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Photocatalytic furan-to-pyrrole conversion
Science ( IF 44.7 ) Pub Date : 2024-10-03 , DOI: 10.1126/science.adq6245 Donghyeon Kim, Jaehyun You, Da Hye Lee, Hojin Hong, Dongwook Kim, Yoonsu Park
Science ( IF 44.7 ) Pub Date : 2024-10-03 , DOI: 10.1126/science.adq6245 Donghyeon Kim, Jaehyun You, Da Hye Lee, Hojin Hong, Dongwook Kim, Yoonsu Park
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.
更新日期：2024-10-03
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