Defluorinative Diazolation-Cyclization Relay for Synthesis of Furan-Bridged Triheterocycles and Colorimetric Sensor Application

Abstract

Polyaromatics, as the assembly of diverse cyclic π-systems, exhibit unique physicochemical properties when compared to their individual constituents. In this study, we developed a strategic connection of two azacycles via a furan bridge through a defluorinative diazolation-cyclization reaction of trifluoromethyl enones and N-heterocycles. A range of modular 2,4-furan-bridged triheterocycles (FBTHs), featuring a C3-trifluoromethyl group, was synthesized with broad substrate scope and good regioselectivity under transition metal-free conditions. This three-component protocol was achieved through successive C(sp³)-F bond functionalization of one trifluoromethyl group, which is recognized for its stability and durability. Moreover, the synthetically useful functionalities such as bromide and formyl group could be easily installed on the resulting products, and the imidazole-containing FBTH could serve as a valuable ligand in the preparation of an advanced colorimetric sensor, thereby underscoring their potential applications.