Organophotoredox-Catalyzed Umpolung Strategy to β‑Fluoroamides via Carbamoylative Fluorination of Alkene in Aqueous Medium

The development of a visible-light-mediated
biocompatible reaction
under ambient aqueous conditions using a reactive traceless warhead
is an unmet need for the modification of biomolecules with exquisite
spatiotemporal control. Here we disclose bench-stable amino-acid-derived
oxamic acid as a carbamoyl radical progenitor for the three-component
vicinal carbamoylative fluorination of styrene derivatives as well
as unactivated alkenes under visible light irradiation in aqueous
or buffer medium, offering a unique opportunity for N-terminal modification of amino acids, peptides and biomolecules.