Development of d2-Benzylating Reagents Based on Pyridinium Salts
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Updated: Nov 7, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Ryunosuke Akazawa1, Kazuho Ban1, Yoshinari Sawama1
1Graduate School of Pharmaceutical Sciences, The University of Osaka, 1-6 Yamadaoka, Suita, Osaka565-0871, Japan.
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.
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