Attractive aerobic access to the α,β-unsaturated acyl azolium intermediate: oxidative NHC catalysis via multistep electron transfer

Abstract

To replace high molecular weight oxidants with air (O₂) we introduce multistep electron transfer NHC catalysis. The method provides a general and selective oxidation of the α,β-unsaturated aldehyde derived homoenolate to the synthetically useful α,β-unsaturated acyl azolium intermediate. Several independent oxidative NHC-catalyzed reactions are viable with this strategy and the products can be isolated in high to excellent yields.