1,4-Dihydropyridine Anions as Potent Single-Electron Photoreductants

Abstract

We report the use of simple 1,4-dihydropyridine anions as a general platform for promoting single-electron photoreductions. In the presence of a mild base, 1,4-dihydropyridines were shown to effectively promote the hydrodechlorination and borylation of aryl chlorides and the photodetosylation of N-tosyl aromatic amines under visible light irradiation. Our studies also demonstrate that the C4 substituent can influence the reactivity of these anions, reducing unwanted side reactions like hydrogen atom transfer and back-electron transfer.