Trifunctionalization of Aryl Iodides with Two Distinct Nitrogen and Carbon Electrophiles by Palladium/Norbornene Catalysis
Jing Wang, Hui Wang, Zihan Wang, Linqiang Li, Qin Cheng, Xinjun Luan
Abstract
Main observation and conclusion Herein, we report a highly chemo‐ and regioselective vicinal trifunctionalization of aryl iodides by palladium/norbornene (Pd/NBE) catalysis. The key feature of this new method is the introduction of two distinct nitrogen and carbon electrophiles, with a large gap in reactivity, for ortho ‐unsubstituted aryl iodides via an intermolecular and intramolecular C―H functionalization, respectively. Eight types of ipso terminations can be coupled with both ortho ‐amination and ortho ‐alkylation, affording a variety of polysubstituted benzoheterocyclic scaffolds. Silicon‐tethered substrates can lead to polyfucntional arenes via a single‐step operation. Noteworthy, these products exhibit full‐color‐tunable strong fluorescence emissions with large Stokes shifts, and product 7r can serve as a fluorescent probe to specifically target lysosome in living cells.