Electroreductive Radical Borylation of Unactivated (Hetero)Aryl Chlorides Without Light by Using Cumulene-Based Redox Mediators.

ABSTRACT: Single-electron transfer (SET) plays a critical role in many chemical processes, from organic synthesis to environmental remediation. However, the selective reduction of inert substrates (E_p/2 <-2 V vs Fc/Fc⁺ ), such as ubiquitous electron-neutral and electron-rich (hetero)aryl chlorides, remains a major challenge. Current approaches largely rely on catalyst photoexcitation to reach the necessary deeply reducing potentials or suffer from limited substrate scopes. Herein, we demonstrate that cumulenes-organic molecules with multiple consecutive double bonds-can function as catalytic redox mediators for the electroreductive radical borylation of (hetero)aryl chlorides at relatively mild cathodic potentials (approximately -1.9 V vs. Ag/AgCl) without the need for photoirr

SUBMITTER: Lai Y 

PROVIDER: S-EPMC10529720 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature