Two case studies demonstrate how a Bronsted basic auxiliary can stabilize electropositive species. (1) Aza-quaternary centers are important structural motifs in nature, but they can be challenging to synthesize. We demonstrate that proton transfer into a basic auxiliary offsets a challenging C-N formation, generating aza-quaternary centers via the amination of catechol derivatives. (2) Similar principles result in the stabilization of an iron-aquo coordination complex.

Brønsted basic auxiliary enables synthesis of aza-quaternary centers and metal-aquo complexes

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