Synthesis of 8,12‐Dibromocorrole and Its Transformation to Antiaromatic 8,10‐Fused Iminoisocorrole with a Polarized Resonance Contribution | Zendy

Ueta Kento | Zendy; Nakai Akito | Zendy; Tanaka Takayuki | Zendy; Osuka Atsuhiro | Zendy

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Synthesis of 8,12‐Dibromocorrole and Its Transformation to Antiaromatic 8,10‐Fused Iminoisocorrole with a Polarized Resonance Contribution

Author(s) -

Ueta Kento,

Nakai Akito,

Tanaka Takayuki,

Osuka Atsuhiro

Publication year - 2021

Publication title -

chemistry – an asian journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.18

H-Index - 106

eISSN - 1861-471X

pISSN - 1861-4728

DOI - 10.1002/asia.202100577

Subject(s) - antiaromaticity , intramolecular force , cyclic voltammetry , chemistry , resonance (particle physics) , corrole , photochemistry , oxidative coupling of methane , absorption spectroscopy , absorption (acoustics) , crystallography , stereochemistry , materials science , electrochemistry , organic chemistry , aromaticity , molecule , electrode , catalysis , physics , composite material , particle physics , quantum mechanics

8,12‐Dibromo‐5,15‐bis(pentafluorophenyl)corrole and its Ag(III) complex were prepared via intramolecular oxidative coupling of a 8,12‐dibromobilane precursor. The Ag(III) complex was allowed for further transformation via Suzuki coupling reaction. Thus, 2‐aminophenyl group was coupled at one of the β ‐positions, and subsequent demetalation followed by oxidation with MnO 2 afforded 8,10‐fused iminoisocorrole in good yields. The iminoisocorrole exhibited weak antiaromaticity due to the C(+)−N(−) polarized resonance contribution as evidenced by 1 H NMR spectrum, UV/vis absorption spectra, cyclic voltammetry, and theoretical calculations.

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