ArticleAngewandte Chemie (International ed. in English)2020
Integrating Allyl Electrophiles into Nickel-Catalyzed Conjunctive Cross-Coupling.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Article
- Nickel-Catalyzed Branched Hydroalkylation of Alkenes with Diazo Compounds.Journal of the American Chemical Society · 2025Article
- Ligand-enabled Ni-catalysed dicarbofunctionalisation of alkenes with diverse native functional groups.Nature communications · 2024Article
- Three-component dicarbofunctionalization of allylaminesChemical science · 2024Article
- Ni-Catalyzed Regio- and Stereoselective Alkylarylation of Unactivated Alkenes in γ,δ-Alkenylketimines.ACS catalysis · 2022Article
- Directed, nickel-catalyzed 1,2-alkylsulfenylation of alkenyl carbonyl compounds.Chemical science · 2022Article
- Directed Markovnikov hydroarylation and hydroalkenylation of alkenes under nickel catalysis.Chemical science · 2021Article
- Photoinduced 1,2-dicarbofunctionalization of alkenes with organotrifluoroborate nucleophilesChemical science · 2021Article
- Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes.Chemical science · 2021Article
- Mechanism-Based Design of an Amide-Directed Ni-Catalyzed Arylboration of Cyclopentene Derivatives.Organic letters · 2021Article
- Ni-Catalyzed Regioselective 1,2-Dialkylation of Alkenes Enabled by the Formation of Two C(spJournal of the American Chemical Society · 2020Article
- Nickel-Catalyzed Dicarbofunctionalization of Alkenes.ACS catalysis · 2020Article
- Recent developments in nickel-catalyzed intermolecular dicarbofunctionalization of alkenes.Chemical science · 2020Review
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6 authors.
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Abstract
Allylation and conjunctive cross-coupling represent two useful, yet largely distinct, reactivity paradigms in catalysis. The union of these two processes would offer exciting possibilities in organic synthesis but remains largely unknown. Herein, we report the use of allyl electrophiles in nickel-catalyzed conjunctive cross-coupling with a non-conjugated alkene and dimethylzinc. The transformation is enabled by weakly coordinating, monodentate aza-heterocycle directing groups that are useful building blocks in synthesis, including saccharin, pyridones, pyrazoles, and triazoles. The reaction occurs under mild conditions and is compatible with a wide range of allyl electrophiles. High chemoselectivity through substrate directivity is demonstrated by the facile reactivity of the β-γ alkene of the starting material, whereas the ϵ-ζ alkene of the product is preserved. The generality of this approach is further illustrated through the development of an analogous method with alkyne substrates. Mechanistic studies reveal the importance of the dissociation of the weakly coordinating directing group to allow the allyl moiety to bind and facilitate C(sp
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