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: |
010405 organic chemistry
Aryl Organic Chemistry chemistry.chemical_element 010402 general chemistry palladium 01 natural sciences Medicinal chemistry Catalysis 0104 chemical sciences Inorganic Chemistry chemistry.chemical_compound C-H bond activation azepine chemistry iodide anions Reactivity (chemistry) Physical and Theoretical Chemistry Azepine Selectivity 7-membered ring Palladium |
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 |
Externí odkaz: |