Near-infrared (NIR) light is highly attractive for photoreactions because of its stronger penetration capability, which is a great advantage for raising the efficiency and scalability of photoreac-tions. However, applications of NIR light to synthetic organic transformations remain underdeveloped due to its low energy. Herein, we describe an efficient NIR-light-induced halogen-atom transfer (XAT) process enabled by a bench-stable, commercially available, and cheap iron(I) dimer ([CpFe(CO)2]2). The XAT strategy enables iodoperfluoroalkylation of various alkenes, including pharmaceuti-cally relevant compounds. The method is distinguished by operational simplicity, short reaction time (<5 min), superior penetration, and excellent scalability (200 mmol). The experimental and computational studies suggested that [CpFe(CO)2]2 undergoes efficient Fe-Fe bond homolysis upon NIR-light irradiation, giving a metalloradical that is able to abstract iodide atoms from perfluor-oalkyl iodide for the generation of alkyl radicals.
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