Synthesis of Arylated Perylene Bisimides through C−H Bond Cleavage under Ruthenium Catalysis

Synthesis of Arylated Perylene Bisimides through C−H Bond Cleavage under Ruthenium Catalysis

Treatment of perylene bisimide (PBI) with various arylboronates in the presence of a ruthenium catalyst provides tetraarylated PBIs at 2,5,8,11-positions in good yields with perfect regioselectivity. The electronic nature of the introduced aryl substituents has a significant impact on their optical...

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Veröffentlicht in:Organic letters 2009-12, Vol.11 (23), p.5426-5429
Hauptverfasser: Nakazono, Satomi, Easwaramoorthi, Shanmugam, Kim, Dongho, Shinokubo, Hiroshi, Osuka, Atsuhiro
Format: Artikel
Sprache:eng
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Zusammenfassung:Treatment of perylene bisimide (PBI) with various arylboronates in the presence of a ruthenium catalyst provides tetraarylated PBIs at 2,5,8,11-positions in good yields with perfect regioselectivity. The electronic nature of the introduced aryl substituents has a significant impact on their optical and electronic properties. This protocol has been applied to the synthesis of a water-soluble emissive PBI derivative.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol902271b