds via β-methylene C-H activation has recently emerged as a promising transformation. Herein, we report the realization of β,γ-dehydrogenation and subsequent vinyl C-H olefination reactions of free carboxylic acids, thus providing a unique method for the structural diversification of aliphatic acids containing α-quaternary centers through sequential functionalizations of two β-C-H bonds and one γ-C-H bond. This tandem dehydrogenation-olefination-lactonization reaction offers a one-step preparation of β-alkylidene-γ-lactones, which are often difficult to prepare through conventional methods, from inexpensive and abundant free aliphatic acids. A variety of free aliphatic acids, such as isosteviol and grandiflorolic acid natural products, and olefins are compatible with the reported protocol. The newly designed bidentate oxime ether-pyridone and morpholine-pyridone ligands are crucial for this tandem reaction to proceed. Notably, these ligands also enable preferential methylene C-H activation over the previously reported, competing process of methyl C-H bond olefination.
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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.