Visible-Light-Induced Metal-Free Allylic Oxidation Utilizing a Coupled Photocatalytic System of g-C3N4 and N-Hydroxy Compounds

• Published in: Advanced synthesis & catalysis Vol. 353; no. 9; pp. 1447 - 1451
• Main Authors: Zhang, Pengfei, Wang, Yong, Yao, Jia, Wang, Congmin, Yan, Chao, Antonietti, Markus, Li, Haoran
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.06.2011; WILEY‐VCH Verlag; Wiley-VCH
• Subjects: Activation; Aldehydes; carbon nitride; Catalysis; Catalysts; Chemical reactivity; Chemistry; CH activation; Derivatives; Exact sciences and technology; Free radicals chemistry; General and physical chemistry; Kinetics and mechanisms; metal-free oxidation; N-hydroxyphthalimide; NHPI; Organic chemistry; Oxidation; Photocatalysis; Photochemistry; photooxidation; Physical chemistry of induced reactions (with radiations, particles and ultrasonics); Reactivity and mechanisms; Semiconductors; metal-free oxidation; Mild operating conditions; Selectivity; Metal; Allylic compound; Imide; Oxygen molecules; Visible radiation; Reaction mechanism; Oxidation; Chemical reactivity; NHPI; photooxidation; Carbon Nitrides; Catalytic reaction; Nitroxyl; Semiconductor materials; Stability; Carbon-hydrogen bond; Chemical bond; Photocatalysis; Toluene; Aldehyde; N-hydroxyphthalimide; C―H activation; carbon nitride; Organic free radical; Graphite; Alkalinity; Photooxidation
• ISSN: 1615-4150; 1615-4169; 1615-4169
• DOI: 10.1002/adsc.201100175

Graphitic carbon nitride (g‐C3N4) and N‐hydroxy compounds can function as a non‐metal photocatalytic system to activate O2 for the selective allylic oxidation under mild conditions, avoiding the employment of any metal derivative or organic oxidizing agents. Interestingly, the novel photocatalytic system affords a remarkably high selectivity towards the formation of aldehydes, especially in the oxidation of toluene. By combining the unique nature of g‐C3N4 (surface basicity, semiconductor features, high stability) and the remarkable catalytic oxidation reactivity of nitroxyl radicals, this photocatalytic system opens up a mild and efficent access for CH bond activation.