Organic Letters· 2026Q1
Photoredox/Cobalt-Catalyzed Cascade Rearrangement-Cyclization of Alkene
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- Q1SCImago
- 2026year
Short summary
A novel photoredox/cobalt-catalyzed cascade reaction achieves selective 1,2-aryl migration followed by cyclization in unactivated alkenes, yielding diverse spirocyclic and heterocyclic compounds.
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Key points
- Developed a photoredox/cobalt-catalyzed cascade reaction for unactivated alkenes.
- Achieves selective 1,2-aryl migration followed by intramolecular cyclization.
- Mechanism involves metal-hydride hydrogen atom transfer and radical-polar crossover.
- DFT calculations explain the preference for aryl migration.
- Enables synthesis of diverse spirocyclic and heterocyclic compounds.
AI-generated from the title and abstract; the full text is not read.
Abstract
A photoredox/cobalt-catalyzed sequential rearrangement-cyclization of unactivated alkenes is reported. 1,1diarylalkenes bearing tethered nucleophiles undergo a selective 1,2-aryl migration, initiated by metal-hydride hydrogen atom transfer and radical-polar crossover, and followed by intramolecular cyclization. Evaluating the catalytic reaction manifolds suggested that this system offers high reactivity and migratory selectivity. The preference for the 1,2-aryl shift over direct cyclization was rationalized by DFT calculations. This catalytic protocol enables accessing diverse spirocyclic and heterocyclic architectures.
The authors' abstract, as published at the source. Organic Letters, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry