Abstract
Visible light-driven carboxylation with CO 2 have emerged as a sustainable and powerful way to transfer waste to treasure. However, it is still challenging for aryl fluorides due to the low reactivities of both C( sp 2 )−F bonds and CO 2 . Herein, we report the first photocatalytic carboxylation of aryl C−F bonds with CO 2 . The visible-light photoredox catalysis enables selective carboxylation of strong C( sp 2 )−F bonds in diverse polyfluoroarenes, such as penta-, tetra-, and tri-fluoroarenes under mild conditions, providing a facile access to a series of important polyfluoroaryl carboxylic acids with good yields. In contrast to previous reports of direct capture of polyfluoroaryl radicals, mechanistic studies suggest that the reduction of fleeting polyfluoroaryl radicals into polyfluoroaryl anions might be involved in this transformation, which may open a new avenue for photocatalytic functionalization of aryl C−F bonds. Visible-light photoredox-catalyzed selective carboxylation of C( sp 2 )−F bonds in polyfluoroarenes with CO 2 is developed under mild reaction conditions involving polyfluoroaryl anions as the possible key intermediates, which may provide a new strategy for photocatalytic transformations of aryl C( sp 2 )−F bonds.
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