jo7b02584_si_001.pdf (13.19 MB)
Tropylium-Promoted Oxidative Functionalization of Tetrahydroisoquinolines
journal contribution
posted on 2017-12-12, 00:00 authored by Giulia Oss, Sander D. de Vos, Kevin N. H. Luc, Jason B. Harper, Thanh V. NguyenStructural
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.