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Visible-Light-Induced N-Heterocyclic Carbene-Catalyzed Single Electron Reduction of Mono-Fluoroarenes
He Sheng1, Qiang Liu1, Bei-Bei Zhang1
1School of Chemical Sciences, University of the Chinese Academy of Sciences, Beijing, 100049, China.
Abstract:
Fluoroarenes are abundant and readily available feedstocks. However, due to the high reduction potentials of mono-fluoroarenes, their photoreduction remains a continuing challenge, motivating the development of efficient activation modes to address this issue. This report presents the blue light-induced N-heterocyclic carbene (NHC)-catalyzed single electron reduction of mono-fluoroarenes for biaryl cross-couplings. We discovered that under blue light irradiation, NHC/tBuOK combination could construct powerful photoactive architectures to promote single electron transfer for Caryl -F bond reduction via forming highly reducing NHC radical anion. Notably, the strategy was also successful to reduce Caryl -O, Caryl -N, and Caryl -S bonds for biaryl cross-couplings.
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