ArticleJournal of the American Chemical Society2020
Ni-Catalyzed Regioselective 1,2-Dialkylation of Alkenes Enabled by the Formation of Two C(sp
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed.
- Stereoselective vicinal C(sp³)-C bond formation via metallaphotoredox 1,2-difunctionalization of internal alkenes.Nature communications · 2026Article
- Catalytic Reductive Annulation Reactions of Alkenes Using Dihaloalkanes.Tetrahedron letters · 2025Article
- Alkene Carboxy-Alkylation via COJournal of the American Chemical Society · 2024Article
- Iron-Mediated Dialkylation of Alkenylarenes with Benzyl Bromides.The Journal of organic chemistry · 2024Article
- Interception and Synthetic Application of Diradical and Diene Forms of Dual-Nature Azabicyclic o-Quinodimethanes Generated by 6π-Azaelectrocyclization.Angewandte Chemie (International ed. in English) · 2024Article
- Fe-Catalyzed Fluoroalkyl(hetero)arylation of Vinyl Azaarenes: Rapid and Modular Synthesis of Unsymmetrical 1,1-Bis(hetero)arylalkanes.Organic letters · 2024Article
- Harnessing Bromo/Acyloxy Transposition (BrAcT) and Excited-State Copper Catalysis for Styrene Difunctionalization.Journal of the American Chemical Society · 2024Article
- Triple Radical Sorting: Aryl-Alkylation of Alkenes.Journal of the American Chemical Society · 2024Article
- Alkene dialkylation by triple radical sorting.Nature · 2024Article
- A free-radical design featuring an intramolecular migration for a synthetically versatile alkyl-(hetero)arylation of simple olefins.Chemical science · 2024Article
- Congested C(sp3)-rich architectures enabled by iron-catalysed conjunctive alkylation.Nature catalysis · 2024Article
- Iron-catalyzed fluoroalkylative alkylsulfonylation of alkenes via radical-anion relay.Nature communications · 2024Article
- Three-Component Cross-Electrophile Coupling: Regioselective Electrochemical Dialkylation of Alkenes.Journal of the American Chemical Society · 2023Article
- Salt-stabilized alkylzinc pivalates: versatile reagents for cobalt-catalyzed selective 1,2-dialkylation.Chemical science · 2023Article
- Nickel-Catalyzed Regioselective Intermolecular Dialkylation of Alkenylarenes: Generation of Two Vicinal C(spAngewandte Chemie (International ed. in English) · 2023Article
- Dual Nickel/Photoredox-Catalyzed Asymmetric Carbosulfonylation of Alkenes.Journal of the American Chemical Society · 2023Article
- Article
- Nickel-Catalyzed Enantioselective Reductive Alkyl-Carbamoylation of Internal Alkenes.Angewandte Chemie (International ed. in English) · 2022Article
- Ni-Catalyzed Regio- and Stereoselective Alkylarylation of Unactivated Alkenes in γ,δ-Alkenylketimines.ACS catalysis · 2022Article
- Rapid access toChemical science · 2022Article
Corrections and comments
- Erratum issued
Authors and funding
5 authors.
Funding
Abstract
We disclose a Ni-catalyzed vicinal difunctionalization of alkenes with benzyl halides and alkylzinc reagents, which produces products with two new alkyl-alkyl bonds. This alkene dialkylation is effective in combining secondary benzyl halides and secondary alkylzinc reagents with internal alkenes, which furnishes products with three contiguous all-carbon secondary stereocenters. The products can be readily elaborated to access complex tetralene, benzosuberene, and bicyclodecene cores. The reaction also features as the most efficient alkene difunctionalization process to date with catalyst loadings down to 500 ppm and the catalytic turnover number (TON) and turnover frequency (TOF) registering up to 2 × 10
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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.