期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 16, 期 16, 页码 2253-2256出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.202100577
关键词
corrole; isocorrole; Suzuki coupling; antiaromaticity; cyclic voltammetry
资金
- JSPS KAKENHI [JP20K05463, JP18H03910]
- JSPS Fellowships for Young Scientists
The 8,12-Dibromo-5,15-bis(pentafluorophenyl)corrole and its Ag(III) complex were prepared through intramolecular oxidative coupling, and further transformed via Suzuki coupling reaction to yield the 8,10-fused iminoisocorrole. The iminoisocorrole exhibited weak antiaromaticity due to the C(+)-N(-) polarized resonance contribution, as confirmed by various spectroscopic techniques and theoretical calculations.
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 beta-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 H-1 NMR spectrum, UV/vis absorption spectra, cyclic voltammetry, and theoretical calculations.
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