Momentary click nitrile synthesis enabled by an aminoazanium reagent

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.

Automated summary

In this study, a novel nitrile synthesis method was reported, which efficiently converts functionalized aldehydes to nitriles within 5 minutes at room temperature by utilizing a stable and robust aminoazanium reagent. The stability and speed of this method make the CHO group equivalent to CN in organic synthesis, and it can also be used for direct cyanation of various aldehyde precursors through a cyanide-free process. The developed method not only provides a rapid access to a wide range of ligands and material precursors, but also offers a potential application for the late-stage modification of complex bioactive molecules.