Palladium‐Catalyzed/Mn(OAc)3‐Mediated 1,2‐Diazidation and 1,2‐Acetoxy/Hydroxylation of N‐Allyl Sulfonamides

Abstract

Palladium‐catalyzed conditions for diazidation or acetoxy/hydroxylation of N‐allyl sulfonamides by using Pd(OAc)2 as the catalyst combined with Mn(OAc)3·2H2O have been developed. The 1,2‐diazidation reaction of the carbon‐carbon double bond occurs in mild conditions (i.e. NaN3 as azide source in THF at room temperature), whereas the 1,2‐acetoxy/hydroxylation requires an excess of Mn(OAc)3·2H2O. The well‐known ability of this reagent to act through single‐electron transfer (SET) makes plausible a radical mechanism involving high valent palladium complexes.