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Regiocontrolled Wacker Oxidation of Cinnamyl Azides

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journal contribution
posted on 02.03.2018, 17:33 by Angela S. Carlson, Cristian Calcanas, Ryan M. Brunner, Joseph J. Topczewski
A highly regioselective Wacker oxidation has been developed for the oxidation of cinnamyl azides. The catalytic oxidation tolerates the azide functionality, and more than 15 β-azido ketones were isolated (25–92% yield). High regioselectivity for the aryl ketone is observed in all cases. A robustness screen was conducted to determine functional group tolerance. The products of the oxidaiton can be readily diversified.