Trifunctionalization of aryl iodides via intermolecular C-H acylation/intramolecular C-H alkylation achieved using palladium/norbornene cooperative catalysis

Herein, we describe a palladium/norbornene-catalyzed trifunctionalization of ortho-unsubstituted aryl iodides via a highly chemoselective cascade process involving intermolecular ortho acylation/intramolecular ortho alkylation/ipso alkenylation. This approach was shown to provide a modular and efficient strategy for preparing a variety of polyfunctional benzoheterocyclic scaffolds. Initial success on ipso cyanation was also achieved by using CuCN as the terminal reagent. In addition, the resulting products could be further transformed to various interesting polycyclic compounds.

Automated summary

This article describes a palladium/norbornene-catalyzed trifunctionalization of ortho-unsubstituted aryl iodides via a highly chemoselective cascade process involving intermolecular ortho acylation/intramolecular ortho alkylation/ipso alkenylation. This approach provides a modular and efficient strategy for preparing various polyfunctional benzoheterocyclic scaffolds.