Discovery of the Quinoxalinone–B(C₆F₅)₃·H₂O Combo as a Photocatalyst by Acidochromism Strategy: Aerobic Oxidation of Alcohol, Alkene, and Thiols

Abstract

Modification of photocatalyst reactivity through intermolecular interactions represents a straightforward and convenient strategy for catalyst designation. Herein, we reported that upon the addition of B(C6F5)3·H2O, the oxidation potential of quinoxalinone increased remarkably, enabling the photoredox aerobic oxidation of alcohol, thiols, and alkenes toward carbonyl compounds and dithioethers under visible light conditions. Mechanistic studies, including X-ray structure analysis, cyclic voltammetry, electron paramagnetic resonance measurements, UV–vis absorption, and fluorescence spectra, revealed that the quinoxalinone–B(C6F5)3·H2O combo could serve as a versatile photocatalyst for both energy transfer and single electron transfer processes.

Radical reactions enabled by polyfluoroaryl fragments: photocatalysis and beyond

“…For example, the complex of borane hydrate with quinoxalinone catalyzes the aerobic photooxidation of alkenes, benzyl alcohols, and thiols (Scheme 104). 233…”