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

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

Publication History

Received: 23 January 2024

Accepted after revision: 21 February 2024

Accepted Manuscript online:
21 February 2024

Article published online:
12 March 2024

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