Organic Photoredox Catalytic α-C(sp3)–H Phosphorylation of Saturated Aza-Heterocycles
Ming-Jun Yi,‡ Teng-Fei Xiao,‡ Wen-Hui Li, Yi-Fan Zhang, Pen-Ji Yan, Baoxin Zhang, Peng-Fei Xu and Guo-Qiang Xu
https://doi.org/10.1039/D1CC05767G
Abstract
A metal-free C(sp3)–H phosphorylation of saturated aza-heterocycles via the merger of organic photoredox and Brønsted acid catalysis was established under mild conditions. This protocol provided a straightforward and economic access to a variety of valuable α-phosphoryl cyclic amines by using commercially available diarylphosphine oxide reagents. In addition, the D-A fluorescent molecule DCQ was firstly used as a photocatalyst and exhibited excellent photoredox catalytic efficiency in this transformation. A series of mechanistic experiments and DFT calculations demonstrated that this transformation underwent a sequential visible-light photoredox catalytic oxidation/nucleophilic addition process.