A general and efficient copper catalyst for the amidation of aryl halides

被引:863
作者
Klapars, A [1 ]
Huang, XH [1 ]
Buchwald, SL [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ja0260465
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An experimentally simple and inexpensive catalyst system was developed for the amidation of aryl halides by using 0.2-10 mol % of Cul, 5-20 mol % of a 1,2-diamine ligand, and K3PO4, K2CO3, or CS2CO3 as base. Catalyst systems based on N,N'-dimethylethylenediamine or trans-N,N'-dimethyl-1,2-cyclohexanediamine were found to be the most active even though several other 1,2-diamine ligands could be used in the easiest cases. Aryl iodides, bromides, and in some cases even aryl chlorides can be efficiently amidated. A variety of functional groups are tolerated in the reaction, including many that are not compatible with Pd-catalyzed amidation or amination methodology.
引用
收藏
页码:7421 / 7428
页数:8
相关论文
共 62 条
  • [21] 2-L
  • [22] Total syntheses of (-)-asperlicin and (-)-asperlicin C
    He, F
    Foxman, BM
    Snider, BB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (25) : 6417 - 6418
  • [23] Hydrogen bonding and structure of 2-hydroxy-N-acylanilines in the solid state and in solution
    Hibbert, F
    Mills, JF
    Nyburg, SC
    Parkins, AW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (03): : 629 - 634
  • [24] SYNTHESIS OF OLIGO(M-ANILINE)
    ITO, A
    SAITO, T
    TANAKA, K
    YAMABE, T
    [J]. TETRAHEDRON LETTERS, 1995, 36 (48) : 8809 - 8812
  • [25] The directed ortho metalation-Ullmann connection. A new Cu(I)-catalyzed variant for the synthesis of substituted diaryl ethers
    Kalinin, AV
    Bower, JF
    Riebel, P
    Snieckus, V
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) : 2986 - 2987
  • [26] STUDIES ON THE SYNTHESES OF HETEROCYCLIC-COMPOUNDS .865. A NOVEL SYNTHESIS OF INDOLE-DERIVATIVES BY INTRAMOLECULAR NUCLEOPHILIC AROMATIC-SUBSTITUTION
    KAMETANI, T
    OHSAWA, T
    IHARA, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (01): : 290 - 294
  • [27] An efficient copper-catalyzed coupling of aryl halides with imidazoles
    Kiyomori, A
    Marcoux, JF
    Buchwald, SL
    [J]. TETRAHEDRON LETTERS, 1999, 40 (14) : 2657 - 2660
  • [28] A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles
    Klapars, A
    Antilla, JC
    Huang, XH
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) : 7727 - 7729
  • [29] Palladium-catalyzed intramolecular C-O bond formation
    Kuwabe, S
    Torraca, KE
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (49) : 12202 - 12206
  • [30] Copper-catalyzed coupling of alkylamines and aryl iodides: An efficient system even in an air atmosphere
    Kwong, FY
    Klapars, A
    Buchwald, SL
    [J]. ORGANIC LETTERS, 2002, 4 (04) : 581 - 584