Organic Letters· 2026Q1
Skeletal Modification of Tryptophan Using Cyclic Diaryliodonium Salts via Palladium-Catalyzed Cascade π-Extended Annulative Dual C2–H/N–H Arylation
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- Q1SCImago
- 2026year
Short summary
A new palladium-catalyzed reaction modifies the tryptophan skeleton into phenanthridinyl indole using cyclic diaryliodonium salts.
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Key points
- Developed a Pd-catalyzed annulative dual C2–H/N–H arylation reaction.
- Modifies the tryptophan indole skeleton to phenanthridinyl indole.
- Ligand-free strategy applicable to indole derivatives and short peptides.
- Yields diverse unnatural phenanthridinyl indole-tethered peptides efficiently.
- Tolerates N- and C-terminal protecting groups and side-chain functionalities.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract We have demonstrated an efficient Pd-catalyzed annulative dual C2–H/N–H arylation reaction involving modification of the tryptophan indole skeleton to phenanthridinyl indole. This is an operationally simple and ligand-free strategy that was extended to biologically important indole derivatives and tryptophan-containing short peptides to deliver a diverse unnatural phenanthridinyl indole-tethered peptide with good efficiency. Notably, the method demonstrated good tolerance for N- and C-terminal protecting groups as well as for the side-chain functionalities of other amino acids.
The authors' abstract, as published at the source. Organic Letters, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry