Selective direct C–H polyfluoroarylation of electron-deficient N-heterocyclic compounds

The first C2-selective direct C–H polyfluoroarylation of electron-deficient N-heterocycles with polyfluorobenzoic acid via the decarboxylative arylation process was achieved by using CuBr2 as the mediator in the green solvent diglyme. The key to success is using the N-methylation activation strategy...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2020-12, Vol.7 (23), p.3887-3895
Main Authors: Li, Shun, Wen-Jing, Li, Yang, Xiao, Sun, Rui, Tang, Juan, Xue-Li, Zheng, Mao-Ling, Yuan, Rui-Xiang, Li, Chen, Hua, Hai-Yan, Fu
Format: Article
Language:English
Subjects:
Copper bromide
Crystallography
Functional groups
Heterocyclic compounds
Methylation
Organic chemistry
Substrates
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Summary:The first C2-selective direct C–H polyfluoroarylation of electron-deficient N-heterocycles with polyfluorobenzoic acid via the decarboxylative arylation process was achieved by using CuBr2 as the mediator in the green solvent diglyme. The key to success is using the N-methylation activation strategy and TBAB as an important additive. The protocol features broad substrate scope, ligand- and base-free conditions, and good functional group compatibility, and offers a powerful synthetic tool for assembling various polyfluoroarylated N-heterocycles.
ISSN:2052-4110
2052-4110
DOI:10.1039/d0qo00923g