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Structure and Reactivity of Aromatic Radical Cations Generated by FeCl₃

Author:
Horibe, Takahiro, Ohmura, Shuhei, Ishihara, Kazuaki
Source:
Journal of the American Chemical Society 2019 v.141 no.5 pp. 1877-1881
ISSN:
1520-5126
Subject:
X-ray diffraction, cations, cycloaddition reactions, ferric chloride
Abstract:
This paper describes the isolation and characterization of an aromatic radical cation generated by FeCl₃. 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 FeCl₄– is observed. Leveraging the efficient generation of the radical cation–FeCl₄– ion pair, we explore a radical cation-induced cycloaddition of trans-anethole initiated by catalytic amount of FeCl₃. 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 FeCl₃ as a simple and a highly active initiator.
Agid:
6302566