MIA-Directed 2-Pyridione-Enabled Selective <i>Ortho</i>-C–H Arylation of Phenylalanine: A Mechanistic Study
Pengpeng Niu, Peng‐Yu Liu, Yue‐Ning Meng, Fang Yu, Yu‐Peng He
Abstract
The 2-methoxyiminoacyl-mediated arylation of substituted phenylalanines has been examined. Selective monoarylation at the ortho position was achieved using pyridone ligands which decelerate the arylation process. Density functional theory (DFT) study of a continuous C–H arylation process that included the first and second arylation stage was performed. The computational result shows that the introduction of a pyridone ligand obviously disfavors the second arylation stage, which directly contributes to the selectivity between the mono/diarylated products. Furthermore, results of the kinetic isotope effect and a control experiment are agreed with DFT study.
Topics & Concepts
ChemistryKinetic isotope effectSelectivityDensity functional theoryPhenylalanineLigand (biochemistry)Computational chemistryTwo stepStereochemistryCombinatorial chemistryOrganic chemistryCatalysisDeuteriumBiochemistryReceptorAmino acidQuantum mechanicsPhysicsCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCatalytic Cross-Coupling Reactions