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Enhancing Reactivity and Selectivity of Aryl Bromides: A Complementary Approach to Dibenzo[b,f]azepine Derivatives
ChemCatChem ( IF 4.5 ) Pub Date : 2018-08-07 , DOI: 10.1002/cctc.201800940
Alessandra Casnati 1 , Marco Fontana 1 , Giovanni Coruzzi 1 , Brunella Maria Aresta 2 , Nicola Corriero 2 , Raimondo Maggi 1 , Giovanni Maestri 1 , Elena Motti 1 , Nicola Della Ca' 1
Affiliation  

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.

中文翻译:

增强芳基溴化物的反应性和选择性:二苯并[b,f]氮杂环庚烷衍生物的一种补充方法

二氢二苯并[ bf ]氮杂和二苯并[ bf ]氮杂可以通过钯催化从芳基溴化物,溴代苯胺和降冰片烯或降冰片二烯有效合成。该协议可以访问二苯并[ bf]氮杂core核在两个芳环上均包含多个吸电子取代基,并补充了先前报道的方法,在该方法中优先使用富含电子的芳基碘化物。KI的存在,即使是低于化学计量的量,对于该三组分反应也至关重要。适当添加碘化物阴离子对反应速率和选择性具有显着影响。的三环类抗抑郁药氯米帕明(安那芬尼正式三步合成®)也被描述。
更新日期:2018-08-07
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