Synthesis of 8,12-Dibromocorrole and Its Transformation to Antiaromatic 8,10-Fused Iminoisocorrole with a Polarized Resonance Contribution |
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Authors: | Dr. Kento Ueta Akito Nakai Dr. Takayuki Tanaka Prof. Dr. Atsuhiro Osuka |
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Affiliation: | Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan |
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Abstract: | 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 MnO2 afforded 8,10-fused iminoisocorrole in good yields. The iminoisocorrole exhibited weak antiaromaticity due to the C(+)−N(−) polarized resonance contribution as evidenced by 1H NMR spectrum, UV/vis absorption spectra, cyclic voltammetry, and theoretical calculations. |
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Keywords: | corrole isocorrole Suzuki coupling antiaromaticity cyclic voltammetry |
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