ArticleACS catalysis2023
Ligand-Metal Cooperation Enables Net Ring-Opening C-C Activation / Difunctionalization of Cyclopropyl Ketones.
Article in ACS catalysis, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Ligand-modulated metal-radical polarity match enables general 1,2-dicarbofunctionalization of ethylene.Nature chemistry · 2026Article
- Decoupling Cyanide Activation from C-C Bond Formation in Ni-Catalyzed Cyanation of Strained Ketones Using Benzonitriles.Journal of the American Chemical Society · 2026Article
- Review
- Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Triflates with Alkyl Halides: Mechanism-Informed Design of More General Conditions.Journal of the American Chemical Society · 2025Article
- Selective Ni-Catalyzed Cross-Electrophile Coupling of Heteroaryl Chlorides and Aryl Bromides at 1:1 Substrate Ratio.Journal of the American Chemical Society · 2025Article
- Non-Innocent Role of Sacrificial Anodes in Electrochemical Nickel-Catalyzed C(spJournal of the American Chemical Society · 2024Article
- A decarbonylative approach to alkylnickel intermediates and C(spScience (New York, N.Y.) · 2024Article
- Nickel-catalyzed γ-alkylation of cyclopropyl ketones with unactivated primary alkyl chlorides: balancing reactivity and selectivityRSC advances · 2024Article
- Metal-ligand cooperativity in chemical electrosynthesis.Chem catalysis · 2024Article
- Nickel-Catalyzed Defluorinative Coupling of Aliphatic Aldehydes with Trifluoromethyl Alkenes.ACS catalysis · 2022Article
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Authors and funding
6 authors.
Funding
Abstract
Reactions that cleave C-C bonds and enable functionalization at both carbon sites are powerful strategic tools in synthetic chemistry. Stereodefined cyclopropyl ketones have become readily available and would be an ideal source of 3-carbon fragments, but general approaches to net C-C activation / difunctionalization are unknown. Herein we demonstrate the cross-coupling of cyclopropyl ketones with organozinc reagents and chlorotrimethylsilane to form 1,3-difunctionalized, ring-opened products. A combination of experimental and theoretical studies rule out more established mechanisms and shed light on how cooperation between the redox-active terpyridine (tpy) ligand and the nickel atom enables the C-C bond activation step. The reduced (tpy
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