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