A Horseradish Peroxidase-Mediator System for Benzylic C-H Activation.

ABSTRACT: Enzyme-mediator systems generate radical intermediates that abstract hydrogen atoms under mild conditions. These systems have been employed extensively for alcohol oxidation, primarily in biomass degradation, but they are underexplored for direct activation of C(sp³)-H bonds in alkyl groups. Here, we combine horseradish peroxidase (HRP), H₂O₂, and redox mediator N-hydroxyphthalimide (NHPI) for C(sp³)-H functionalization of alkylbenzene-type substrates. The HRP-NHPI system is >10-fold more active than existing enzyme-mediator systems in converting alkylbenzenes to ketones and aldehydes under air, and it operates from 0-50 °C and in numerous aqueous-organic solvent mixtures. The benzylic substrate radical can be trapped through a reaction with NHPI

SUBMITTER: Cribari MA 

PROVIDER: S-EPMC10162642 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature