Regioselective Nucleophilic Functionalization of Antiaromatic Nickel(II) Norcorroles |
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Authors: | Ryo Nozawa Keitaro Yamamoto Prof?Dr Ji‐Young Shin Prof?Dr Satoru Hiroto Prof?Dr Hiroshi Shinokubo |
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Institution: | Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Aichi, 464‐8603 (Japan) |
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Abstract: | Treatment of antiaromatic nickel(II) norcorrole with potassium cyanide provided nickel(II) 3‐cyanonorcorrole with perfect regioselectivity without the help of a catalyst. The reaction of the nickel(II) norcorrole with phenol or thiophenol in the presence of a base also yielded substitution products. The antiaromatic 16π conjugation system in the norcorrole core was preserved in the functionalized products. Introduction of phenylthio groups significantly decreased the HOMO–LUMO gap and enhanced the near IR absorption property. |
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Keywords: | aromaticity electrophilic substitution nickel porphyrinoids X‐ray diffraction |
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