Selective Cleavage of Inert Aryl C–N Bonds in N-Aryl Amides

Abstract

A highly selective, IBX-promoted reaction has been developed for the oxidative cleavage of inert C(aryl)-N bonds on secondary amides while leaving the C(carbonyl)-N bond unchanged. This metal-free reaction proceeds under mild conditions (HFIP/HO, 25 °C), providing facile access to various useful primary amides, some of which would be otherwise unattainable using conventional aminolysis and hydrolysis approaches.

Cobaloxime‐Catalyzed Hydrogen Evolution in Photoredox‐Facilitated Small‐Molecule Functionalization

“…In 2018, both Xie and Zhou, [53] as well as Chiang and Lei, [54] reported the synthesis of lactones through a C-O bond formation in an intramolecular CDC (Scheme 25). Both make use of acridinium photosensitizers to oxidize carboxylate moieties, a process analogous to the aforementioned decarboxylative olefinations (Scheme 5).…”

N-Acyl-5,5-dimethylhydantoin, a New Mild Acyl-Transfer Reagent in Pd Catalysis: Highly Efficient Synthesis of Functionalized Ketones

“…In recent years, researchers focused on the construction of carbon–carbon bonds by selective cleavage of the amide C–N bonds. − Much achievement in the field of amides activation and cleavage has been described by the Zou, Garg, Szostak, − Yamaguchi, Shi, and Huang groups . These reactions were catalyzed by a transition metal from various activated amides with conveniently available coupling partners (Figure ).…”

Selective Removal of Aminoquinoline Auxiliary by IBX Oxidation

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