N-Arylation of DABCO with Diaryliodonium Salts: General Synthesis of N-Aryl-DABCO Salts as Precursors for 1,4-Disubstituted Piperazines.

Abstract

Employing DABCO as a substrate, aryl(mesityl)iodonium triflates are introduced as arylating agents for a tertiary sp3-nitrogen. Mild conditions and exceptional selectivity of the aryl group transfer allow unprecedented N-aryl-DABCO salts to be obtained, bearing substituents of different electronic natures. This metal-free methodology has no analogy among known transition-metal-based reactions. The utility of isolated N-aryl-DABCO salts is demonstrated for the preparation of flibanserin.