Copper-catalyzed amination of aromatic halides with 2-N,N-dimethylaminoethanol as solvent

被引:101
作者
Lu, ZK [1 ]
Twieg, RJ [1 ]
Huang, SPD [1 ]
机构
[1] Kent State Univ, Dept Chem, Kent, OH 44242 USA
关键词
D O I
10.1016/S0040-4039(03)01536-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-catalyzed amination of aromatic halides under mild conditions using N,N-dimethylaminoethanol as solvent is described. We have studied this reaction in some detail varying the copper source. base, water content and other parameters including the scope of useful amine and aromatic halide structures. A variety of 4-halo-N,N-cycloalkylanilines and 2-N,N-cycloalkylaminothiophenes were synthesized for further elaboration into chromophores for optoclectronic applications. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6289 / 6292
页数:4
相关论文
共 36 条
[21]   A general and efficient copper catalyst for the amidation of aryl halides [J].
Klapars, A ;
Huang, XH ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (25) :7421-7428
[22]   Copper-catalyzed coupling of alkylamines and aryl iodides: An efficient system even in an air atmosphere [J].
Kwong, FY ;
Klapars, A ;
Buchwald, SL .
ORGANIC LETTERS, 2002, 4 (04) :581-584
[23]   Copper-promoted C-N bond cross-coupling with phenylstannane [J].
Lam, PYS ;
Vincent, G ;
Bonne, D ;
Clark, CG .
TETRAHEDRON LETTERS, 2002, 43 (16) :3091-3094
[24]   Copper-promoted C-N bond cross-coupling with hypervalent aryl siloxanes and room-temperature N-arylation with aryl iodide [J].
Lam, PYS ;
Deudon, S ;
Averill, KM ;
Li, RH ;
He, MY ;
DeShong, P ;
Clark, CG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (31) :7600-7601
[25]   COPPER ASSISTED NUCLEOPHILIC-SUBSTITUTION OF ARYL HALOGEN [J].
LINDLEY, J .
TETRAHEDRON, 1984, 40 (09) :1433-1456
[26]   NEW SYNTHETIC APPLICATIONS OF ARYLLEAD TRIACETATES - N-ARYLATION OF AZOLES [J].
LOPEZALVARADO, P ;
AVENDANO, C ;
MENENDEZ, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) :5678-5682
[27]   Accelerating effect induced by the structure of α-amino acid in the copper-catalyzed coupling reaction of aryl halides with α-amino acids.: Synthesis of benzolactam-V8 [J].
Ma, DW ;
Zhang, YD ;
Yao, JC ;
Wu, SH ;
Tao, FG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (48) :12459-12467
[28]   A general copper-catalyzed synthesis of diaryl ethers [J].
Marcoux, JF ;
Doye, S ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (43) :10539-10540
[29]   FUNCTIONALIZED AZO DYES BY DIRECT ULLMANN COUPLING [J].
MILLER, RD ;
LEE, VY ;
TWIEG, RJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (02) :245-246
[30]   Practical palladium catalysts for C-N and C-O bond formation [J].
Muci, AR ;
Buchwald, SL .
CROSS-COUPLING REACTIONS: A PRACTICAL GUIDE, 2002, 219 :131-209