Oxidation of benzylic alcohols to carbonyls using N-heterocyclic stabilized λ3-iodanes

Abstract

We present N-heterocycle-stabilized iodanes (NHIs) as suitable reagents for the mild oxidation of activated alcohols. Two different protocols, both involving activation by chloride additives, were used to synthesize benzylic ketones and aldehydes without overoxidation in up to 97% yield. Based on MS experiments an activated hydroxy(chloro)iodane is proposed as the reactive intermediate.

Keywords

• alcohol oxidation
• hypervalent iodine
• n-heterocycles