55. A Deoxyfluoroalkylation-Aromatization Strategy to Access Fluoroalkyl Arenes

Bhattarai, P.; Koley, S. K.; Goel, K.; Altman, R. A.*

Chem. Commun. 2025, Manuscript Accepted.

Fluoroalkyl arenes (Ar–RF) are valuable substructures present in several FDA-approved drugs, patents, agrochemicals, and materials, and complementary strategies that enable access to a broad spectrum of Ar–RF compounds benefit these applied fields. Herein, we report a deoxyfluoroalkylation-aromatization strategy to convert cyclohexanones into a broad-spectrum Ar–RF containing compounds. Generally, the fluoroalkyl sources were activated to participate in a 1,2-addition reaction followed by aromatization in a sequence that contrasts more common preparations of these Ar–RF compounds, such as i) transition-metal catalyzed cross-coupling reactions of aryl electrophiles and nucleophiles, and ii) radical fluoroalkylation reactions of C–H bonds of arenes. Considering the range of cyclohexanone-derived substrates that could be prepared and used, this strategy can be creatively employed to deliver a broad spectrum of highly substituted fluoroalkyl arenes.