Copper-Catalyzed 1,2-Diazidation and 1,2-Azidooxygenation of 1,3-Dienes: Three Divergent Protocols Using Zhdankin’s Reagent

A series of three divergent protocols for the copper-catalyzed azidation of 1,3-dienes using iodine(III) Zhdankin's reagent is reported. This strategy features protocols for 1,2-diazidation, two-component 1,2-azidooxygenation, and three-component 1,2-azidooxygenation of 1,3-dienes in highly chemo-, regio-, and site-selective fashion under mild conditions. Excellent to fair yields are reported for a variety of activated and unactivated 1,3-diene systems with a range of substitution patterns. Additionally, mechanistic investigations are included to provide insights into the underpinnings for the divergence of these protocols and the component requirements.