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Cascade Reactions of Aromatic Aldehydes with Electron‐Deficient Acetylenes: Regioselective Construction of Diverse Aromatic Ring Systems
Author(s) -
Cui SunLiang,
Lin XuFeng,
Wang YanGuang
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600560
Subject(s) - regioselectivity , chemistry , phenanthrenes , conjugated system , yield (engineering) , ring (chemistry) , triethylamine , cascade reaction , organic chemistry , aromaticity , cascade , combinatorial chemistry , photochemistry , catalysis , phenanthrene , molecule , materials science , metallurgy , polymer , chromatography
A new triethylamine‐catalyzed cascade reaction of aromatic aldehydes with terminal conjugated acetylenes has been developed. This serial multiple bond forming process furnishes diverse polycyclic aromatic hydrocarbons including naphthalenes, phenanthrenes, benzofurans, and tetrahydronaphtho[2,3‐ b ]furans. The chemical outcome of the process depends on the reaction temperature and can therefore be tailored selectively by an appropriate choice of experimental conditions. The resulting tetrahydronaphthofurans can be aromatized further to give strongly fluorescent naphtho[2,3‐ b ]furans (fluorescent quantum yield, Φ f , up to 0.94) in a one‐pot procedure. Furthermore, polysubstituted furans are obtained when the reaction is performed in the presence of dialkyl acetylenedicarboxylates. These cascade processes exhibit high bond‐forming efficiency and high regioselectivity.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)