Palladium-Catalyzed Intramolecular Aminoacetoxylation of Unactivated Alkenes with Hydrogen Peroxide as Oxidant

A palladium-catalyzed intramolecular
aminoacetoxylation of unactivated
alkenes was developed in which H2O2 was used
as the sole oxidant. A variety of 3-acetoxylated piperidines were
obtained in good yields with good to excellent regio- and diastereoselectivities.
Mechanistic study revealed that the addition of di­(2-pyridyl) ketone
(dpk) ligand was crucial to promote the oxidative cleavage of the
C–Pd­(II) bond by H2O2 to give the C–OAc
bond.