AI Article Synopsis
- The study presents a new metal-free method for oxygenating aromatic C-H bonds using oxoammonium salts and water as the oxygen source, which could be beneficial for industrial and organic synthesis.
- Various alkyl-substituted phenols were successfully converted into benzoquinones with high yields ranging from 59% to 98%.
- The research suggests that the proposed mechanism involves an electrophilic aromatic substitution and could pave the way for developing more transition-metal-free catalytic techniques in the future.
Article Abstract
Aromatic C-H oxygenation is important in both industrial production and organic synthesis. Here we report a metal-free approach for phenol oxygenation with water as the oxygen source using oxoammonium salts as the renewable oxidant. Employing this protocol, various alkyl-substituted phenols were converted into benzoquinones in yields of 59-98%. On the basis of O-labeling and kinetic studies, the hydroxy-oxoammonium adduct was proposed to attack the aromatic ring similarly to electrophilic aromatic substitution. We suppose that the findings described here not only provide an efficient and highly selective protocol for aromatic C-H oxygenation but also may encourage further developments of possible transition-metal-free catalytic methods.
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| http://dx.doi.org/10.1021/acs.joc.3c02448 | DOI Listing |
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