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

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

Takeshi Nanjo, Emilio C de Lucca Jr, M Christina White

J Am Chem Soc. 2017 Oct 18;139(41):14586-14591.

PMID: 28921954

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 carbamate functionality. Secondary and primary amides can be masked as N-Ns amides to undergo remote oxidation. This novel imidate strategy facilitates late-stage oxidations in a broader scope of medicinally important molecules and may find use in other C-H oxidations and metal-mediated reactions that do not tolerate amide functionality.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP333277	Methyl trifluoromethanesulfonate		333-27-7	Price

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