Benzylic Hydroperoxidation via Visible-Light-Induced Csp3-H Activation

J Org Chem. 2020 May 1;85(9):6181-6187. doi: 10.1021/acs.joc.0c00385. Epub 2020 Apr 17.

Abstract

A highly efficient benzylic hydroperoxidation has been realized through a visible-light-induced Csp3-H activation. We believe that this reaction undergoes a direct HAT mechanism catalyzed by eosin Y. This approach features the use of a metal-free catalyst (eosin Y), an energy-economical light source (blue LED), and a sustainable oxidant (molecular oxygen). Primary, secondary, and tertiary hydroperoxides as well as silyl, benzyl, and acyl peroxides were successfully prepared with good yields and excellent functional group compatibility.