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PdCl 2 ‐Catalyzed Domino Reactions of 2‐Alkynylbenzaldehydes with Indoles: Synthesis of Fluorescent 5 H ‐Benzo[ b ]carbazol‐6‐yl Ketones
Author(s) -
Tang RiYuan,
Li JinHeng
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000133
Subject(s) - domino , indole test , chemistry , catalysis , fluorescence , carbazole , combinatorial chemistry , medicinal chemistry , photochemistry , organic chemistry , physics , quantum mechanics
Synthetic methods : A new, selective Pd‐catalyzed domino reaction of 2‐alkynylbenzaldehydes with indoles has been developed for the synthesis of 5 H ‐benzo[ b ]carbazol‐6‐yl ketones. The isobenzopyrylium complex is trapped by indole at room temperature to give 3‐(1 H ‐isochromen‐1‐yl)‐1 H ‐indoles, which can be transformed into 5 H ‐benzo[ b ]carbazol‐6‐yl ketones by raising the temperature (see scheme). These ketones exhibit intense fluorescence and interact with metal ions to enhance the fluorescence intensity.