Oxone-Mediated Mild Removal of an Azine Protecting/Directing Group for Applications in Organic Synthesis

Abstract Azine derivatives of carbonyl compounds are used as protecting groups and have recently been utilized as directing groups in C–H activation. The stability of the azine functional group limits its application in areas where its subsequent removal is desirable. We herein report a mild and efficient method for removal of an azine group using Oxone as a green oxidant in the presence of an acetone/water solvent system. Carbonyl regeneration occurs in high yields from a range of aldazine and ketazine derivatives. A gram-scale synthesis and removal of the azine directing group from an ortho-functionalized azine are performed to extend the application of this methodology.