Palladium-catalyzed intramolecular aminoacetoxylation of unactivated alkenes with hydrogen peroxide as oxidant

Organic Letters
Haitao ZhuGuosheng Liu

Abstract

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.

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Citations

Dec 5, 2015·Journal of the American Chemical Society·Chaohuang ChenGuosheng Liu
Jun 18, 2017·Organic Letters·Jiuzhong HuangHuanfeng Jiang

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