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Preparation of ?-Perfluoroalkyl Ketones from ?,?-Unsaturated Ketones via Formal Hydroperfluoroalkylation.

ABSTRACT: 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 ?-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.

SUBMITTER: Jana K

PROVIDER: S-EPMC7901661 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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

Jana Kalipada K Mizota Isao I Studer Armido A

Organic letters 20210202 4

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 α-perfluoroalkylated with a perfluoroalkyl iodide upon blue LED irradiation in the presence of an amine additive. Both reactions proceed under very mild conditions ...[more]

PMID: 33530687

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