Palladium-catalyzed dearomative 1,4-hydroamination

Abstract

A dearomative 1,4-hydroamination of nonactivated arenes has been developed, using a key arene–arenophile photocycloaddition strategy to disrupt aromaticity. Palladium catalysis with K-Selectride® as a hydride source uniquely enables selective reactivity and provides access to a range of substituted 1,4-cyclohexadienes from aromatic starting materials. We demonstrate a few synthetic applications of this scalable procedure by preparing highly-functionalized small molecules in three to four steps from naphthalene.