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

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.

Key words

two-molecule photoredox catalyst - effect of electron-donor - effect of counter-cation - photoinduced deboronation - photoinduced decarboxylation - aryl radical - arylboronic acid ester - benzoic acid

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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