Alkali metal salts of 1,2,3-benzodiazaborines: platforms for late-stage <i>N</i>-functionalization and metal complexation.

ABSTRACT: The standard procedure for the preparation of benzoid 1,2,3-diazaborines (DABs) is the condensation of 2-formylphenyl boronic acid with a hydrazine. The choice of hydrazine derivative irreversibly predetermines the N-substituent in most cases and is additionally limited by the availability and hazardous nature of the respective hydrazines. Options to subsequently modify the N-substituent are scarce. Herein, we explore an approach to postsynthetic N-functionalization via isolable, nucleophilic DAB alkali metal amides. The structures of these metalated DABs were extensively studied, utilizing ¹H DOSY NMR spectroscopy and XRD analysis. Subsequent reactivity studies of these unusual amides revealed an intricate, dualistic reactivity pattern. Upon treatmen

SUBMITTER: Wust L 

PROVIDER: S-EPMC12053222 | biostudies-literature | 2025 Jun

REPOSITORIES: biostudies-literature