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

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posted on 20.03.2015, 00:00 by Haitao Zhu, Pinhong Chen, Guosheng Liu
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.