A deoxyfluoroalkylation–aromatization strategy to access fluoroalkyl arenes

Abstract

Fluoroalkyl arenes (Ar–R_F) 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–R_F compounds benefit these applied fields. Herein, we report a deoxyfluoroalkylation–aromatization strategy to convert cyclohexanones into broad-spectrum Ar–R_F 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–R_F 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.