Preparation of α-Perfluoroalkyl Ketones from α,β-Unsaturated Ketones via Formal Hydroperfluoroalkylation

Formal hydroperfluoroalkylation of enones is achieved in a two-step process comprising conjugate hydroboration and subsequent radical perfluoroalkylation. The 1,4-hydroboration of the enone is conducted in the absence of any transition metal catalyst with catecholborane in 1,2-dichloroethane, and the generated boron enolate is in situ alpha-perfluoroalkylated with a perfluoroalkyl iodide upon blue LED irradiation in the presence of an amine additive. Both reactions proceed under very mild conditions at room temperature.

Automated summary

Formal hydroperfluoroalkylation of enones is achieved through a two-step process involving conjugate hydroboration and subsequent radical perfluoroalkylation. Both reactions proceed under very mild conditions at room temperature, making the process convenient and efficient.