Photoredox-Catalyzed Radical–Radical Coupling of Potassium Trifluoroborates with Acyl Azoliums

Abstract

Potassium trifluoroborates have gained significant utility as coupling partners in organic synthesis, particularly in the Suzuki–Miyaura coupling reaction. Recently, they have also been used as radical precursors under oxidative conditions to generate carbon-centered radicals. These versatile reagents have found new applications in photoredox catalysis, including radical substitution, conjugate-addition reactions, and transition-metal dual catalysis. In addition, this photomediated redox-neutral process has enabled radical–radical coupling with persistent radicals in the absence of a metal, and this process remains to be fully explored. In this study, we report the radical–radical coupling of potassium benzylic trifluoroborate salts with isolated acyl azolium triflates, which are persistent-radical precursors. The reaction is catalyzed by an organic photocatalyst and forms isolable tertiary alcohol species. These products can be transformed into a range of substituted ketone products by simple treatment with a mild base.

Key words

potassium trifluoroborate - photoredox catalysis - organophotocatalysis - acyl azolium compounds - radical–radical coupling - ketones

Publication History

Received: 04 May 2023

Accepted after revision: 14 June 2023

Article published online:
16 August 2023

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