Tropylium-Promoted Oxidative Functionalization of Tetrahydroisoquinolines
Giulia Oss1, Sander D de Vos1, Kevin N H Luc1
1School of Chemistry, University of New South Wales , Sydney, Australia.
Abstract:
Structural modification of the tetrahydroisoquinoline (THIQ) framework is of significant interest to organic chemists due to its central role in heterocyclic and medicinal chemistry. Here we demonstrate an efficient metal-free method for the oxidative functionalization of THIQs at the C1 position, which is amenable to a diverse range of C-C coupling reactions. These reactions proceed through a hydride abstraction involving the tropylium ion followed by quenching the generated iminium intermediates with nucleophiles to afford THIQ derivatives with excellent efficiencies and interesting selectivities.
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