Glyoxal bis(phenylhydrazone) as promoter for CuI-catalyzed O-arylation of phenols with bromoarenes

被引:32
作者
Liu, Yu-Hua [1 ,2 ]
Li, Gang [1 ,2 ]
Yang, Lian-Ming [1 ]
机构
[1] Chinese Acad Sci, New Mat Lab, Inst Chem, BNLMS, Beijing 100190, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
DIARYL ETHER SYNTHESIS; COUPLING REACTION; ARYL HALIDES; COPPER; LIGAND; NITROGEN; BONDS;
D O I
10.1016/j.tetlet.2008.11.005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A very simple bishydrazone-type ligand, glyoxal bis(phenylhydrazone) (L1), was found to effectively promote the CuI-catalyzed O-arylation of phenols with aryl bromides. This cross-coupling reaction proceeded in acetonitrile at 60-80 degrees C in the presence of K3PO4 as base. A diverse array of phenols and bromoarenes was employed as Substrates to afford diaryl ethers in good to excellent yields, and some base-sensitive groups, such as ester, aldehyde, and ketone groups, can survive under the mild reaction conditions. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:343 / 346
页数:4
相关论文
共 16 条
  • [1] Copper in cross-coupling reactions - The post-Ullmann chemistry
    Beletskaya, IP
    Cheprakov, AV
    [J]. COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) : 2337 - 2364
  • [2] Ullmann diaryl ether synthesis: Rate acceleration by 2,2,6,6-tetramethylheptane-3,5-dione
    Buck, E
    Song, ZJ
    Tschaen, D
    Dormer, PG
    Volante, RP
    Reider, PJ
    [J]. ORGANIC LETTERS, 2002, 4 (09) : 1623 - 1626
  • [3] Mild Ullmann-type biaryl ether formation reaction by combination of ortho-substituent and ligand effects
    Cai, Q
    Zou, BL
    Ma, DW
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (08) : 1276 - 1279
  • [4] Selected patented cross-coupling reaction technologies
    Corbet, Jean-Pierre
    Mignani, Gerard
    [J]. CHEMICAL REVIEWS, 2006, 106 (07) : 2651 - 2710
  • [5] A general and mild Ullmann-type synthesis of diaryl ethers
    Cristau, HJ
    Cellier, PP
    Hamada, S
    Spindler, JF
    Taillefer, M
    [J]. ORGANIC LETTERS, 2004, 6 (06) : 913 - 916
  • [6] Synthesis of diaryl ethers using an easy-to-prepare, air-stable, soluble copper(I) catalyst
    Gujadhur, R
    Venkataraman, D
    [J]. SYNTHETIC COMMUNICATIONS, 2001, 31 (18) : 2865 - 2879
  • [7] Formation of aryl-nitrogen, aryl-oxygen, and aryl-carbon bonds using well-defined copper(I)-based catalysts
    Gujadhur, RK
    Bates, CG
    Venkataraman, D
    [J]. ORGANIC LETTERS, 2001, 3 (26) : 4315 - 4317
  • [8] COPPER ASSISTED NUCLEOPHILIC-SUBSTITUTION OF ARYL HALOGEN
    LINDLEY, J
    [J]. TETRAHEDRON, 1984, 40 (09) : 1433 - 1456
  • [9] N,N-Dimethyl glycine-promoted Ullmann coupling reaction of phenols and aryl halides
    Ma, DW
    Cai, Q
    [J]. ORGANIC LETTERS, 2003, 5 (21) : 3799 - 3802
  • [10] Phosphine-free hydrazone-Pd complex as the catalyst precursor for a Suzuki-Miyaura reaction under mild aerobic conditions
    Mino, T
    Shirae, Y
    Sakamoto, M
    Fujita, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) : 2191 - 2194