Isomerically pure 5,11-dibromo-ADT was used to create contorted aromatics with large splay angles, low band gaps, and low LUMOs.

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.

The Banert Cascade of propargylic azides is a unique pathway to access α-functionalized NH-1,2,3-triazoles. The resulting het-erocycles have documented utility as unique bioisosteres. Previously, the scope of the nucleophile used...