Construction of Functionalized Oxindoles by Quinone-Carbonate Synergistically Triggered Intermolecular Radical
Yun Qiu1, Zecheng Wu1, Xingyun Ou1
1College of Chemistry and Materials Science, Jinan University, Guangzhou, Guangdong 511443, China.
Abstract:
We disclose a rapid and nontoxic procedure to construct various oxindoles. This method harnesses the power of a catalytic amount of quinone in synergy with Cs2CO3, showcasing remarkable compatibility with a wide range of functional groups. Mechanistic investigations reveal that it operates via a radical pathway, likely initiated by the single-electron transfer from quinone-Cs2CO3 complexes. This pivotal electron transfer event leads to the generation of a crucial alkyl radical intermediate, contributing to the overall success and efficacy of the transformation.
Related Concept Videos
Oxidation of Phenols to Quinones
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Radical Reactivity: Overview
Radical Reactivity: Intramolecular vs Intermolecular
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Radical Oxidation of Allylic and Benzylic Alcohols


