Direct amination of anilines utilizing dearomatized phenolate species

Authors: 
Shaofeng Wu*, Haitao Li, Shicheng Dong, Xiaoyu Pan, Haochen Liu, Ziren Chen, Fei Xue, Bin Wang, Yu Xia, Lei Zhou, Yonghong Zhang, Jun Zhu*, and Chenjiang Liu*
Journal: 
Org. Lett.
Year: 
2025
Volume: 
27
FirstPage-LastPage: 
ASAP
TOC: 
Abstract: 

Activation of the aryl C–N bond underpins critical challenges in modern organic synthesis. Herein, the direct amination of anilines is presented via hypervalent iodine-mediated transient dearomatized phenolate intermediates, enabling selective C(aryl)–NH2 bond cleavage under mild conditions. A library of bioactive p-alkylaminophenols is synthesized in up to 85% yields within 3 h. Being used in late-stage drug diversification and mechanistic studies, this protocol offers a modular platform for complex amine construction.

https://doi.org/10.1021/acs.orglett.5c01314

Doi: 
10.1021/acs.orglett.5c01314