ArticleJournal of the American Chemical Society2023
Dual-Ligand Catalyst for the Nondirected C-H Olefination of Heteroarenes.
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 8 papers.
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Who cites it
8 citing papers in PubMed, 53 citations in OpenAlex.
- Palladium(II)-Catalyzed Nondirected C(spJACS Au · 2025Article
- Article
- Dual-Ligand Strategy in Rh-Catalyzed Sequential Hydrofunctionalization of Valylene.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- From Mono-Accounts of chemical research · 2025Review
- Palladium-Catalyzed Non-Directed C─H Functionalization of Arenes with Trifluoromethylated Olefins.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Copper-Catalyzed Cyclization and Alkene Transposition Cascade Enables a Modular Synthesis of Complex Spirocyclic Ethers.Journal of the American Chemical Society · 2025Article
- Ligand-Controlled NondirectedACS catalysis · 2024Article
- Divergent total syntheses of pyrroloiminoquinone alkaloids enabled by the development of a Larock/Buchwald-Hartwig annulation/cyclization.Chemical science · 2024Article
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
Abstract
Pd(II)-catalyzed nondirected C-H functionalization of heteroarenes is a significant challenge for the following reasons: poor reactivity of electron-deficient heterocycles and the unproductive coordination of Lewis basic nitrogen atoms. Existing methodologies using palladium catalysis often employ a large excess of heterocycle substrates to overcome these hurdles. Despite recent advances in nondirected functionalization of arenes that allow them to be used as limiting reagents, the reaction conditions are incompatible with electron-deficient heteroarenes. Herein we report a dual-ligand catalyst that enables Pd(II)-catalyzed nondirected C-H olefination of heteroarenes without using a large excess of substrate. In general, the use of 1-2 equiv of substrates was sufficient to obtain synthetically useful yields. The reactivity was rationalized by the synergy between two types of ligands: a bidentate pyridine-pyridone ligand promotes C-H cleavage; the monodentate heterocycle substrate acts as a second ligand to form a cationic Pd(II) complex that has high affinity for arenes. The proposed dual-ligand cooperation is supported by a combination of X-ray, kinetics, and control experiments.
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Registered trials
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