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

• Published in: Tetrahedron Vol. 76; no. 8; pp. 130944 - 130950
• Main Authors: Sun, Kai-Xin, Zhou, Jin-Hui, He, Qian-Wei, Shao, Li-Xiong, Lu, Jian-Mei
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 21.02.2020; Elsevier
• Subjects: Amines; Chemistry; Chemistry, Organic; Chemoselective C-N coupling; Dichlorobenzenes; N-heterocyclic carbene-palladium complex; Physical Sciences; Science & Technology; synthetic method; N-heterocyclic carbene-palladium complex; Amines; Chemoselective C-N coupling; synthetic method; Dichlorobenzenes; PRECATALYSTS; C-N; ARYLATION; BUCHWALD-HARTWIG AMINATION; CROSS-COUPLING REACTIONS; ARYL; SUZUKI-MIYAURA REACTIONS; LIGAND; CARBENE COMPLEXES; EFFICIENT
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2020.130944

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.