ArticleNature communications2016
Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism.
Article in Nature communications, 2016. 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.
- Two (methyl-sulfan-yl)benzyl-derivatized palladium-N-heterocyclic carbene complexes - same formula type but not isotypic.Acta crystallographica. Section E, Crystallographic communications · 2026Article
- Comprehensive Mechanistic Analysis of Palladium- and Nickel-Catalyzed α,β-Dehydrogenation of Carbonyls via Organozinc Intermediates.The Journal of organic chemistry · 2024Article
- Tandem Dearomatization/Enantioselective Allylic Alkylation of Pyridines.Journal of the American Chemical Society · 2023Article
- Designed Iron Catalysts for Allylic C-H Functionalization of Propylene and Simple Olefins.Angewandte Chemie (International ed. in English) · 2023Article
- Ir-Catalyzed Asymmetric Allylic Alkylation of Dialkyl Malonates Enabling the Construction of Enantioenriched All-Carbon Quaternary Centers.Journal of the American Chemical Society · 2022Article
- Highly regioselective and diastereodivergent aminomethylative annulation of dienyl alcohols enabled by a hydrogen-bonding assisting effect.Chemical science · 2022Article
- Ligand-controlled regioselective and chemodivergent defluorinative functionalization ofChemical science · 2021Article
- Regio- and enantioselective umpolung gem-difluoroallylation of hydrazones via palladium catalysis enabled by N-heterocyclic carbene ligand.Nature communications · 2021Article
- Enantioselective Intramolecular Allylic Substitution via Synergistic Palladium/Chiral Phosphoric Acid Catalysis: Insight into Stereoinduction through Statistical Modeling.Angewandte Chemie (International ed. in English) · 2020Article
- Catalytic three-component C-C bond forming dearomatization of bromoarenes with malonates and diazo compounds.Chemical science · 2020Article
- Allenoate Prenucleophiles: A Triply Diastereoselective Approach to β-Hydroxy Esters Containing All-Carbon α-Quaternary Centers.Organic letters · 2019Article
- Photocatalytic enantioselective α-aminoalkylation of acyclic imine derivatives by a chiral copper catalyst.Nature communications · 2019Article
- Direct Asymmetric Alkylation of Ketones: Still Unconquered.Angewandte Chemie (International ed. in English) · 2017Review
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Authors and funding
9 authors.
Funding
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Abstract
The palladium-catalysed allylic substitution reaction is one of the most important reactions in transition-metal catalysis and has been well-studied in the past decades. Most of the reactions proceed through an outer-sphere mechanism, affording linear products when monosubstituted allyl reagents are used. Here, we report an efficient Palladium-catalysed protocol for reactions of β-substituted ketones with monosubstituted allyl substrates, simply by using N-heterocyclic carbene as ligand, leading to branched products with up to three contiguous stereocentres in a (syn, anti)-mode with excellent regio and diastereoselectivities. The scope of the protocol in organic synthesis has been examined preliminarily. Mechanistic studies by both experiments and density functional theory (DFT) calculations reveal that the reaction proceeds via an inner-sphere mechanism-nucleophilic attack of enolate oxygen on Palladium followed by C-C bond-forming [3,3']-reductive elimination.
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