Photocatalytic Activation of Heterocyclic Iodonium Ylides for the Synthesis of Dihydrofuropyranones and Dihydrofuropyridones

β-Distabilized iodonium ylides undergo photocatalytic activation using neutral eosin Y and visible light to afford dihydrofuropyranones, dihydrofuropyridones, and dihydrofurans. Steady-state absorption spectroscopy and application of the method of continuous variations to complexation-induced chemical shifts provide evidence for the binary complexation of eosin Y and β-distabilized iodonium ylides. Preliminary mechanistic studies using transient absorption spectroscopy suggest monoanionic eosin Y as the active photocatalyst functioning via an oxidative quenching cycle. This simple approach to enhancing the reactivity of heterocyclic iodonium ylides expands the scope of their use as building blocks in the synthesis of heterocycles.

• Publication year

  2025

• Venue

  Journal of Organic Chemistry

• Publication date

  2025-09-11

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acs.joc.5c01187PMID 40934390PMCID 12481581
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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