An expeditious synthesis of cyanohydrin trimethylsilyl ethers using tetraethylammonium 2-(carbamoyl)benzoate as a bifunctional organocatalyst

Phthalimide and tetraethylammonium hydroxide react via an unusual pathway to afford tetraethylammonium 2-(carbamoyl)benzoate (TEACB) which is of interest as a bifunctional organocatalyst. TEACB (0.5 mol %) was found to catalyze the addition of trimethylsilyl cyanide (TMSCN) to carbonyl compounds under solvent-free conditions at room temperature with very short reaction times. A wide variety of aldehydes and ketones were transformed into the corresponding cyanohydrin trimethylsilyl ethers in high to quantitative yields.

Graphical abstractTetraethylammonium 2-(carbamoyl)benzoate (TEACB) was found to be an effective bifunctional organocatalyst for rapid and clean cyanosilylation of carbonyl compounds under solvent-free conditions.Download full-size image