Copper-Catalyzed Three-Component Carboazidation of Alkenes with Acetonitrile and Sodium Azide

A copper-catalyzed three-component reaction of alkenes, acetonitrile, and sodium azide afforded gamma-azido alkyl nitriles by formation of one C(sp(3))-C(sp(3)) bond and one C(sp(3))-N bond. The transformation allows concomitant introduction of two highly versatile groups (CN and N-3) across the double bond. A sequence involving the copper-mediated generation of a cyanomethyl radical and its subsequent addition to an alkene, and a C(sp(3))-N bond formation accounted for the reaction outcome. The resulting gamma-azido alkyl nitrile can be easily converted into 1,4-diamines, gamma-amino nitriles, gamma-azido esters, and gamma-lactams of significant synthetic value.