Chan–Lam Reaction and Lewis Acid Promoted 1,3-Rearrangement of N–O Bonds to Prepare <i>N</i>-(2-Hydroxyaryl)pyridin-2-ones
Hong‐Yan Bi, Qing-Yan Wu, Xiaomei Zhou, Huijuan Xu, Cui Liang, Dong‐Liang Mo, Xiao‐Pan Ma
Abstract
We describe the difunctionalization of arylboronic acids to prepare various N-(2-hydroxyaryl)pyridin-2-ones in good yields using N-hydroxypyridin-2-ones as the oxygen and nitrogen sources through a copper(II)-catalyzed Chan–Lam reaction and subsequent BF3-promoted selective 1,3-rearrangement of N–O bond in a one-pot procedure. Mechanistic studies reveal that the 1,3-rearrangement selectivity is controlled by the formation of the key aryloxypyridinium salt. The obtained products are easily converted to various useful pyridin-2-one scaffolds.
Topics & Concepts
ChemistrySalt (chemistry)SelectivityLewis acids and basesMedicinal chemistryCombinatorial chemistryRearrangement reactionCopperStereochemistryCatalysisOrganic chemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsMulticomponent Synthesis of Heterocycles