Role of N‑Acyl Amino Acid Ligands in Pd(II)-Catalyzed Remote C–H Activation of Tethered Arenes

A combined experimental/computational study on the amino acid ligand-assisted Pd-catalyzed C–H bond activation reveals a mechanism in which the amino acid acts as both a dianionic bidentate ligand and a proton acceptor. This new model explains the effects of amino acids on reactivity and selectivity...

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Published inJournal of the American Chemical Society Vol. 136; no. 3; pp. 894 - 897
Main Authors Cheng, Gui-Juan, Yang, Yun-Fang, Liu, Peng, Chen, Ping, Sun, Tian-Yu, Li, Gang, Zhang, Xinhao, Houk, K. N, Yu, Jin-Quan, Wu, Yun-Dong
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 22.01.2014
Subjects
amino acids
Amino Acids - chemistry
Carbon - chemistry
Catalysis
chemical bonding
Hydrocarbons, Aromatic - chemistry
Ligands
Models, Molecular
Molecular Conformation
Palladium - chemistry
Protons
Stereoisomerism
Substrate Specificity
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Summary:A combined experimental/computational study on the amino acid ligand-assisted Pd-catalyzed C–H bond activation reveals a mechanism in which the amino acid acts as both a dianionic bidentate ligand and a proton acceptor. This new model explains the effects of amino acids on reactivity and selectivity and unveils the dual roles of amino acids: stabilizing monomeric Pd complexes and serving as the internal base for proton abstraction.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja411683n