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Tropylium-Promoted Oxidative Functionalization of Tetrahydroisoquinolines

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journal contribution
posted on 12.12.2017, 00:00 authored by Giulia Oss, Sander D. de Vos, Kevin N. H. Luc, Jason B. Harper, Thanh V. Nguyen
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.