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

Thomas Poisson (1) , Vincent Gembus (1) , Sylvain Oudeyer (1) , Francis Marsais (1) , Vincent Levacher (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

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.

Domains: Chemical Sciences; Organic chemistry

Thomas Poisson, Vincent Gembus, Sylvain Oudeyer, Francis Marsais, Vincent Levacher. Product-Catalyzed Addition of Alkyl Nitriles to Unactivated Imines Promoted by Sodium Aryloxide/Ethyl(trimethylsilyl)acetate (ETSA) Combination. Journal of Organic Chemistry, 2009, 74 (9), pp.3516-3519. ⟨10.1021/jo802763b⟩. ⟨hal-02278746⟩