We recently reported two unexplored reactivities of alkynes and azides. The first method reacts nucleophilic alkynes and electrophilic azides to synthesize sulfonyl-substituted 1,5-disubstituted-1,2,3-triazoles. The second method reacts electrophilic alkynes with nucleophilic azides to form alkynyl-azides that immediately extrude dinitrogen to form cyanocarbenes which were trapped by O-H insertion, sulfoxide complexation, and cyclopropanation. The design and discovery of these reactions, along with key observations, is discussed herein.
