Dirhodium-catalyzed one-step cascade intermolecular 1,4-diamination via cyclopropanation

Abstract

This work presents a novel dirhodium-catalyzed method for the conversion of aromatic hydrocarbons to 1,4-diamines using N-fluorobenzenesulfonimide (NFSI) as the nitrogen source. It is characterized by the activation of inert secondary and primary C(sp³)–H bonds under mild conditions to yield 1,4-diaminated products. The methodology involves arylcyclopropane intermediates, as suggested by density functional theory (DFT) calculations. This approach not only simplifies the multifunctionalization of carbon frameworks, but also demonstrates the efficacy of the dirhodouim catalyst. It opens up new possibilities for C(sp³)–H to C(sp³)–N bond transformations, laying the groundwork for future developments in complex molecule synthesis.