Strecker Reactions of Formaldehyde with TMSCN, Catalyzed by TBAF and Formic Acid: N‐Monocyanomethylation of Primary Amines

Abstract A set of conditions for the Strecker reaction of formaldehyde, amines, and TMSCN that affords three‐component coupling adducts as the major products is reported. HCOOH and TBAF are used as cocatalysts and the TMSCN functions as both cyanide source and protecting reagent for amines. As a result, the side reactions were suppressed efficiently and a broad range of aromatic and aliphatic amines were mono‐cyanomethylated in 52–99% yield. Furthermore, this protocol was successfully applied toward the synthesis of meta ‐diamide insecticides. magnified image