Amine‐Triggered 6π‐Electrocyclization–Aromatization Cascade of Ynedienamines,Advanced Synthesis & Catalysis

当前位置： X-MOL 学术 › Adv. Synth. Catal. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Amine‐Triggered 6π‐Electrocyclization–Aromatization Cascade of Ynedienamines
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2017-03-20 , DOI: 10.1002/adsc.201601146
Xijian Li _{1,

2} , Huidong Yu ₃ , Yong Huang ₁

Affiliation

An unprecedented 6π‐electrocyclization–aromatization cascade reaction of ynedienamines is described. The electron‐rich ynedienamine is converted by γ‐protonation to an electrophilic allenyl iminium species which is susceptible to amine addition generating a highly electron‐rich triene intermediate. The 6π‐electrocyclization is accelerated by three electron‐donating substituents in a captodative manner. Subsequent redox‐neutral aromatization allows the direct synthesis of 1,3‐diaminobenzenes from readily available ynedienamines.

中文翻译：

胺引发的6π-电环化-芳基化胺级联反应

炔联胺史无前例的6π-电环化-芳构化级联反应被描述。富电子的炔胺通过γ质子化转化为亲电子的烯基亚胺基亚胺，易于加成胺，生成高度电子富集的三烯中间体。三个给电子的取代基以俘获性方式加速了6π电环化。随后的氧化还原中性芳构化可以从容易获得的炔二胺直接合成1,3-二氨基苯。

更新日期：2017-03-20

点击分享查看原文

点击收藏

阅读更多本刊新发论文本刊介绍/投稿指南