Gilbert, Robert; Davis, Christopher W; Bingham, Tanner W; Sarlah, David

DOI:

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.

Keywords

Dearomatization ; Hydroamination ; Arenophiles ; Palladium ; Catalysis

Purchased from AmBeed