Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative to the Staudinger/Aza-Wittig Reaction

The traditional Staudinger/aza-Wittig reaction represents one of the most powerful tools for imine formation. However, for this multistep procedure, the sacrificial phosphine has to be used, resulting in difficulties in the purification process and waste disposal at the same time. Here, we report a redox-neutral azide-alcohol imination methodology enabled by a base-metal nickel PN3 pincer catalyst. The one-step, waste-free, and high atom-economical features highlight its advantages further. Moreover, mechanistic insight suggests a non-metal-ligand cooperation pathway based on the observation of an intermediate and density functional theory calculations.

Automated summary

The new imination methodology with a base-metal nickel PN3 pincer catalyst features one-step, waste-free, and high atom-economical characteristics, avoiding the difficulties in purification and waste disposal in traditional methods. Mechanistic insight reveals a non-metal-ligand cooperation pathway, providing an important theoretical basis for modern organic synthesis.