Synthesis of 1-Substituted 2-(Trifluoromethyl)indoles via a Palladium-Catalyzed Double Amination Reaction

Abstract

A new, selective protocol for the synthesis of 1-substituted 2-(trifluoromethyl)indoles has been developed by palladium-catalyzed double amination reaction of 2-chloro-1-(2-halophenyl)-3,3,3-trifluoroprop-1-enes with primary amines. This route allows the formation of two C-N bonds in one pot from the reaction between 2-chloro-1-(2-halophenyl)-3,3,3-trifluoroprop-1-enes and primary amines using the Pd 2 (dba) 3 /L4/t-BuONa system.

Synthesis of Trifluoromethylated Dibenzoxepines via Palladium-Catalyzed Tandem C–O Bond Formation/C–H Arylation

“…Recently, palladium-catalyzed annulation reactions have drawn tremendous attention because of the powerful catalytic activity of palladium catalysts in both C–H and C–X functionalization . In addition, the easily prepared trifluoromethyl-containing ortho -bromo-β-chlorostyrenes have been becoming useful building blocks for accessing various trifluoromethylated heterocyclics . We envisioned that trifluoromethyl-incorporated dibenzoxepines could be prepared from the intermolecular C–O coupling reaction of phenols with alkenyl chlorides and the subsequent C–H bond arylation with aryl bromides.…”