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Electrochemical Benzylic C(sp³)-H Acyloxylation.

ABSTRACT: The development of sustainable C(sp³)-H functionalization methods is of great interest to the pharmaceutical and agrochemical industries. Anodic oxidation is an efficient means of producing benzylic cations that can undergo subsequent in situ nucleophilic attack to afford functionalized benzylic products. Herein, we demonstrate the suitability of carboxylic acids as nucleophiles to yield benzylic esters. This method employs a series of secondary benzylic substrates and functionalized carboxylic acids and is demonstrated on a gram scale in flow.

SUBMITTER: Atkins AP

PROVIDER: S-EPMC9315976 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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Electrochemical Benzylic C(sp3)-H Acyloxylation.

Atkins Alexander P AP Rowett Albert C AC Heard David M DM Tate Joseph A JA Lennox Alastair J J AJJ

Organic letters 20220713 28

The development of sustainable C(sp3)-H functionalization methods is of great interest to the pharmaceutical and agrochemical industries. Anodic oxidation is an efficient means of producing benzylic cations that can undergo subsequent in situ nucleophilic attack to afford functionalized benzylic products. Herein, we demonstrate the suitability of carboxylic acids as nucleophiles to yield benzylic esters. This method employs a series of secondary benzylic substrates and function ...[more]

PMID: 35829756

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