ArticleAngewandte Chemie (International ed. in English)2021
Redox-Neutral Vicinal Difunctionalization of Five-Membered Heteroarenes with Dual Electrophiles.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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9 citing papers in PubMed.
- Functionalization of Heteroarenes via Palladium/Norbornene-Catalyzed Double C-H Activation.Accounts of chemical research · 2026Article
- Photothermal catalysis versus thermal catalysis: A palladium-catalyzed intermolecular three-component C─H 1,3-Science advances · 2026Article
- Structural effects of arsine ligands on C-H difunctionalization of thiophene.Chemical science · 2025Article
- Advances in Vicinal Dicarbo-C-H-functionalization of Five-Membered Heteroarenes via Palladium/Norbornene Cooperative Catalysis.Tetrahedron letters · 2025Article
- Triple cross-electrophile coupling enabled by palladium/norbornene cooperative catalysis.Science advances · 2025Article
- Chiral dinitrogen ligand enabled asymmetric Pd/norbornene cooperative catalysis toward the assembly of C-N axially chiral scaffolds.Nature communications · 2024Article
- Rapid and Modular Access to Multifunctionalized 1,2-Azaborines via Palladium/Norbornene Cooperative Catalysis.Journal of the American Chemical Society · 2024Article
- Palladium/Norbornene-Catalyzed Direct Vicinal Di-Carbo-Functionalization of Indoles: Reaction Development and Mechanistic Study.Angewandte Chemie (International ed. in English) · 2023Article
- S,O-Ligand Promoted meta-C-H Arylation of Anisole Derivatives via Palladium/Norbornene Catalysis.Angewandte Chemie (International ed. in English) · 2022Article
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Abstract
A new reaction mode of palladium/norbornene (Pd/NBE) cooperative catalysis is reported involving the selective coupling of two different carbon-based electrophiles for vicinal double C-H functionalization of five-membered heteroarenes in a site-selective and redox-neutral manner. The key is to use alkynyl bromides as the second electrophile, which allows vicinal difunctionalization of a wide range of heteroarenes including pyrroles, thiophenes and furans at their C4 and C5 positions. One- or two-step tetrafunctionalizations of simple pyrrole and thiophene have also been realized. The C2-substituted NBEs prove most effective in these reactions, and the mechanistic exploration discloses the origin of the high selectivity of this transformation. Synthetic utility of this method has been exemplified in the concise preparations of thiophene-containing organic materials and a protein kinase inhibitor analogue. Preliminary success has also been achieved in a direct annulation event, using a tethered ketone as the second electrophile.
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