Redox-Switchable Halogen Bonding in Haloanthracene Mediators Enables Efficient Electrocatalytic C-N Coupling.

ABSTRACT: We report the development of redox mediators based on 9-halo-10-arylanthracenes that engage in halogen bonding only upon one-electron oxidation. This redox-switchable interaction enables an effective substrate preorganization and promotes intramolecular C-N bond formation via electrocatalysis. Systematic evaluation of halogenated mediators (1a-1c) across various N-protected 2-aminobiphenyl substrates revealed that the iodoanthracene derivative 1a exhibited superior catalytic performance. Building on this, we synthesized a series of 10-aryl-substituted iodoanthracenes (1d-1h) to further optimize the mediator structure. Kinetic analysis by foot-of-the-wave analysis identified 1h, bearing a 3,5-bis(trifluoromethyl)phenyl group, as a highly active mediator wi

SUBMITTER: Hirama A 

PROVIDER: S-EPMC12921847 | biostudies-literature | 2026 Feb

REPOSITORIES: biostudies-literature