An efficient and practical aerobic oxidation of benzylic methylenes by recyclable N-hydroxyimide

An efficient and practical benzylic aerobic oxidation catalyzed by cheap and simple N-hydroxyimide organocatalyst has been achieved with high yields and broad substrate scope. The organocatalyst used can be recycled and reused by simple workup and only minute amount (1 mol% in most cases) of simple iron salt is used as promoter. Phenyl substrates with mild and strong electron-withdrawing group could also be oxygenated in high yields as well as other benzylic methylenes. Influence of substituents, gram-scale application, catalysts decay and general mechanism of this methodology has also been discussed.

Automated summary

The benzylic aerobic oxidation catalyzed by cheap and simple N-hydroxyimide organocatalyst is efficient and practical, with high yields and broad substrate scope. The catalyst can be recycled, and only a small amount of simple iron salt is used as promoter. This methodology also discusses the influence of substituents, gram-scale application, catalyst decay, and the general mechanism.