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.
Bibliographical noteFunding Information:
Financial support was provided by the University of Minnesota and The American Chemical Society’s Petroleum Research Fund (PRF No. 56505-DNI1). This research was supported by the National Institute of General Medical Sciences of the National Institutes of Health under Award No. R35GM124718. We also acknowledge NIH Shared Instrumentation Grant No. S10OD011952.
© 2018 American Chemical Society.