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Enhancing Reactivity and Selectivity of Aryl Bromides: A Complementary Approach to Dibenzo[ b,f ]azepine Derivatives
Author(s) -
Casnati Alessandra,
Fontana Marco,
Coruzzi Giovanni,
Aresta Brunella Maria,
Corriero Nicola,
Maggi Raimondo,
Maestri Giovanni,
Motti Elena,
Della Ca' Nicola
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201800940
Subject(s) - chemistry , azepine , aryl , selectivity , norbornene , medicinal chemistry , norbornadiene , iodide , catalysis , palladium , organic chemistry , combinatorial chemistry , alkyl , polymer , monomer
Dihydrodibenzo[ b , f ]azepines and dibenzo[ b , f ]azepines can be efficiently synthesized from aryl bromides, o ‐bromoanilines and norbornene or norbornadiene by means of palladium catalysis. This protocol gives access to dibenzo[ b , f ]azepine core containing a variety of electron‐withdrawing substituents on both aromatic rings and complements the previously reported methodology where electron rich aryl iodides were preferentially used. The presence of KI, even in sub‐stoichiometric amount, is crucial for this three‐component reaction. The proper addition of iodide anions has a dramatic effect on reaction rate and selectivity. A formal three‐step synthesis of the tricyclic antidepressant Clomipramine (Anafranil ® ) is also described.