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

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) & sdot; 2H(2)O 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) & sdot; 2H(2)O. The well-known ability of this reagent to act through single-electron transfer (SET) makes plausible a radical mechanism involving high valent palladium complexes.