ArticleNature communications2022
Ring walking as a regioselectivity control element in Pd-catalyzed C-N cross-coupling.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed, 26 citations in OpenAlex.
- Selectivity for Exhaustive Cross-Coupling of Dihaloarenes is Affected by the Interplay Between Halide Byproduct, Solvent, and Ligand.Organometallics · 2026Article
- Halide Salts Alleviate TMSOK Inhibition in Suzuki-Miyaura Cross-Couplings.ACS catalysis · 2024Article
- Investigating the Origin of Epimerization Attenuation during Pd-Catalyzed Cross-Coupling Reactions.ACS catalysis · 2024Article
- Phase transfer catalysts shift the pathway to transmetalation in biphasic Suzuki-Miyaura cross-couplings.Nature communications · 2024Article
- One-Step Catalyst-Transfer Macrocyclization: Expanding the Chemical Space of Azaparacyclophanes.Journal of the American Chemical Society · 2024Article
- Nickel-Based Catalysts for the Selective Monoarylation of Dichloropyridines: Ligand Effects and Mechanistic Insights.ACS catalysis · 2024Article
- Mechanistic Origin of Ligand Effects on Exhaustive Functionalization During Pd-Catalyzed Cross-Coupling of Dihaloarenes.ACS catalysis · 2024Article
- Indomuscone-Based Sterically Encumbered Phosphines as Ligands for Palladium-Catalyzed Reactions.The Journal of organic chemistry · 2023Article
- A Method for Converting HPLC Peak Area from Online Reaction Monitoring to Concentration Using Nonlinear Regression.The Journal of organic chemistry · 2023Article
- The Road Less Traveled: Unconventional Site Selectivity in Palladium-Catalyzed Cross-Couplings of DihalogenatedACS catalysis · 2022Article
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6 authors at 2 institutions in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
Ring walking is an important mechanistic phenomenon leveraged in many catalytic C-C bond forming reactions. However, ring walking has been scarcely studied under Buchwald-Hartwig amination conditions despite the importance of such transformations. An in-depth mechanistic study of the Buchwald-Hartwig amination is presented focussing on ligand effects on ring walking behavior. The ability of palladium catalysts to promote or inhibit ring walking is strongly influenced by the chelating nature of the ligand. In stark contrast, the resting state of the catalyst had no impact on ring walking behavior. Furthermore, the complexity of the targeted system enabled the differentiation between catalysts which undergo ring walking versus diffusion-controlled coupling. The insights gained in this study were leveraged to achieve desymmetrization of a tetrabrominated precursor. A small library of asymmetric 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'spirobifluorene (SpiroOMeTAD) derivatives were successfully synthesized using this strategy highlighting the ease with which libraries of these compounds can be accessed for screening.
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