胺化
化学
亚胺
组合化学
功能群
选择性
表面改性
苯胺
还原胺化
催化作用
有机化学
聚合物
物理化学
作者
Naveen Yadav,Neha Taneja,Dulal Musib,Chinmoy Kumar Hazra
标识
DOI:10.1002/anie.202301166
摘要
Reversing the conventional site-selectivity of C−H activation provides efficient retrosynthetic disconnections to otherwise unreactive bonds. Described herein is the Brønsted acid-catalyzed reaction that selectively performs meta-amination of anisidines with aliphatic-, heterocyclic- and aromatic amines in a one-pot procedure. In addition to dramatically simplifying the synthesis of meta-substituted anilines, our approach has the advantage of the scalability and remarkable functional group tolerance, including late-stage functionalization of pharmaceutical compounds and natural products. The control experiments and detailed computational analysis provide insight into the reaction mechanism and the origin of meta-selectivity. The protocol extended to the synthesis of challenging tri-aminated arenes and successfully applied for the efficient synthesis of 5-HT6 receptor antagonists, the anti-psychotic drugs viz.. SB-214111, SB-258510, and specifically, anti-schizophrenic drug SB-271046.
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