Transition-Metal-Free Oxidative Cross-Coupling of Triorganoindium Reagents with Tetrahydroisoquinolines

Gil-Negrete, J. M.; PĂ©rez Sestelo, J.; Sarandeses, L. A.


J. Org. Chem. 2019, 84, 9778-9785. DOI:

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Triorganoindium reagents (R3In) react with tetrahydroisoquinolines (THIQs) in the presence of Ph3CBF4 as oxidant to afford 1-substituted THIQs. The reaction proceeds in good yields at rt using 50 mol % of R3In with a variety of organic groups. 1H NMR studies show the generation of an iminium ion intermediate supporting a two-step mechanism based on THIQ oxidation and R3In nucleophilic addition. This reaction was applied to the synthesis of the alkaloid Nuciferine in three steps.