ArticleACS catalysis2023
Transition-State Stabilization by Secondary Orbital Interactions between Fluoroalkyl Ligands and Palladium During Reductive Elimination from Palladium(aryl)(fluoroalkyl) Complexes.
Article in ACS catalysis, 2023. 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.
- Origins of the selectivity of late transition metals of Group 9 and Group 10 for oxidative addition of C-HChemical science · 2026Article
- Versatile Strategy for Organic Surface Modification of Cobalt Phosphide Using Iodonium Salts Enables Systematic Tuning for Hydrogenation Catalysis.Journal of the American Chemical Society · 2026Article
- Woodward and Hoffmann on Secondary Orbital Interactions. How to Make a Fine Two-Course Meal from Leftovers.Chemical record (New York, N.Y.) · 2025Review
- IPr*Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
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Authors and funding
3 authors.
Funding
Abstract
Palladium-catalyzed fluoroalkylations of aryl halides are valuable reactions for the synthesis of fluorinated, biologically active molecules. Reductive elimination from an intermediate Pd(aryl) (fluoroalkyl) complex is the step that forms the C(aryl)-C(fluoroalkyl) bond, and this step typically requires higher temperatures and proceeds with slower rates than the reductive elimination of nonfluorinated alkylarenes from the analogous Pd(aryl) (alkyl) complexes. The experimental rates of this step correlate poorly with common parameters, such as the steric property or the electron-withdrawing ability of the fluoroalkyl ligand, making the prediction of rates and the rational design of Pd-catalyzed fluoroalkylations difficult. Therefore, a systematic study of the features of fluoroalkyl ligands that affect the barrier to this key step, including steric properties, electron-withdrawing properties, and secondary interactions, is necessary for the future development of fluoroalkylation reactions that occur under milder conditions and that tolerate additional types of fluoroalkyl reagents. We report computational studies of the effect of the fluoroalkyl
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