2024/10/03 by D.B. Kim, Jaehyun You, D. H. Lee +3 · 1 voice
Chemistry · Pharmacology, Toxicology and Pharmaceutics · #Synthesis and Characterization of Pyrroles #Radical Photochemical Reactions #Fluorine in Organic Chemistry
paper · doi:10.1126/science.adq6245
openalex publication_date 2024/10/03 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/29
The identity of a heteroatom within an aromatic ring influences the chemical properties of that heterocyclic compound. Systematically evaluating the effect of a single atom, however, poses synthetic challenges, primarily as a result of thermodynamic mismatches in atomic exchange processes. We present a photocatalytic strategy that swaps an oxygen atom of furan with a nitrogen group, directly converting the furan into a pyrrole analog in a single intermolecular reaction. High compatibility was observed with various furan derivatives and nitrogen nucleophiles commonly used in drug discovery, and the late-stage functionalization furnished otherwise difficult-to-access pyrroles from naturally occurring furans of high molecular complexity. Mechanistic analysis suggested that polarity inversion through single electron transfer initiates the redox-neutral atom exchange processes at room temperature.