Aminoborate-Catalyzed Reductive Counterreactions for Oxidative Electrosynthetic Transformations.

ABSTRACT: Electrooxidative transformations frequently rely on proton reduction as the terminal electron sink. However, this cathodic counterreaction can be slow in organic solvents and can operate at reducing potentials that are incompatible with catalysts and reagents needed for oxidative reactions. We report aminoborate adducts as redox mediators for proton reduction that operate at mild reducing potentials. This reliable cathodic couple ultimately enables successful oxidative organic transformations, including chlorodeborylation, developed herein, and Cu-catalyzed Chan-Lam coupling, reported previously by our group. Pyridinium borate adducts formed during electrooxidative chlorination of aryl trifluoroborates serve as easily reduced complexes (-1.1 V vs Fc/Fc⁺) to catalyze proton reduc

SUBMITTER: Smith RE 

PROVIDER: S-EPMC11661924 | biostudies-literature | 2024 Dec

REPOSITORIES: biostudies-literature