Regiocontrolled Wacker Oxidation of Cinnamyl Azides

Org Lett. 2018 Mar 16;20(6):1604-1607. doi: 10.1021/acs.orglett.8b00344. Epub 2018 Mar 2.

Abstract

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides / chemistry*
  • Catalysis
  • Ketones
  • Molecular Structure
  • Oxidation-Reduction

Substances

  • Azides
  • Ketones