Mangana(iii/iv)electro-catalyzed C(sp3)-H azidation

Manganaelectro-catalyzed azidation of otherwise inert C(sp(3))-H bonds was accomplished using most user-friendly sodium azide as the nitrogen-source. The operationally simple, resource-economic C-H azidation strategy was characterized by mild reaction conditions, no directing group, traceless electrons as the sole redox-reagent, Earth-abundant manganese as the catalyst, high functional-group compatibility and high chemoselectivity, setting the stage for late-stage azidation of bioactive compounds. Detailed mechanistic studies by experiment, spectrophotometry and cyclic voltammetry provided strong support for metal-catalyzed aliphatic radical formation, along with subsequent azidyl radical transfer within a manganese(iii/iv) manifold.

Automated summary

The electro-catalyzed azidation of inert C(sp(3))-H bonds used sodium azide as the nitrogen source, with mild reaction conditions and no directing group. The mechanism involved aliphatic radical formation and azidyl radical transfer within a manganese(iii/iv) manifold.