Generation of a Cation Radical from 2-Pivaloyl-1-tributylstannyl-1,2,3,4-tetrahydroisoqumoline and the Reaction with Carbon Nucleophiles

Oxidation of 2-pivaloyl-1-tributylstannyl-1,2,3,4-tetrahydroisoquinoline with metallic oxidants generates a reactive species such as the hydroisoquinolin-1-yl cation by eliminating the stannyl group. This intermediate reacts with various carbon nucleophiles to give the corresponding addition products.