Perfectly green organocatalysis: Quaternary ammonium base triggered cyanosilylation of aldehydes

Abstract

Quaternary ammonium bases, such as aqueous (CH 3) 4NOH, were found to be an extraordinarily efficient catalyst for cyanosilylation of aldehydes. The addition reaction of trimethylsilyl cyanide (TMSCN) to equivalent aldehydes could proceed smoothly with turnover frequency (TOF) up to 3000000 h -1 and in near 100% yield under solvent-free conditions. These organic catalysts also tolerated various aldehydes including aromatic, aliphatic and α,β-unsaturated aldehydes. This process perfectly conforms to the features of green chemistry: no waste regarding side-products and unconverted reactants, solvent-free, excellent catalytic activity, and no requirement for separation. © 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.