ArticleJournal of the American Chemical Society2013
Oxidative Heck vinylation for the synthesis of complex dienes and polyenes.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Synthesis of 1,3-Dienes via Ligand-Enabled Sequential Dehydrogenation of Aliphatic Acids.Journal of the American Chemical Society · 2023Article
- Catalytic Dienylation: An Emergent Strategy for the Stereoselective Construction of Conjugated Dienes and Polyenes.Synthesis · 2023Article
- Iron-Catalyzed Cross-Coupling of α-Allenyl Esters with Grignard Reagents for the Synthesis of 1,3-Dienes.Organic letters · 2023Article
- Z-Selective Dienylation Enables Stereodivergent Construction of Dienes and Unravels a Ligand-Driven Mechanistic Dichotomy.ACS catalysis · 2021Article
- Modern Synthetic Methods for the Stereoselective Construction of 1,3-Dienes.Molecules (Basel, Switzerland) · 2021Review
- Regio- and Diastereoselective Iron-Catalyzed [4+4]-Cycloaddition of 1,3-Dienes.Journal of the American Chemical Society · 2019Article
- Intermolecular Heck Coupling with Hindered Alkenes Directed by Potassium Carboxylates.Angewandte Chemie (International ed. in English) · 2019Article
- Highly Regio- and Stereoselective Catalytic Synthesis of Conjugated Dienes and Polyenes.Journal of the American Chemical Society · 2018Article
- HOTf-Catalyzed Alkyl-Heck-type Reaction.iScience · 2018Article
- Dehydrogenative desaturation-relay via formation of multicenter-stabilized radical intermediates.Nature communications · 2017Article
- Chemo- and regioselective C(sp³)-H arylation of unactivated allylarenes by deprotonative cross-coupling.Angewandte Chemie (International ed. in English) · 2014Article
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3 authors.
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Abstract
We introduce an oxidative Heck reaction for selective complex diene and polyene formation. The reaction proceeds via oxidative Pd(II)/sulfoxide catalysis that retards palladium-hydride isomerizations which previously limited the Heck manifold's capacity for furnishing stereodefined conjugated dienes. Limiting quantities of nonactivated terminal olefins (1 equiv) and slight excesses of vinyl boronic esters (1.5 equiv) that feature diverse functionality can be used to furnish complex dienes and polyenes in good yields and excellent selectivities (generally E:Z = >20:1; internal:terminal = >20:1). Because this reaction only requires prior activation of a single vinylic carbon, improvements in efficiency are observed for synthetic sequences relative to ones featuring reactions that require activation of both coupling partners.
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