Synlett 2024; 35(03): 357-361
DOI: 10.1055/a-2117-9803
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Organic Chemistry Under Visible Light: Photolytic and Photocatalytic Organic Transformations

Effects of Electron-Donor and Counter-Cation in Photoinduced Deboronative and Decarboxylative Aryl Radical Generation Using Two-Molecule Photoredox Catalysts

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This work was supported by the Asahi Glass Foundation, Continuation Grants for Outstanding Projects.


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Abstract

In this study, we investigated the effects of electron-donors and counter-cations on the visible-light-induced deboronation and decarboxylation of arylboronic acid derivatives and benzoic acids using two-molecule photoredox catalysts. Different efficiencies in aryl radical generation were observed upon replacing the electron-donor and counter-cation. The rate of photoinduced deboronation of arylboronic acid derivatives strongly depends on the substituent, whereas the influence of counter-cation (Na+ and K+) was relatively minor. In the case of the benzoate ion derived from benzoic acid, the effect of both substituent and counter-cation decreases because of the complex mechanism. Additionally, the dependence of the oxidation ability of the radical cation on the electron-donor suggests the possibility of roughly estimating the oxidation potentials of the arylborate and benzoate ions.

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Publication History

Received: 31 May 2023

Accepted after revision: 26 June 2023

Accepted Manuscript online:
26 June 2023

Article published online:
17 August 2023

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