Photo-Induced α-Oxyalkylation of Aryl Chlorides with Ethers and Alcohols through Homolytic Aromatic Substitution

Kohei Aoki; Kyohei Yonekura; Wataru Ejima; Shota Tanaka; Ami Shigeta; Eiji Shirakawa

doi:10.1055/a-2273-2895

Synthesis, Table of Contents

Synthesis 2024; 56(21): 3314-3326
DOI: 10.1055/a-2273-2895

paper

Special Issue PSRC-10 (10th Pacific Symposium on Radical Chemistry)

Photo-Induced α-Oxyalkylation of Aryl Chlorides with Ethers and Alcohols through Homolytic Aromatic Substitution

Kohei Aoki

,

Kyohei Yonekura

,

Wataru Ejima

,

Shota Tanaka

,

Ami Shigeta

,

Eiji Shirakawa∗

Abstract

All articles of this category

Dedicated to Prof. Dennis P. Curran on the occasion of his 70^th birthday

Abstract

The α-oxyalkylation of aryl chlorides with ethers and alcohols using a small amount of a peroxide was found to be induced by photoirradiation. The reaction proceeds through a homolytic aromatic substitution (HAS) mechanism consisting of addition of an α-oxyalkyl radical to an aryl chloride and elimination of the chlorine atom to give the α-oxyalkylation product, where photoirradiation is considered to effect not only the initiation step to facilitate homolysis of a peroxide, but also the propagating radical chain.

Key words

aromatic substitution - photoirradiation - radical reactions - reaction mechanism - synthetic methods

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References

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