ArticleJournal of the American Chemical Society2018
Diastereodivergent Reductive Cross Coupling of Alkynes through Tandem Catalysis: Z- and E-Selective Hydroarylation of Terminal Alkynes.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 76 citations in OpenAlex.
- Reductive Cross-Coupling of Alkynes with Aryl Bromides via Zr/Pd Synergistic Catalysis.Organic letters · 2026Article
- From alkynes to spiroindole δ-lactamsChemical science · 2026Article
- Facile (Z)-Selective Synthesis of β,γ-Unsaturated Ketones by a Silicon-based Olefination Strategy.Angewandte Chemie (International ed. in English) · 2025Article
- Application of Asymmetric Catalysis in theJournal of the American Chemical Society · 2025Article
- Catalyst-controlled stereodivergent synthesis of polysubstituted alkenes.Nature communications · 2025Article
- The stereo-divergent functionalization of alkynes: a comprehensive review.RSC advances · 2025Review
- Ruthenium-Catalyzed Transfer Hydrogenation of Alkynes: Access to Alkanes and (The Journal of organic chemistry · 2025Article
- Tandem manganese catalysis for the chemo-, regio-, and stereoselective hydroboration of terminal alkynes:RSC advances · 2024Article
- Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.Organic process research & development · 2022Review
- Z-Selective Dienylation Enables Stereodivergent Construction of Dienes and Unravels a Ligand-Driven Mechanistic Dichotomy.ACS catalysis · 2021Article
- Copper-catalyzed functionalization of enynes.Chemical science · 2020Review
- Synthesis of Stereodefined 1,1-Diborylalkenes via Copper-Catalyzed Diboration of Terminal Alkynes.Organic letters · 2020Article
- Generation of Aryl Radicals from Aryl Hydrazines via Catalytic Iodine in Air: Arylation of Substituted 1,4-Naphthoquinones.ACS omega · 2020Article
- A general asymmetric copper-catalysed Sonogashira C(spNature chemistry · 2019Article
- Synthesis of Isomerically Pure (Journal of the American Chemical Society · 2019Article
- Differential Dihydrofunctionalization of Terminal Alkynes: Synthesis of Benzylic Alkyl Boronates through Reductive Three-Component Coupling.Journal of the American Chemical Society · 2019Article
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3 authors at 1 institution in 1 country.
Funding
Abstract
A diastereodivergent hydroarylation of terminal alkynes is accomplished using tandem catalysis. The hydroarylation allows highly selective synthesis of both E and Z diastereoisomers of aryl alkenes, from the same set of starting materials, using the same combination of palladium and copper catalysts. The selectivity is controlled by simple changes in the stoichiometry of the alcohol additive. The hydroarylation has excellent substrate scope and can be accomplished in the presence of various classes of compounds, including esters, nitriles, alkyl halides, epoxides, carbamates, acetals, ethers, silyl ethers, and thioethers. The Z-selective hydroarylation is accomplished using a new approach based on tandem Sonogashira coupling and catalytic semireduction. The E-selective hydroarylation involves an additional catalytic isomerization of the Z-alkene. Our explorations of the reaction mechanism explain the role of individual reaction components and how the subtle changes in the reaction conditions influence the rates of specific steps of the hydroarylation. Our studies also show that, although the Z- and E-selective hydroarylation reactions are mechanistically closely related, the roles of the palladium and copper catalysts in the two reactions are different.
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