Silver Mediated Banert Cascade with Carbon Nucleophiles.

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_sp³-C_sp² and C_sp³-C_sp³ bonds under otherwise identical conditions from structurally dissimilar nucleophiles.

SUBMITTER: Alexander JR 

PROVIDER: S-EPMC8120647 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature