A very mild and chemoselective oxidation of alcohols to carbonyl compounds

Org Lett. 2001 Sep 20;3(19):3041-3. doi: 10.1021/ol016501m.

Abstract

Efficient oxidation of primary alcohols and beta-amino alcohols to the corresponding aldehydes and alpha-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 beta-amino alcohols are rapidly oxidized without no overoxidation to carboxylic acids. Secondary carbinols are slowly oxidized so that the reaction is highly chemoselective. Reaction: see text.