Trifunctionalization of Aryl Iodides with Two Distinct Nitrogen and Carbon Electrophiles by Palladium/Norbornene Catalysis

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.

Automated summary

This paper reports a highly chemoselective and regioselective vicinal trifunctionalization of aryl iodides using palladium/norbornene catalysis, introducing two distinct nitrogen and carbon electrophiles. The resulting products exhibit strong fluorescence emissions with full-color tunability, and product 7r can serve as a fluorescent probe specifically targeting lysosomes in living cells.