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Borane‐Catalyzed Hydrogenation of Tertiary Amides Activated by Oxalyl Chloride: DFT Mechanistic Insights
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2019-06-25 , DOI: 10.1002/ejoc.201900827
Hui Zhu 1 , Zheng-Wang Qu 1 , Stefan Grimme 1
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2019-06-25 , DOI: 10.1002/ejoc.201900827
Hui Zhu 1 , Zheng-Wang Qu 1 , Stefan Grimme 1
Affiliation
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Amide activation and hydrogenation: Fast electrophilic activation of tertiary amides by (COCl)2 is favoured by exergonic gas release, affording the separated chloroiminium and Cl– ions in chloroform. The B(2,6‐F2C6H3)3/Cl– frustrated Lewis pair may then cleave H2 over a barrier of 24.3 kcal/mol as rate‐limiting step, leading to transient hydridoborate for rapid hydride reduction of chloroiminium. A stepwise amide activation and reduction is suggested to realize milder reaction conditions and improved product yield.
中文翻译:
硼烷催化的草酰氯活化的叔酰胺加氢:DFT机理的见解
酰胺激活和氢化:由(氯化钴)叔酰胺的快速电活化2被放能释放气体的青睐,得到分离的氯代和Cl -在氯仿中的离子。的B(2,6-F 2 C ^ 6 ħ 3)3 /氯-沮丧路易斯一对可随后裂开ħ 2上的24.3阻挡千卡/摩尔作为限速步骤,导致瞬时化硼酸快速氢化物还原氯代的。建议逐步进行酰胺活化和还原,以实现较温和的反应条件并提高产物收率。
更新日期:2019-06-25
![image image](https://wol-prod-cdn.literatumonline.com/cms/attachment/9cbc6676-c623-482e-aa12-9a97edcb7d3d/ejoc201900827-toc-0001-m.png)
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
硼烷催化的草酰氯活化的叔酰胺加氢:DFT机理的见解
酰胺激活和氢化:由(氯化钴)叔酰胺的快速电活化2被放能释放气体的青睐,得到分离的氯代和Cl -在氯仿中的离子。的B(2,6-F 2 C ^ 6 ħ 3)3 /氯-沮丧路易斯一对可随后裂开ħ 2上的24.3阻挡千卡/摩尔作为限速步骤,导致瞬时化硼酸快速氢化物还原氯代的。建议逐步进行酰胺活化和还原,以实现较温和的反应条件并提高产物收率。
![图像 图像](https://wol-prod-cdn.literatumonline.com/cms/attachment/9cbc6676-c623-482e-aa12-9a97edcb7d3d/ejoc201900827-toc-0001-m.png)