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

• Published in: Organic letters Vol. 25; no. 30; pp. 5613 - 5618
• Main Authors: Huang, Jie, Luo, Yun-Xuan, Wang, Long, Tang, Xiang-Ying
• Format: Journal Article
• Language: English
• Published: American Chemical Society 04-08-2023
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/acs.orglett.3c01977

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.