Asymmetric benzylic C(sp³)-H acylation via dual nickel and photoredox catalysis.

ABSTRACT: Asymmetric C(sp³)-H functionalization is a persistent challenge in organic synthesis. Here, we report an asymmetric benzylic C-H acylation of alkylarenes employing carboxylic acids as acyl surrogates for the synthesis of α-aryl ketones via nickel and photoredox dual catalysis. This mild yet straightforward protocol transforms a diverse array of feedstock carboxylic acids and simple alkyl benzenes into highly valuable α-aryl ketones with high enantioselectivities. The utility of this method is showcased in the gram-scale synthesis and late-stage modification of medicinally relevant molecules. Mechanistic studies suggest a photocatalytically generated bromine radical can perform benzylic C-H cleavage to activate alkylarenes as nucleophilic coupling partners which can then engage i

SUBMITTER: Huan L 

PROVIDER: S-EPMC8192574 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature