Abstract
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.