Year: 2013
Type: article
Abstract: All articles of this category Introduction Oxoammonium salts have recently attracted much attention as environmentally friendly, shelf-stable alternatives to traditional oxidants.[ 1 ] In addition to being more sustainable, these salts have several advantages: 1) the spent oxidant is easily recovered and recyclable; 2) oxidations are performed under mild conditions and are simple to conduct; 3) oxidations are typically colorimetric processes and reaction progress can be monitored visually.[ 2 ] Scheme 1 Preparation of oxoammonium salts Much of the work involving oxoammonium salts focusses on the conversion of alcohols into the corresponding carbonyl species.[ 3 ] [ 4 ] [ 5 ] [ 6 ] A range of functional groups can be accessed using this strategy including aldehydes,[ 2 ] carboxylic acids,[ 3 ] ketones (including the electron-deficient CF 3 ketone)[ 6 ] and even esters.[ 5 ] While highly effective for this type of transformation, several new applications for oxoammonium salts have been recently explored.[ 8 ] [ 9 ] [ 10 ] [ 11 ] These include several mechanistically interesting transformations such as exhaustive oxidation to give ene-triketones,[ 7 ] tandem dehydrogenative Povarov/oxidation reactions,[ 8 ] tandem α-alkylation/cyclization, α- and γ-alkylation of aldehydes,[ 9 ] and dehydrogenative coupling of benzylic nitrogen/oxygen compounds with enolizable carbonyl groups.[ 10 ]
Source: Synlett
Author: Christopher Kelly
Institution: University of Connecticut
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W2010488040