Enhancing Reactivity and Selectivity of Aryl Bromides: A Complementary Approach to Dibenzo[b,f]azepine Derivatives

Autor: Elena Motti, Marco Fontana, Giovanni Maestri, Raimondo Maggi, Alessandra Casnati, Nicola Della Ca, Nicola Corriero, Brunella Maria Aresta, Giovanni Coruzzi
Jazyk: angličtina
Rok vydání: 2018
Předmět:
Zdroj: ChemCatChem
info:cnr-pdr/source/autori:Casnati, Alessandra; Fontana, Marco; Coruzzi, Giovanni; Aresta, Brunella Maria; Corriero, Nicola; Maggi, Raimondo; Maestri, Giovanni; Motti, Elena; Della Ca', Nicola/titolo:Enhancing Reactivity and Selectivity of Aryl Bromides: A Complementary Approach to Dibenzo[b,f]azepine Derivatives/doi:10.1002%2Fcctc.201800940/rivista:ChemCatChem (Print)/anno:2018/pagina_da:4346/pagina_a:4352/intervallo_pagine:4346–4352/volume:10
DOI: 10.1002/cctc.201800940
Popis: 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 (R)) is also described.
Databáze: OpenAIRE