Synthesis of N-Fused Polycyclic Indole Derivatives via Ru(II)-Catalyzed C-H Bond Activation and Intramolecular Hydroarylation.

Abstract

A new synthesis of N-fused tetracyclic indole derivatives and their related polycyclic analogues has been developed based on ruthenium(II)-catalyzed C-H activation and intramolecular hydroarylation. A series of polycyclic indoles with a 3-formyl group have been prepared in good to high yields. Various aliphatic and aromatic amines have been studied to form a transient directing group with the aldehyde for the catalytic process. A significant impact of the structures of the aromatic amines was identified, and 1-naphthylamine was shown to enable the catalytic process. DFT computations were performed to gain further insight into the role of the transient directing groups.