Palladium-Catalyzed C(sp3)-H Biarylation of 8-Methyl Quinolines with Cyclic Diaryliodonium Salts to Access Functionalized Biaryls and Fluorene Derivatives

Herein, we have developed the cyclic diaryliodonium salts as biarylating agents in the C(sp3)-H functionalization using 8-methyl quinoline as the intrinsic directing group. The oxidant-free reaction produces a vast array of the biarylated products with iodo functionality that can be further functionalized. Additionally, intramolecular C(sp3)-H functionalization in a stepwise manner under palladium-catalyzed conditions produced the fluorene derivatives in excellent yields.

Automated summary

In this study, cyclic diaryliodonium salts were developed as biarylating agents for C(sp3)-H functionalization, using 8-methyl quinoline as the intrinsic directing group. The oxidant-free reaction resulted in a wide range of biarylated products with iodo functionality, which can be further functionalized. Furthermore, intramolecular C(sp3)-H functionalization under palladium-catalyzed conditions produced fluorene derivatives with excellent yields.