Iridium-catalyzed direct tetraborylation of perylene bisimides |
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Authors: | Teraoka Takuro Hiroto Satoru Shinokubo Hiroshi |
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Institution: | Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya, Japan. |
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Abstract: | Treatment of perylene bisimides (PBIs) with bis(pinacolato)diboron in the presence of an iridium catalyst provides tetraborylated PBIs at 2,5,8,11-positions in good yields with perfect regioselectivity. The planar structure of the perylene core has been confirmed by X-ray diffraction analysis. Oxidation of tetraborylated PBI with hydroxylamine hydrochloride affords tetrahydroxy PBI in excellent yield, which exhibits a substantially blue-shifted absorption spectrum due to an intramolecular hydrogenbonding interaction between carbonyl and hydroxy groups. |
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