Product-Catalyzed Addition of Alkyl Nitriles to Unactivated Imines Promoted by Sodium Aryloxide/Ethyl(trimethylsilyl)acetate (ETSA) Combination

Autor: Poisson, Thomas, Gembus, Vincent, Oudeyer, Sylvain, Marsais, Francis, Levacher, Vincent
Zdroj: The Journal of Organic Chemistry; 20240101, Issue: Preprints p3516-3519, 4p
Abstrakt: The first transition-metal-free addition of alkyl nitriles to unactivated imines was developed using a catalytic combination of 4-MeOC6H4ONa and TMSCH2CO2Et to promote the reaction. The corresponding β-amino nitriles are obtained in good to almost quantitative isolated yields under mild conditions. A mechanism involving an autocatalytic pathway is proposed on the basis of experimental observations.
Databáze: Supplemental Index