A General Platform for the Light‐Enabled Generation of α‐Fluoro Radicals Leveraging Simple Additives
Year: 2025
Type: article
Abstract: ABSTRACT The strategic generation of α‐fluoro radicals underpins powerful routes to fluorine‐rich architectures of high value in molecular design. Here, we disclose an operationally simple, catalyst‐free method for the photochemical activation of α‐halo fluorinated precursors using visible light and two inexpensive additives, sodium iodide and 2,6‐lutidine. This mild protocol enables in‐situ halide exchange and subsequent homolytic C–I bond scission to generate α‐fluoro radicals under ambient conditions. The generality of the platform is demonstrated across esters, sulphones, and nitriles, facilitating intermolecular coupling with alkenes, heteroarenes, and propellanes to access diverse fluorinated scaffolds. Mechanistic studies support the formation of a weak electron donor–acceptor complex that mediates bond activation, while the benign conditions permit merger with energy transfer catalysis for stereodivergent product formation.
Source: Helvetica Chimica Acta
Authors: Jonas Klagge, Maria Mazhuga, John J. Molloy
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,030
OpenAlex ID: W7117368090