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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.