Metal-Free Aerobic C–H Oxidation of Methylarenes to Aromatic Aldehydes by Sulfur-Containing Tetracyclic Compounds as Visible-Light Photocatalysts

Oxidation of benzylic sp3 C–H bonds smoothly proceeded at ambient temperature under blue LED (465 nm) photo-irradiation using sulfur-containing tetracyclic compounds as photocatalysts. The use of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as a co-solvent was the key to success: various toluene derivat...

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Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan 2022-05, Vol.95 (5), p.768-770
Main Authors: Shibata, Takanori, Akino, Mika, Sekine, Ayato, Ito, Mamoru
Format: Article
Language:English
Subjects:
Aldehydes
Ambient temperature
Chemical bonds
Electron paramagnetic resonance
Electron spin
Oxidation
Photocatalysts
Spin resonance
Sulfur
Toluene
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Summary:Oxidation of benzylic sp3 C–H bonds smoothly proceeded at ambient temperature under blue LED (465 nm) photo-irradiation using sulfur-containing tetracyclic compounds as photocatalysts. The use of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as a co-solvent was the key to success: various toluene derivatives were selectively oxidized to substituted benzaldehydes without over-oxidation. Preliminary mechanism studies were undertaken, including electron spin resonance (ESR) spectroscopy analyses.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20220014