Selective Arene Photonitration via Iron-Complex β-Homolysis
Shuyang Liu, Ziyu Gan, Min Jiang, Qian Liao, Yusheng Lu, Hongyao Wang, Zhiyan Xue, Ziyang Chen, Yongqiang Zhang, Xiaobo Yang, Chunying Duan, Yunhe Jin
Abstract
Nitroaromatics, as an important member and source of nitrogen-containing aromatics, is bringing enormous economic benefits in fields of pharmaceuticals, dyes, pesticides, functional materials, fertilizers, and explosives. Nonetheless, the notoriously polluting nitration industry, which suffers from excessive discharge of fumes and waste acids, poor functional group tolerance, and tremendous purification difficulty, renders mild, efficient, and environmentally friendly nitration a formidable challenge. Herein, we develop a visible-light-driven biocompatible arene C-H nitration strategy with good efficiency and regioselectivity, marvelous substrate applicability and functional group tolerance, and wide application in scale-up synthesis, total synthesis, and late-stage functionalization. A nitryl radical delivered through unusual β-homolysis of a photoexcited ferric-nitrate complex is proposed to be the key nitrification reagent in this system.