Transformation of Benzaldehydes to Benzonitriles via Cyanophosphates without One-Carbon Homologation

Abstract

AbstractThe transformation of benzaldehydes into benzonitriles via cyanophosphates (CPs) with tetrabutylammonium azide (Bu4N·N3) was found to afford a range of benzonitriles in modest-to-high yields. As the CN-carbon of benzonitriles arises from the formyl-carbon of benzaldehydes, this is a new type of CP-reaction, distinctly different from the past one-carbon nitrile homologation. In contrast, the reaction of ketone- or aliphatic aldehyde-CPs with Bu4N·N3 resulted in mono-deethylaton forming tetrabutylammonium salts.