Organic photoredox catalytic α-C(sp 3 )-H phosphorylation of saturated aza -heterocycles

A metal-free C(sp )-H phosphorylation of saturated -heterocycles the merger of organic photoredox and Brønsted acid catalyses was established under mild conditions. This protocol provided straightforward and economic access to a variety of valuable α-phosphoryl cyclic amines by using commercially av...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2021-12, Vol.57 (97), p.13158-13161
Hauptverfasser: Yi, Ming-Jun, Xiao, Teng-Fei, Li, Wen-Hui, Zhang, Yi-Fan, Yan, Pen-Ji, Zhang, Baoxin, Xu, Peng-Fei, Xu, Guo-Qiang
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Sprache:eng
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Zusammenfassung:A metal-free C(sp )-H phosphorylation of saturated -heterocycles the merger of organic photoredox and Brønsted acid catalyses was established under mild conditions. This protocol provided 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 used for the first time as a photocatalyst and exhibited an 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.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc05767g