Photoredox-catalyzed three-component radical coupling of potassium alkyltrifluoroborates, DABSO and polyfluoroarenes

Abstract

Polyfluoroarylsulfones not only exhibit distinctive biological and pharmacological activities but also serve as versatile building blocks in organic synthesis, functional materials, polymer photosensitizers, etc. The direct incorporation of the polyfluoroaryl sulfonyl moiety into organic compounds remains an unexplored yet intriguing challenge. In this study, we present a visible light-driven three-component coupling of RBF₄K, DABSO reagent, and polyfluoroarenes through radical–polar crossover mechanisms. Interestingly, this methodology achieves direct C(sp²)–F bond cleavage of polyfluoroarenes under mild conditions, establishing DABSO/polyfluoroarenes as unprecedented polyfluoroarylsulfonation reagents. The synergistic integration of the high reactivity of radical species with the precise regioselectivity of S_NAr processes constitutes the foundation of this innovative strategy. This approach provides a modular platform for synthesis of polyfluoroarylsulfones.