Structure and Reactivity of Aromatic Radical Cations Generated by FeCl3

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This paper describes the isolation and characterization of an aromatic radical cation generated by FeCl 3 . X-ray crystallographic analysis and kinetic studies reveal the mechanism of the generation of aromatic radical cation. In the solid state, a tight ion-pair of a radical cation with FeCl 4 – is observed. Leveraging the efficient generation of the radical cation–FeCl 4 – ion pair, we explore a radical cation-induced cycloaddition of trans -anethole initiated by catalytic amount of FeCl 3 . Both [4+2] cycloaddition and [2+2] cycloaddition with a broad substrate scope are also described. Moreover, a 100 g-scale reaction is demonstrated with the use of 1 mol % of FeCl 3 as a simple and a highly active initiator.