ja8b05240_si_001.pdf (11.54 MB)
Asymmetric Photocatalytic C–H Functionalization of Toluene and Derivatives
journal contribution
posted on 2018-06-22, 17:22 authored by Daniele Mazzarella, Giacomo E. M. Crisenza, Paolo MelchiorreReported 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.
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enantioselectivityvisible-light-mediated organocatalyticgenerationenalchiral moleculesFunctionalizationDerivatives ReportedAsymmetricnaturexylene derivativesfunctionalizationToluenebenzylic radicalssolventPhotocatalyticenantioenriched β- benzylated aldehydestoluene derivativesfeedstock chemicalssubstrateoxidative powercounteranionchiral excited-state iminium ionsequential multisite proton-coupled electron transfer mechanism
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