N-(1-Oxy-2-picolyl)oxalamic acids as a new type of O,O-ligands for the Cu-catalyzed N-arylation of azoles with aryl halides in water or organic solvent

doi:10.1039/c5ob00045a

	N-(1-Oxy-2-picolyl)oxalamic acids as a new type of O,O-ligands for the Cu-catalyzed N-arylation of azoles with aryl halides in water or organic solvent
	Wang, Yongbin 1; Zhang, Yu 3; Yang, Beibei 1; Zhang, Ao2 ; Yao, Qizheng 1
刊名	ORGANIC & BIOMOLECULAR CHEMISTRY
	2015
卷号	13 期号:13 页码:4101-4114
ISSN号	1477-0520
DOI	10.1039/c5ob00045a
文献子类	Article
英文摘要	N-(1-Oxy-pyridin-2-ylmethyl) oxalamic acids (L3-L5) were identified as novel efficient ligands for copper-catalyzed C-N cross-coupling of azoles and aryl halides in water. The N-arylation of imidazoles, indoles and pyrazoles proceeded with moderate to excellent yields and complete selectivity over aromatic amines and phenols. Moreover, L5, which is also efficient in organic solvent with low catalyst loading, can be used to promote the N-arylation reactions with water-sensitive materials. The catalytic mechanism was proposed based on the results of several verification experiments which indicated that the ligands as new-type chelators may coordinate to Cu(I) with two oxygen atoms of N-oxide and amide in the coupling process.
WOS关键词	BOND-FORMING REACTIONS ; NITROGEN-CONTAINING HETEROCYCLES ; COUPLING REACTIONS ; COPPER(I) COMPLEXES ; ARYLBORONIC ACIDS ; HIGHLY EFFICIENT ; ULLMANN REACTION ; MILD CONDITIONS ; IONIC LIQUIDS ; O-ARYLATION
WOS研究方向	Chemistry
语种	英语
出版者	ROYAL SOC CHEMISTRY
WOS记录号	WOS:000351597700030
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/276743]
专题	药物化学研究室
通讯作者	Zhang, Ao
作者单位	1.China Pharmaceut Univ, Sch Pharm, Nanjing 210009, Peoples R China; 2.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 200000, Peoples R China 3.Allist Pharmaceut Inc, Shanghai, Peoples R China;
推荐引用方式 GB/T 7714	Wang, Yongbin,Zhang, Yu,Yang, Beibei,et al. N-(1-Oxy-2-picolyl)oxalamic acids as a new type of O,O-ligands for the Cu-catalyzed N-arylation of azoles with aryl halides in water or organic solvent[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2015,13(13):4101-4114.
APA	Wang, Yongbin,Zhang, Yu,Yang, Beibei,Zhang, Ao,&Yao, Qizheng.(2015).N-(1-Oxy-2-picolyl)oxalamic acids as a new type of O,O-ligands for the Cu-catalyzed N-arylation of azoles with aryl halides in water or organic solvent.ORGANIC & BIOMOLECULAR CHEMISTRY,13(13),4101-4114.
MLA	Wang, Yongbin,et al."N-(1-Oxy-2-picolyl)oxalamic acids as a new type of O,O-ligands for the Cu-catalyzed N-arylation of azoles with aryl halides in water or organic solvent".ORGANIC & BIOMOLECULAR CHEMISTRY 13.13(2015):4101-4114.