Silver Mediated Banert Cascade with Carbon Nucleophiles

The Banert cascade of propargylic azides can be promoted by simple silver salts, and the triazafulvene intermediate can be intercepted by carbon nucleophiles. Various indoles (>25 examples, up to 92% yield) and electron-rich heterocycles were effective. The Mayr nucleophilicity parameter (N) was found to correlate to the reaction efficiency, which enabled the formation of C-sp(3)-C-sp(2) and C-sp(3)-C-sp(3) bonds under otherwise identical conditions from structurally dissimilar nucleophiles.

Automated summary

The Banert cascade reaction of propargylic azides can be promoted by simple silver salts, leading to the formation of various indoles and electron-rich heterocycles. The correlationship between the Mayr nucleophilicity parameter (N) and the reaction efficiency enables the formation of C-sp(3)-C-sp(2) and C-sp(3)-C-sp(3) bonds under otherwise identical conditions from structurally dissimilar nucleophiles.