C(sp 3 )-H Alkenylation of Tetrahydroisoquinolines via Merging Electrochemistry and Organocatalysis.

C(sp 3 )-H alkenylation of tetrahydroisoquinoline by merging Shono oxidation and the Morita-Baylis-Hillman reaction is developed, employing 4-dimethylaminopyridine as an organocatalyst and TEMPO/NaBr as an electrocatalyst. The reaction proceeds via the interception of an iminium cation intermediate, which is generated in situ from anodic oxidation, leading to aza-Morita-Baylis-Hillman reaction products. Additionally, the use of TEMPO and NaBr as mediators is crucial to avoid the decomposition of products by lowering the oxidation potential of the reaction.