ArticleNature communications2021
Catalytic enantioselective reductive domino alkyl arylation of acrylates via nickel/photoredox catalysis.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Synthesis of 2,3-(Diheterocyclyl)Propanoic Acid Esters as New Building Blocks via Complementary Meldrum's Acid and Aza-Michael Strategies.Molecules (Basel, Switzerland) · 2026Article
- Photocatalytic multicomponent alkene dicarbofunctionalizationChemical science · 2026Article
- Stereoselective vicinal C(sp³)-C bond formation via metallaphotoredox 1,2-difunctionalization of internal alkenes.Nature communications · 2026Article
- Ni-catalyzed enantioselective synthesis of β-aminoboronates via spin-center shift and proton transfer.Science advances · 2025Article
- Vinyl cyclopropanes as a unifying platform for enantioselective remote difunctionalization of alkenes.Nature communications · 2025Article
- Triple cross-electrophile coupling enabled by palladium/norbornene cooperative catalysis.Science advances · 2025Article
- Photoredox/Cr-catalyzed enantioselective radical-polar crossover transformation via C-H functionalization.Nature communications · 2025Article
- Enantioselective reductive cross-couplings to forge C(spNature communications · 2025Article
- Asymmetric paired oxidative and reductive catalysis enables enantioselective alkylarylation of olefins with C(spNature communications · 2024Article
- Nickel-catalysed enantioselective alkene dicarbofunctionalization enabled by photochemical aliphatic C-H bond activation.Nature catalysis · 2024Article
- Nickel/photoredox dual catalyzed arylalkylation of nonactivated alkenes.Nature communications · 2023Article
- Dual Nickel/Photoredox-Catalyzed Asymmetric Carbosulfonylation of Alkenes.Journal of the American Chemical Society · 2023Article
- Rapid Synthesis of β-Chiral Sulfones by Ni-Organophotocatalyzed Enantioselective Sulfonylalkenylation of Alkenes.JACS Au · 2023Article
- Nickel-Catalyzed Enantioselective Electrochemical Reductive Cross-Coupling of Aryl Aziridines with Alkenyl Bromides.Journal of the American Chemical Society · 2023Article
- Three-component reductive conjugate addition/aldol tandem reaction enabled by nickel/photoredox dual catalysis.Chemical science · 2023Article
- Article
- Synthesis of Vicinal Carbocycles by Intramolecular Nickel-Catalyzed Conjunctive Cross-Electrophile Coupling Reaction.Organic letters · 2022Article
Corrections and comments
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Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Nonsteroidal anti-inflammatory drug derivatives (NSAIDs) are an important class of medications. Here we show a visible-light-promoted photoredox/nickel catalyzed approach to construct enantioenriched NSAIDs via a three-component alkyl arylation of acrylates. This reductive cross-electrophile coupling avoids preformed organometallic reagents and replaces stoichiometric metal reductants by an organic reductant (Hantzsch ester). A broad range of functional groups are well-tolerated under mild conditions with high enantioselectivities (up to 93% ee) and good yields (up to 90%). A study of the reaction mechanism, as well as literature precedence, enabled a working reaction mechanism to be presented. Key steps include a reduction of the alkyl bromide to the radical, Giese addition of the alkyl radical to the acrylate and capture of the α-carbonyl radical by the enantioenriched nickel catalyst. Reductive elimination from the proposed Ni(III) intermediate generates the product and forms Ni(I).
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