Organic Letters· 2026Q1
Development of d 2-Benzylating Reagents Based on Pyridinium Salts
- 1citations
- Q1SCImago
- 2026year
Short summary
New d2-benzyl pyridinium salts efficiently benzylate nucleophiles and generate radicals for synthesis, enabling selective access to deuterated methyl arenes.
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Key points
- N-Benzyl Katritzky salts efficiently undergo H/D exchange at the benzylic C–H position with D2O under basic conditions.
- Iodination of d2-benzyl Katritzky salts yields electrophilic d2-benzylation reagents for diverse nucleophiles.
- Photochemical conditions generate d2-benzyl radicals from these salts, which add to heterocycles, olefins, and alkynes.
- Reductive deamination allows selective synthesis of d1-, d2-, and d3-methyl arenes.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract N-Benzyl Katritzky salts undergo highly efficient (>99%) H/D exchange at the benzylic C–H position upon treatment with D2O under basic conditions, giving d2-benzyl Katritzky salts bearing electron-neutral or electron-deficient aryl groups. Via iodination, these serve as electrophilic d2-benzylation reagents for various nucleophiles in high yield. Under photochemical conditions, they generate d2-benzyl radicals that add to heterocycles, olefins and alkynes. Reductive deamination provides selective access to d1-, d2-, and d3-methyl arenes, which are useful for deuterated drug synthesis.
The authors' abstract, as published at the source. Organic Letters, 2026 · DOI ↗
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Field: Pharmaceutical Science
Pharmaceutical SciencePharmacology, Toxicology and Pharmaceutics