figshare
Browse
ja8b05240_si_001.pdf (11.54 MB)

Asymmetric Photocatalytic C–H Functionalization of Toluene and Derivatives

Download (11.54 MB)
journal contribution
posted on 2018-06-22, 17:22 authored by Daniele Mazzarella, Giacomo E. M. Crisenza, Paolo Melchiorre
Reported herein is a visible-light-mediated organocatalytic direct C–H functionalization of toluene derivatives to afford enantioenriched β-benzylated aldehydes from the corresponding enals. The process combines the oxidative power of a chiral excited-state iminium ion and the basic nature of its counteranion to trigger the generation of benzylic radicals by means of a sequential multisite proton-coupled electron transfer mechanism. This study shows that feedstock chemicals generally used as solvents, such as toluene and xylene derivatives, can be used as substrates for making chiral molecules with high enantioselectivity.

History