Product-catalyzed addition of alkyl nitriles to unactivated imines promoted by sodium aryloxide/ethyl(trimethylsilyl)acetate (ETSA) combination.
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.
Poisson
Thomas
T
Chimie Organique, Bioorganique, Réactivité et Analyse (UMR6014), CNRS, Université et INSA de Rouen, IRCOF, BP08, F-76131Mont-Saint-Aignan Cedex, France.
Gembus
Vincent
V
Oudeyer
Sylvain
S
Marsais
Francis
F
Levacher
Vincent
V
D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D012964:Sodium / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D007097:Imines; D009570:Nitriles; D009942:Organometallic Compounds; D014297:Trimethylsilyl Compounds; C043884:2-(trimethylsilyl)ethyl acetate; D012964:Sodium