ArticleAdvanced science (Weinheim, Baden-Wurttemberg, Germany)2024
Palladium-Catalyzed Atroposelective Suzuki-Miyaura Coupling to Construct Axially Chiral Tetra-Substituted α-Boryl Styrenes.
Article in Advanced science (Weinheim, Baden-Wurttemberg, Germany), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Enantioselective Synthesis of Atropisomeric 1,3-Dienes via Platinum-Catalyzed Hydrosilylation of 1,3-Enynes.Angewandte Chemie (International ed. in English) · 2026Article
- Copper-catalyzed enantioselective interrupted azide-alkyne cycloaddition to access axially chiral diaryl ethers.Chemical science · 2026Article
- Single-carbon-atom transfer toChemical science · 2025Article
- Palladium-Catalyzed Atroposelective Suzuki-Miyaura Coupling to Construct Axially Chiral Tetra-Substituted α-Boryl Styrenes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
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7 authors.
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Abstract
Palladium-catalyzed Suzuki-Miyaura (SM) coupling is a valuable method for forming C─C bonds, including those between aryl moieties. However, achieving atroposelective synthesis of axially chiral styrenes via SM coupling remains challenging. In this study, a palladium-catalyzed atroposelective Suzuki-Miyaura coupling between gem-diborylalkenes and aryl halides is presented. Using the monophosphine ligand Me-BI-DIME (L2), a range of axially chiral tetra-substituted acyclic styrenes with high yields and excellent enantioselectivities are successfully synthesized. Control experiments reveal that the gem-diboryl group significantly influences the product enantioselectivities and the coupling prefers to occur at sites with lower steric hindrance. Additionally, the alkenyl boronate group in the products proves versatile, allowing for various transformations while maintaining high optical purities.
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