Reference of cis-4-Aminocyclohexane carboxylic acid. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: cis-4-Aminocyclohexane carboxylic acid, is researched, Molecular C7H13NO2, CAS is 3685-23-2, about Pd-Catalyzed γ-C(sp3)-H Fluorination of Free Amines. Author is Chen, Yan-Qiao; Singh, Sukriti; Wu, Yongwei; Wang, Zhen; Hao, Wei; Verma, Pritha; Qiao, Jennifer X.; Sunoj, Raghavan B.; Yu, Jin-Quan.
The first example of free amine γ-C(sp3)-H fluorination is realized using 2-hydroxynicotinaldehyde as the transient directing group. A wide range of cyclohexyl and linear aliphatic amines could be fluorinated selectively at the γ-Me and methylene positions. Electron withdrawing 3,5-disubstituted pyridone ligands were identified to facilitate this reaction. Computational studies suggest that the turnover determining step is likely the oxidative addition step for methylene fluorination, while it is likely the C-H activation step for Me fluorination. The explicit participation of Ag results in a lower energetic span for methylene fluorination and a higher energetic span for Me fluorination, which is consistent with the exptl. observation that the addition of silver salt is desirable for methylene but not for Me fluorination. Kinetic studies on Me fluorination suggest that the substrate and PdL are involved in the rate-determining step, indicating that the C-H activation step may be partially rate-determining Importantly, an energetically preferred pathway has identified an interesting pyridone-assisted bimetallic transition state for the oxidative addition step in methylene fluorination, thus uncovering a potential new role of the pyridone ligand.
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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate