A new, convenient, highly selective free-radical hydroxymethylation of heteroaromatic bases by persulfate oxidation of ethylene glycol and glycerol, catalysed by AgNO3

A new, convenient and selective source of hydroxymethyl ( .CH2OH) radical has been developed by persulfate oxidation of ethylene glycol with AgNO3 catalysis. The .CH 2OH radical is selectively trapped by protonated heteroaromatic bases, providing a new, general process of hydroxymethylation; the importance of the β-scission of the alkoxyl radical intermediate is emphasised.