Pd-Catalyzed γ-C(sp³)-H Fluorination of Free Amines.

ABSTRACT: 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-methyl 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 methyl fluorination. The explicit participation of Ag results in a lower energetic span for methylene fluorination and a higher energetic span for methyl fluorination, which is consistent with the experimental observation that the addition of silve

SUBMITTER: Chen YQ 

PROVIDER: S-EPMC7685760 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature