Synthesis of Aliphatic Azides by Photoinduced C(sp3)–H Azidation

A photoinduced synthesis of aliphatic azides was achieved in a single step starting from the parent cyclic alkanes, as well as from tetrahydrofuran and pyrrolidine derivatives. The reaction proceeds via direct azidation of C(sp³)–H bonds in the presence of 4-benzoylpyridine under photoirradiation conditions utilizing tosyl azide as the azide source. The chemoselective C–H mono-azidation at room temperature and the formation of azide compounds in spite of their potential photolability are the key features of the present transformation.