Momentary click nitrile synthesis enabled by an aminoazanium reagent

Abstract

Achieving fast and selective functional group interconversion is crucial for improving synthetic efficiency in chemical science nowadays. In this context, we report momentary and selective Schmidt-type nitrile synthesis. The success of this achievement is ascribed to the employment of the stable and robust aminoazanium reagent H₂N-DABCO. A broad range of functionalized aldehydes were efficiently converted to nitriles within 5 min at room temperature in air. The robustness and speed of the protocol allow the CHO group to be regarded as a CN equivalent in organic synthesis. Moreover, the synthetic advantage of this developed protocol is further highlighted via the direct cyanation of a diversity of aldehyde precursors (carboxylic acids, aromatics, aryl halides, alkenes, and alkynes) in a cyanide-free process. Additionally, we show that this protocol can not only be used for rapid access to a wide range of ligands and material precursors, but it can also be used in the late-stage modification of complex bioactive molecules.