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Paper | Regular issue | Vol 104, No. 6, 2022, pp.1059-1073
Published online, 22nd March, 2022
DOI: 10.3987/COM-22-14642
Access to Functionalized Pyrrolophenanthridine via an ortho C-H Amination/Interannular C-H Arylation Cascade of N-Arylpyrroles

Jitan Zhang,* Yuhang Li, Pengpeng Sun, Yue Zhang, Meihua Xie,* and Jiaping Wu*

*College of Chemistry and Materials Science, Anhui Normal University, 189 Jiuhua Nan Road, Wuhu, Anhui, 241002, China


An expeditious access to pyrrolophenanthridine scaffold enabled by a Catellani strategy from N-arylpyrroles and O-benzoylhydroxylamines is disclosed. This reaction proceeds smoothly involving an ortho C-H amination/interannular C-H arylation cascade and well tolerates a number of pyrrole and amine substrates. Furthermore, the potential of this protocol has been highlighted by the easily accessible scale-up synthesis and a plausible mechanism of this reaction was also proposed.