Photo-tunable oxidation of toluene and its derivatives catalyzed by TBATB

• Published in: Journal of photochemistry and photobiology. A, Chemistry. Chemistry., 2021-06, Vol.414, p.113301, Article 113301
• Main Authors: Mardani, Atefeh, Kazemi, Foad, Kaboudin, Babak
• Format: Article
• Language: English
• Subjects: Benzoic acid; Photooxidation; Tetrabutylammonium tribromide; Toluene; Tunable synthesis; Visible light photocatalyst
• ISSN: 1010-6030; 1873-2666
• DOI: 10.1016/j.jphotochem.2021.113301

[Display omitted] •Selective aerobic photooxidation of toluenes to benzaldehydes and benzoic acid in good to high yield.•Visible light-controlled selectivity to products in aerobic photooxidation.•Visible light: blue (460 nm) and violet (400 nm) LED. In this report, tetrabutylammonium tribromide (TBATB) was introduced as an efficient visible light active catalyst to carry out the aerobic oxidation of toluene, its derivatives, and some of methyl arenes to benzaldehydes, benzoic acids and ketones in good to high yields. All the oxidation reactions were performed under mild conditions using oxygen as a green oxidant, a catalytic amount of TBATB under blue (460 nm), royal blue (430 nm), and violet LED (400 nm) irradiation. It was found that the reactions selectivity was significantly affected by changing the solvent (from CH3CN to EtOAc) and LED wavelength (from blue to violet). In the following, our mechanistic studies revealed that the visible light oxidation of toluenes and methyl arenes over TBATB could be following a benzyl peroxy radical intermediate.