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

Leitao Huan, Xiaomin Shu, Weisai Zu, Zhong De and Haohua Huo ()
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Leitao Huan: Xiamen University
Xiaomin Shu: Xiamen University
Weisai Zu: Xiamen University
Zhong De: Xiamen University
Haohua Huo: Xiamen University

Nature Communications, 2021, vol. 12, issue 1, 1-8

Abstract: 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 in a nickel-catalyzed asymmetric acyl cross-coupling reaction. This bromine-radical-mediated C−H activation strategy can be also applied to the enantioselective coupling of alkylarenes with chloroformate for the synthesis of chiral α-aryl esters.

Date: 2021
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Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-23887-2

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DOI: 10.1038/s41467-021-23887-2

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