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First Partially Intramolecular Palladium‐Catalyzed [2+2+2] Cycloaddition of Benzyne: Application to the Synthesis of Benzo[ b ]fluorenones
Author(s) -
Peña Diego,
Pérez Dolores,
Guitián Enrique,
Castedo Luis
Publication year - 2003
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.200390178
Subject(s) - aryne , chemistry , intramolecular force , regioselectivity , cycloaddition , palladium , steric effects , catalysis , medicinal chemistry , stereochemistry , computational chemistry , combinatorial chemistry , organic chemistry
The palladium(0)‐catalyzed reaction of benzyne with suitably functionalized benzodiynes to afford benzo[ b ]fluorenones is described. The outcome of the reaction is affected by the steric and electronic properties of the diynes and proved to be regioselective when an unsymmetrically substituted aryne is used. This work represents the first example of a partially intramolecular [2+2+2] cycloaddition involving arynes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)