Synthesis of Aryl Hydrazines via CuI/BMPO Catalyzed Cross-Coupling of Aryl Halides with Hydrazine Hydrate in Water

被引:22
作者
Kumar, Siripuram Vijay [1 ]
Ma, Dawei [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Ctr Excellence Mol Synth,Univ Chinese Acad Sci, 345 Lingling Lu, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
hydrazine hydrate; cross-coupling; aryl halides; ligand effects; copper; synthetic methods; (HETERO)ARYL CHLORIDES; EFFICIENT SYNTHESIS; AMINATION; CHEMISTRY; AMINES; SCOPE;
D O I
10.1002/cjoc.201800326
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The N,N'-bis(2,6-dimethylphenyl)oxalamide was discovered as a powerful ligand for Cu-catalyzed cross-coupling of aryl halides with hydrazine hydrate, leading to the formation of a variety of aryl hydrazines at 80 C-o in water under the assistance of K3PO4 and 4 mol% cetyltrimethylammonium bromide from aryl bromides and aryl iodides. Good to excellent yields were observed in most cases.
引用
收藏
页码:1003 / 1006
页数:4
相关论文
共 39 条
[31]   Recent advances in the chemistry of indazoles [J].
Schmidt, Andreas ;
Beutler, Ariane ;
Snovvdovych, Bohdan .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (24) :4073-4095
[32]  
Shaughnessy K.H., 2014, Organic Reactions, V85, P1
[33]  
Strohriegl P, 2002, ADV MATER, V14, P1439, DOI 10.1002/1521-4095(20021016)14:20<1439::AID-ADMA1439>3.0.CO
[34]  
2-H
[35]  
Sundberg R. J., 1999, INDOLES
[36]   Dialkylbiaryl phosphines in Pd-catalyzed amination: a user's guide [J].
Surry, David S. ;
Buchwald, Stephen L. .
CHEMICAL SCIENCE, 2011, 2 (01) :27-50
[37]   Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions [J].
Xia, Shanghua ;
Gan, Lu ;
Wang, Kaihang ;
Li, Zheng ;
Ma, Dawei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (41) :13493-13496
[38]  
Zerga A., 2005, CURR MED CHEM, V12, P589
[39]   CuI/Oxalic Diamide Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amines [J].
Zhou, Wei ;
Fan, Mengang ;
Yin, Junli ;
Jiang, Yongwen ;
Ma, Dawei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (37) :11942-11945