Radical oxyamination of vinyl azides with N-hydroxyphthalimide under the action of [bis(trifluoroacetoxy)iodo]benzene

O,O'-Bis(phthalimido)-modified 2-(hydroxyimino)ethanols containing N-O-N fragment were synthesized in high yields via the reaction of vinyl azides with N-hydroxyphthalimide under the action of hypervalent iodine-based oxidant. The reaction proceeds under mild conditions and is compatible with a wide range of vinyl azides. Presumably, the process starts with the oxidative formation of phthalimide-N-oxyl radical, followed by its addition to vinyl azide with the subsequent trapping of the generated iminyl radical with the second phthalimide-N-oxyl radical.

Automated summary

O,O'-Bis(phthalimido)-modified 2-(hydroxyimino)ethanols containing N-O-N fragment were synthesized efficiently by reacting vinyl azides with N-hydroxyphthalimide under the influence of a hypervalent iodine-based oxidant. The reaction proceeds under mild conditions and is compatible with a wide range of vinyl azides.