Poisson T1, Gembus V, Oudeyer S, Marsais F, Levacher V.
J Org Chem. 2009 May 1;74(9):3516-9. doi: 10.1021/jo802763b.The first transition-metal-free addition of alkyl nitriles to unactivated imines was developed using a catalytic combination of 4-MeOC(6)H(4)ONa and TMSCH(2)CO(2)Et to promote the reaction. The corresponding beta-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.