A Very Mild and Chemoselective Oxidation of Alcohols to Carbonyl Compounds

Efficient oxidation of primary alcohols and β-amino alcohols to the corresponding aldehydes and α-amino aldehydes can be carried out at room temperature and in methylene chloride, using trichloroisocyanuric acid in the presence of catalytic TEMPO: aliphatic, benzylic, and allylic alcohols, and β-amino alcohols are rapidly oxidized without no overoxidation to carboxylic acids. Secondary carbinols are slowly oxidized so that the reaction is highly chemoselective.