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Synthesis
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∗
This work has been supported financially in part by the Japan Science and Technology Corporation (JST CREST: JPMJCR18R4) and the Japan Society for the Promotion of Science (Grant-in-Aids for Scientific Research (B): 19H02728 to E.S.).
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Dedicated to Prof. Dennis P. Curran on the occasion of his 70th 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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2273-2895.
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Publication History

Received: 23 January 2024

Accepted after revision: 21 February 2024

Accepted Manuscript online:
21 February 2024

Article published online:
12 March 2024

© 2024. Thieme. All rights reserved

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