Organic Letters· 2026Q1
Intramolecular [4 + 2] Cycloaddition via Photoredox Dual Dearomatization of Indole and Furan Units
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- Q1SCImago
- 2026year
Short summary
A photoredox-catalyzed intramolecular dual dearomatization reaction constructs four fused rings from indole and furan units in one step.
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Key points
- Developed an intramolecular dual dearomatization of indoles and furans using photoredox catalysis.
- Enables the construction of four fused rings in a single step with high regio- and diastereoselectivity.
- Products can be converted to furan-fused polycyclic scaffolds via a one-pot procedure with p-toluenesulfonic acid.
- Demonstrated synthetic utility through gram-scale synthesis and downstream transformations.
- Mechanistic studies indicate a single-electron transfer (SET) pathway.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract Despite significant advances in the field of dearomatization, dual dearomatization remains underdeveloped. Herein, we report an intramolecular dual dearomatization reaction of indoles and furans by photoredox catalysis. This method enables the construction of four fused rings in a single step with exceptional regio- and diastereoselectivities under mild conditions. The products can be converted into furan-fused polycyclic scaffolds in a one-pot procedure by using p-toluenesulfonic acid. The synthetic utility of this approach was demonstrated through gram-scale synthesis and several downstream transformations. Mechanistic studies revealed that this reaction proceeds via a single-electron transfer (SET) pathway rather than an energy transfer pathway.
The authors' abstract, as published at the source. Organic Letters, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry