Anion-driven C[sbnd]F bond cleavage of trifluoromethyl N-aryl hydrazones toward the assembly of N-heterocycles

Abstract

Herein we report an efficient and convenient method for synthesizing 1H-benzo[d]imidazoles via a base-promoted reaction of readily available α-CF3 ketone-derived hydrazones with o-phenylenediamines. The key innovation is the anion-driven triple-cleavage of the CF bond in the CF3 group, which acts as a C1 synthon at the 2-position of the 1H-benzo[d]imidazole. This novel approach simplifies the synthesis and can be extended to the preparation of benzo[d]oxazoles and benzo[d]thiazoles. Our method offers a versatile and robust platform for the synthesis of important heterocyclic compounds, with potential applications in medicinal chemistry and drug discovery.