Organocatalytic cyanosilylation of carbonyl compounds by tetrabutylammonium phthalimide-N-oxyl

Tetrabutylammonium phthalimide-N-oxyl (TBAPINO) was found to catalyze trimethylsilyl cyanide addition to a variety of aldehydes and ketones in high to excellent yields. The reaction proceeds smoothly under mild conditions by employing 1.0 mol% of the organocatalyst at room temperature within very short reaction times. Due to the high solubility of the tetrabutylammonium phthalimide-N-oxyl in organic solvents, a significant improvement in the catalytic activity of the phthalimide-N-oxyl (PINO) nucleophile was observed.