American Chemical Society
ol1c03526_si_001.pdf (11.65 MB)

Terminal Trifluoromethylation of Ketones via Selective C–C Cleavage of Cycloalkanols Enabled by Hypervalent Iodine Reagents

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journal contribution
posted on 2021-11-17, 16:03 authored by Shuang Wu, Junzhao Li, Ru He, Kunfang Jia, Yiyun Chen
We report the first terminal trifluoromethylation at aryl and alkyl ketones’ γ, δ, ε, or more remote sites via the selective C–C bond cleavage of cycloalkanols. The noncovalent interactions between alcohols and hypervalent iodines­(III) reagents were disclosed to activate both alcohols and the Togni I reagent in the dual photoredox/copper catalysis for the transformation. This reaction was scalable to the gram-scale synthesis, applicable to the structurally complex steroid trifluoromethylation, and extendable to the pentafluoroethylation.