Regioselective Hydroxysulfenylation of α,β‐Unsaturated Imines: Enhanced Stability of an Intermediate Radical

That's radical! A radical hydroxysulfenylation reaction of α,β-unsaturated imines to give β-hydroxysulfides with high regioselectivity has been developed (see scheme). The introduction of the imino group enhances the stability of the intermediate radical and reduces the ability of organoboranes to act as radical trapping reagents. Bn=benzyl.