Ligand-controlled palladium catalysis enables switch between mono- and di-arylation of primary aromatic amines with 2-halobenzothiazoles

Herein, a wide range of mono- and di-arylated products were efficiently prepared from C–N coupling of 2-halobenzothiazoles and primary aromatic amines, and representative compounds 3b and 4b were further confirmed by X-ray crystallography. It was noteworthy that the di-arylated products, denoted as...

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Published in:Organic chemistry frontiers an international journal of organic chemistry 2020-08, Vol.7 (15), p.1981-1990
Main Authors: Yan-Qiu, Zhu, Zhang, Rui, Wei, Sang, Hua-Jing, Wang, Wu, Yuan, Bao-Yi, Yu, Jun-Chao, Zhang, Cheng, Hua, Chen, Cheng
Format: Article
Language:English
Subjects:
Amines
Aromatic compounds
Catalysis
Chemical synthesis
Coupling (molecular)
Crystallography
Cytochrome
Cytochrome c
Cytochromes
Diphenyl ether
Ligands
Organic chemistry
Palladium
Pyridines
Reductase
Reductases
X-ray crystallography
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Summary:Herein, a wide range of mono- and di-arylated products were efficiently prepared from C–N coupling of 2-halobenzothiazoles and primary aromatic amines, and representative compounds 3b and 4b were further confirmed by X-ray crystallography. It was noteworthy that the di-arylated products, denoted as di(benzothiazolyl)amines, are new chemical entities which have not yet been reported. Moreover, the ligand-controlled protocol was extended to the synthesis of target molecules bearing a diphenyl ether or diphenyl amine scaffold. To our delight, several compounds exhibited good inhibitory activity against succinate-cytochrome c reductase (SCR), which revealed the practical application of this protocol. Notably, selective mono- and di-arylation could be switched simply by varying the ligand from Xantphos to a pyridine-functionalized N-heterocyclic carbene (NHC) ligand, and further investigations were carried out to elucidate the possible reason for this new finding.
ISSN:2052-4110
2052-4110
DOI:10.1039/d0qo00361a