N-heterocyclic carbene-Pd(II)-2-methyl-4,5-dihydrooxazole complex-catalyzed highly chemoselective mono-amination of dichlorobenzenes

The palladium-catalyzed chemoselective mono-amination of dichlorobenzenes was reported in this paper. Under the suitable conditions, all reactions involving the three isomers of dichlorobenzenes with various secondary and primary amines in the presence of a well-defined N-heterocyclic carbene-pallad...

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Bibliographic Details
Published in:Tetrahedron 2020-02, Vol.76 (8), p.130944, Article 130944
Main Authors: Sun, Kai-Xin, Zhou, Jin-Hui, He, Qian-Wei, Shao, Li-Xiong, Lu, Jian-Mei
Format: Article
Language:English
Subjects:
Amines
Chemoselective C-N coupling
Dichlorobenzenes
N-heterocyclic carbene-palladium complex
synthetic method
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Summary:The palladium-catalyzed chemoselective mono-amination of dichlorobenzenes was reported in this paper. Under the suitable conditions, all reactions involving the three isomers of dichlorobenzenes with various secondary and primary amines in the presence of a well-defined N-heterocyclic carbene-palladium(II)-2-methyl-4,5-dihydrooxazole complex, gave the desired mono-aminated products in moderate to high yields as the major or sole one. [Display omitted] •The palladium-catalyzed chemoselective amination of dichlorobenzenes was achieved in this paper..•All reactions took place well to give the desired highly chemoselective mono-aminated products as the major or sole one.•This is the first example of phosphine free, easily available NHC-Pd(II) complex catalyzed chemoselective C-N coupling of dichlorobenzenes.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.130944