Merging Copper(I) Photoredox Catalysis and Iodine(III) Chemistry for the Oxy-monofluoromethylation of Alkenes

Angewandte Chemie International Edition 2023
Nagarajan Ramkumar, Larisa Baumane, Dzintars Zacs, Jānis Veliks

A simple process for the oxy-monofluoromethylation of alkenes is described. In combination with visible-light copper(I) photoredox catalysis, an easily accessible iodine(III) reagent containing monofluoroacetoxy ligands serves as a powerful source of a monofluoromethyl (CH2F) radical, enabling the step economical synthesis of γ-fluoro-acetates from a broad range of olefinic substrates under mild conditions. Applications to late-stage diversification of alkenes derived from complex molecules, amino acids and the synthesis of fluoromethylated heterocycles are also demonstrated.

Keywords
Copper | Hypervalent Iodine | Monofluoromethylation | Photoredox Catalysis | Radicals
DOI
10.1002/anie.202219027
Hyperlink
https://onlinelibrary.wiley.com/doi/10.1002/anie.202219027

Ramkumar, N., Baumane, L., Zacs, D., Veliks, J. Merging Copper(I) Photoredox Catalysis and Iodine(III) Chemistry for the Oxy-monofluoromethylation of Alkenes. Angewandte Chemie International Edition, 2023, Vol. 62, No. 12, Article number e202219027. ISSN 1433-7851. e-ISSN 1521-3773. Available from: doi:10.1002/anie.202219027

Publication language
English (en)