Photo-driven haloazidation cyclization of 1,5-enynes having cyano groups with TMSN3and NIS/NCS/NBS under metal-free conditions

, and N-iodo(bromo, chloro)succinimide under metal-free and oxidant-free conditions was developed. The reaction underwent a radical addition/5-exo-dig cyclization/radical coupling process with the successive formation of C-N, C-C, and C-halogen (Cl, Br, and I) bonds, which was initiated by the addition of an azidyl radical to the carbon-carbon double bond of the 1,5-enyne.