A versatile catalyst-free redox system mediated by carbon dioxide radical and dimsyl anions

Abstract

The development of new, efficient ways to initiate redox events has long been a goal in organic synthesis. A redox system mediated by carbon dioxide radical and dimsyl anions is demonstrated and a variety of transformations, including hydrocarboxylation, hydroxycarboxylation, Birch reduction, and three-component reductive coupling of carbonyl compounds, amines, and cyanopyridines, are achieved in a catalyst-free fashion using this method, giving valuable acids, saturated skeletons, and α-pyridyl amines in high efficiency. This strategy promises wide applications in other types of reactions and complements current photoredox catalysis methodologies.