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Palladium‐Catalyzed Reaction of Aryl Iodides with ortho ‐Bromoanilines and Norbornene/Norbornadiene: Unexpected Formation of Dibenzoazepine Derivatives
Author(s) -
Della Ca' Nicola,
Maestri Giovanni,
Malacria Max,
Derat Etienne,
Catellani Marta
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201104363
Subject(s) - norbornadiene , norbornene , aryl , catalysis , palladium , iodide , chemistry , medicinal chemistry , organic chemistry , combinatorial chemistry , alkyl , monomer , polymer
Expecting the unexpected : The title reaction leads to satisfactory yields of dihydrodibenzoazepines 1 a from norbornene. The dibenzoazepines 2 can also be accessed from compounds of type 1 b when norbornadiene is used as a reactant. Theoretical studies show that the reaction represents a chelation‐driven deviation from the usual selectivity observed in the presence of ortho ‐substituents on the aryl iodide.