HCl‐Catalyzed Aerobic Oxidation of Alkylarenes to Carbonyls

The construction of C−O bonds through C−H bond functionalization remains fundamentally challenging. Here, a practical chlorine radical‐mediated aerobic oxidation of alkylarenes to carbonyls was developed. This protocol employed commercially available HCl as a hydrogen atom transfer (HAT) reagent and...

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Bibliographic Details
Published in:ChemSusChem 2022-01, Vol.15 (2), p.e202102326-n/a
Main Authors: Niu, Kaikai, Shi, Xiaodi, Ding, Ling, Liu, Yuxiu, Song, Hongjian, Wang, Qingmin
Format: Article
Language:English
Subjects:
aerobic oxidation
alkylarenes
Carbonyls
Catalysis
Chlorine
Functional groups
Hydrogen
Hydrogen bonds
Indicators and Reagents
metal-free
Oxidants
Oxidation
Oxidation-Reduction
Oxidizing agents
photochemistry
Reagents
Substrates
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Summary:The construction of C−O bonds through C−H bond functionalization remains fundamentally challenging. Here, a practical chlorine radical‐mediated aerobic oxidation of alkylarenes to carbonyls was developed. This protocol employed commercially available HCl as a hydrogen atom transfer (HAT) reagent and air as a sustainable oxidant. In addition, this process exhibited excellent functional group tolerance and a broad substrate scope without the requirement for external metal and oxidants. The mechanistic hypothesis was supported by radical trapping, 18O labeling, and control experiments. Metal‐free: A simple and practical chlorine radical‐mediated aerobic oxidation of alkylarenes to carbonyls under metal‐free conditions is developed. The process exhibits excellent functional group tolerance and a broad substrate scope without the requirement for external metal and oxidants.
ISSN:1864-5631
1864-564X
DOI:10.1002/cssc.202102326