Palladium-catalyzed dearomative 1,4-hydroamination
Robert Gilbert1, Christopher W Davis1, Tanner W Bingham1
1Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL, 61801, USA.
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.
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