Unexpected Reduction of N-Hydroxyphthalimides to Phthalimides-Orthogonal Reduction of Functionalized N-Hydroxyphthalimides

摘要

A chemoselective reduction of N-hydroxyphthalimides to phthalimides under mild conditions has been discovered. It in-volves reaction of an N-hydroxyimide with bis(pinacolato)diboron in the presence of a base. Other easily reducible functional groups, such as iodo, nitro, or azido groups are unaffected. Alternatively, such functional groups may be selectively reduced without affect-ing the N-hydroxyimide moiety using a set of classical conditions.