MIA-Directed 2‑Pyridione-Enabled Selective Ortho-C–H Arylation of Phenylalanine: A Mechanistic Study

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 includ...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 86; no. 3; pp. 3096 - 3106
Main Authors Niu, Peng-Peng, Liu, Peng-Yu, Meng, Yue-Ning, Yu, Fang, He, Yu-Peng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.02.2021
Amer Chemical Soc
Subjects
arylation
Chemistry
Chemistry, Organic
density functional theory
isotopes
ligands
organic chemistry
phenylalanine
Physical Sciences
pyridones
Science & Technology
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Summary: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.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.0c02872