Low-Energy Photocatalytic C-H Amination of Arenes Enabled by an Orange-Light Organic Photooxidant.

Direct C-H amination of arenes provides rapid access to C-N bonds in pharmaceuticals, agrochemicals, and functional materials, yet most photoredox approaches require high-energy blue light. Here, we introduce a low-energy orange-light photoredox platform for aryl C-H amination using a fluorinated azadioxotriangulenium (2FADOTA+) photocatalyst (λmax = 555 nm, E*red = 1.85 V vs SCE). This system enables efficient C-H amination of electron-rich arenes, heteroarenes, and sterically demanding scaffolds with both azole and aliphatic amines, including amino acid esters. Late-stage functionalization of medicinally relevant molecules is achieved under mild conditions, demonstrating broad applicability. Mechanistic studies support arene oxidation as the productive pathway. This work establishes 2FADOTA+ as a low-energy photooxidant platform capable of accessing strongly oxidizing reactivity under orange-light irradiation, expanding the accessible photoredox landscape beyond conventional blue-light systems.