Copper-Catalyzed Electrophilic Amination of Arylboronic Acids with Anthranils: An Access to N‑Aryl-2-aminophenones

An efficient copper-catalyzed electrophilic amination strategy has been established for the rapid synthesis of N-aryl-2-aminophenones from readily available arylboronic acids/esters and anthranils. This protocol features good functional group tolerance, broad substrate scope, and operational simplic...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-08, Vol.85 (15), p.10222-10231
Main Authors: Gao, Yang, Yang, Simin, Li, Yibiao, Huo, Yanping, Huang, Zongyi, Chen, Zumin, Hu, Xiao-Qiang
Format: Article
Language:English
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Summary:An efficient copper-catalyzed electrophilic amination strategy has been established for the rapid synthesis of N-aryl-2-aminophenones from readily available arylboronic acids/esters and anthranils. This protocol features good functional group tolerance, broad substrate scope, and operational simplicity. Moreover, a tandem C–H borylation and C–N coupling protocol has also been developed to transform simple arenes to the valuable N-aryl-2-aminophenones in one pot. Additionally, the synthetic potential of this methodology is further demonstrated by the synthesis of various useful N-heterocycles and derivatives.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01109