Remote, Late-Stage Oxidation of Aliphatic C-H Bonds in Amide-Containing Molecules.

ABSTRACT: Amide-containing molecules are ubiquitous in natural products, pharmaceuticals, and materials science. Due to their intermediate electron-richness, they are not amenable to any of the previously developed N-protection strategies known to enable remote aliphatic C-H oxidations. Using information gleaned from a systematic study of the main features that makes remote oxidations of amides in peptide settings possible, we developed an imidate salt protecting strategy that employs methyl trifluoromethanesulfonate as a reversible alkylating agent. The imidate salt strategy enables, for the first time, remote, nondirected, site-selective C(sp³)-H oxidation with Fe(PDP) and Fe(CF₃PDP) catalysis in the presence of a broad scope of tertiary amides, anilide, 2-pyridone, and carba

SUBMITTER: Nanjo T 

PROVIDER: S-EPMC5812270 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature