Advancing Meta-Selective C–H Amination through Non-Covalent Interactions

Regioselective C–H amination of simple arenes is highly desirable, but accessing meta-sites of ubiquitous arenes has proven challenging due to the lack of both electronic and spatial preference. This study demonstrates the successful use of various privileged nitrogen-containing functionalities foun...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2024-01, Vol.146 (3), p.1735-1741
Main Authors: Lv, Qianqian, Hu, Zongxing, Zhang, Yousong, Zhang, Zhihan, Lei, Honghui
Format: Article
Language:English
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Summary:Regioselective C–H amination of simple arenes is highly desirable, but accessing meta-sites of ubiquitous arenes has proven challenging due to the lack of both electronic and spatial preference. This study demonstrates the successful use of various privileged nitrogen-containing functionalities found in pharmaceutical compounds to direct meta-C–H amination of arenes, overcoming the long-standing requirement for a redundant directing group. The remarkable advancements in functional group accommodation for precise regiochemical control were achieved through the discovery of an unprecedented organo-initiator and the strategic utilization of non-covalent interactions. This protocol has been successfully applied in the concise synthesis and late-stage derivatization of drug molecules, which would have been otherwise challenging to achieve.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.3c09904