Organophotocatalytic Regioselective Silylation/Germylation and Cascade Cyclization of N-Alkenyl α-CF3 Acrylamides: Access to Densely Functionalized 4-Pyrrolin-2-ones

Abstract

We report an organophotoredox-catalyzed silylation/germylation cascade cyclization of N-alkenyl α-CF3 acrylamides under mild conditions. N-Aminopyridinium salts act as hydrogen atom transfer reagents under photoredox catalysis in the generation of silyl and germyl radicals. An array of silyl- and germyl-substituted 3-CF3-4-pyrrolin-2-one derivatives were constructed in a shorter reaction time with low catalyst loading in good to excellent yields at room temperature. Importantly, this protocol is amenable to the late-stage diversification of bioactive molecules, as well as to large-scale synthesis. © 2024 American Chemical Society.