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

Abstract

AbstractPalladium‐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.