Unexpected Metal-Free Dehydrogenation of a β-Ketoester to a Phenol Using a Recyclable Oxoammonium Salt

The conversion of ethyl 2-oxocyclohexanecarboxylate to ethyl salicylate using an oxoammonium salt is reported. The dehydrogenation reaction is operationally simple and compares favorably with previous literature examples for the same transformation and expands the scope of oxoammonium salts as reagents for oxidative functionalization processes.

Tandem Elimination-Oxidation of Tertiary Benzylic Alcohols with an Oxoammonium Salt

Tertiary benzylic alcohols react with oxoammonium salts, undergoing a tandem elimination / allylic oxidation to provide an allylic ether product in a single step. This mode of reactivity provides a...

Selective cleavage and reconstruction of C–N/C–C bonds in saturated cyclic amines: tunable synthesis of lactams and functionalized acyclic amines

Selective cleavage and functionalization of C–N/C–C bonds in saturated cyclic amines under the promotion of oxoammonium salt and tert-butyl hydroperoxide in the presence of different additives have been developed. To...

Bioinspired Cyclization of in Situ Generated γ-Indolyl β,γ-Unsaturated α-Keto Esters via Oxidative Enamine Process: Facile Approaches to Pyrano[2,3-b]indoles

A bioinspired cyclization of in situ generated -indolyl ,-unsaturated -ketoester with an oxoammonium salt via oxidative enamine process has been developed. Under mild conditions, the reactions afforded pyrano[2,3-b]indoles, which feature...

Metal Free Amino-Oxidation of Electron Rich Alkenes Mediated by an Oxoammonium Salt

<div> <div> <div> <p>4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate (Bobbitt’s salt) effectively activates electron rich alkenes and promotes the addition of anilines. This transformation provides a direct, transition metal free method for amino-oxidation of alkenes under mild conditions. The relative stereochemistry of the amino-oxidation is influenced by solvent effects, with both the syn and anti amino-oxidation products being accessible from identical starting materials. </p> </div> </div> </div>

Metal Free Amino-Oxidation of Electron Rich Alkenes Mediated by an Oxoammonium Salt

<div> <div> <div> <p>4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate (Bobbitt’s salt) effectively activates electron rich alkenes and promotes the addition of anilines. This transformation provides a direct, transition metal free method for amino-oxidation of alkenes under mild conditions. The relative stereochemistry of the amino-oxidation is influenced by solvent effects, with both the syn and anti amino-oxidation products being accessible from identical starting materials. </p> </div> </div> </div>