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 Csp3–Csp2 and Csp3–Csp3 bonds under otherwise identical conditions from structurally dissimilar nucleophiles.