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Palladium(0)/Copper(I)‐Catalyzed Tandem Cyclization of Aryl 1‐Cyanoalk‐5‐ynyl Ketone System: Rapid Assembly of Cyclopenta[ b ]naphthalene and Benzo[ b ]fluorene Derivatives
Author(s) -
Wong YingChieh,
Kao TzuTing,
Yeh YuCheng,
Hsieh BingSiou,
Shia KakShan
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300107
Subject(s) - chemistry , sonogashira coupling , palladium , fluorene , aryl , intramolecular force , ketone , naphthalene , catalysis , tandem , copper , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl , materials science , composite material , polymer
We have developed a new and general approach to construct a variety of benzo[ b ]fluorene and cyclopenta‐[ b ]naphthalene derivatives via the palladium(0)/copper(I)‐catalyzed tandem cyclization of aryl 1‐cyanoalk‐5‐ynyl ketone systems in an extremely efficient manner. The key operation lies in the copper(I)‐catalyzed aerobic oxidation, which allows for activation of two successive intramolecular cycloadditions immediately after the Sonogashira coupling reaction has occurred.