ArticleJournal of the American Chemical Society2025
Impact of Induced Fitting and Secondary Noncovalent Interactions on Site-Selective and Enantioselective C-H Functionalization of Arylcyclohexanes.
Article in Journal of the American Chemical Society, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Interpreting terminal selectivity in undirected C(spChemical science · 2026Review
- Synthesis of Aryl and Heteroaryl Diazophosphonates via Palladium-Catalyzed Cross-Coupling and Their Application in Rhodium-Catalyzed Cyclopropanation.The Journal of organic chemistry · 2026Article
- Desymmetrization of Malonic Monoesters and Malonic Acids via Enantioselective Catalytic C(spAngewandte Chemie (International ed. in English) · 2026Article
- Enantioselective Synthesis of Axially Chiral Spiro[3.3]heptanes by Site-Selective C-H Functionalization.ACS catalysis · 2026Article
- Asymmetric C-H Functionalization of Bicyclo[2.1.1]hexanes and Their 2-Oxa- and 2-Aza Derivatives via Rhodium Carbene Intermediates.Journal of the American Chemical Society · 2026Article
- Enantioselective and Diastereoselective Synthesis of Azaspiro[n.2]alkanes by Rhodium-Catalyzed Cyclopropanations.ACS catalysis · 2025Article
- Rh-Catalyzed Atroposelective Single-Carbon Insertion.Journal of the American Chemical Society · 2025Article
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Authors and funding
7 authors.
Funding
Abstract
A major challenge in organic synthesis is the selective functionalization of C-H bonds. As most organic compounds contain multiple C-H bonds with similar properties, distinguishing between them requires precise control. In this study, we show how transition metal catalysts can adopt many of the characteristics associated with enzymes, leading to unprecedented site-selectivity in the C-H functionalization step. The catalysts are dirhodium complexes that adopt a bowl-shaped shape on formation. The flexible microenvironment within the bowl causes an induced fitting to occur as the reagent and substrate approach the catalyst. The key factors controlling the selectivity are noncovalent interactions between the approaching substrate and the catalyst wall, which cause a specific C-H bond in the substrate to be placed close to the metal-bound reagent.
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Registered trials
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