Organic Letters· 2026Q1
Harnessing Diazo Compounds as Alkoxycarbonyl Methylene Radical Linchpins: Truce–Smiles Rearrangement toward Amido Esters and Isoquinolinedione Scaffolds
- 1citations
- Q1SCImago
- 2026year
Short summary
A photochemical Truce–Smiles rearrangement of N-aryl-N-arylsulfonyl acrylamides using diazo compounds as radical precursors yields β,β′-disubstituted amido esters and isoquinolinediones.
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Key points
- Diazo compounds are used as radical precursors in a photochemical Truce–Smiles rearrangement.
- The reaction yields β,β′-disubstituted amido esters from N-aryl-N-arylsulfonyl acrylamides.
- The protocol can be adapted to synthesize isoquinolinediones exhibiting atropisomerism.
- A radical-mediated proton-coupled electron transfer (PCET) mechanism involving intramolecular aryl radical migration is proposed.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract The radical reactivity of acceptor-type diazo compounds is harnessed in the photochemical Truce–Smiles rearrangement of N-aryl-N-arylsulfonyl acrylamides to access β,β′-disubstituted amido esters. The rational design of starting materials and the cascade technique can be extended to yield isoquinolinediones to display atropisomerism. Mechanistic investigations support a radical-mediated proton-coupled electron transfer (PCET) process involving intramolecular migration of an aryl radical via a spiro intermediate. This protocol shows the untapped potential of diazo chemistry for radical-based transformations beyond traditional carbene pathways.
The authors' abstract, as published at the source. Organic Letters, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry