Biaryl Construction via Ni-Catalyzed C-O Activation of Phenolic Carboxylates

被引:337
作者
Guan, Bing-Tao [1 ,2 ]
Wang, Yang [1 ,2 ]
Li, Bi-Jie [1 ,2 ]
Yu, Da-Gang [1 ,2 ]
Shi, Zhang-Jie [1 ,2 ,3 ]
机构
[1] Peking Univ, BNLMS, Beijing 100871, Peoples R China
[2] Peking Univ, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
[3] Chinese Acad Sci, State Key Lab Oganomet Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/ja8056503
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Biaryl scaffolds were constructed via Ni-catalyzed aryl C-O activation by avoiding cleavage of the more reactive acyl C-O bond aryl carboxylates. Now aryl esters, in general, can be successfully employed in cross-coupling reactions for the first time. The substrate scope and synthetic utility of the chemistry were demonstrated by the syntheses of more than 40 biaryls and by constructing complex organic molecules. Water was observed to play an important role in facilitating this transformation.
引用
收藏
页码:14468 / +
页数:4
相关论文
共 35 条
  • [1] ALEXANDER Z, 2003, ANGEW CHEM INT EDIT, V42, P5394
  • [2] Nonpeptidic ligands for peptide-activated g protein-coupled receptors
    Blakeney, Jade S.
    Reid, Robert C.
    Le, Giang T.
    Fairlie, David P.
    [J]. CHEMICAL REVIEWS, 2007, 107 (07) : 2960 - 3041
  • [3] Böhm VPW, 2000, ANGEW CHEM INT EDIT, V39, P1602, DOI 10.1002/(SICI)1521-3773(20000502)39:9<1602::AID-ANIE1602>3.0.CO
  • [4] 2-N
  • [5] Iron-catalyzed reactions in organic synthesis
    Bolm, C
    Legros, J
    Le Paih, J
    Zani, L
    [J]. CHEMICAL REVIEWS, 2004, 104 (12) : 6217 - 6254
  • [6] ANTI-HIV MICHELLAMINES FROM ANCISTROCLADUS-KORUPENSIS
    BOYD, MR
    HALLOCK, YF
    MANFREDI, KP
    BLUNT, JW
    MCMAHON, JB
    BUCKHEIT, RW
    BRINGMANN, G
    SCHAFFER, M
    CRAGG, GM
    THOMAS, DW
    JATO, JG
    CARDELLINA, JH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) : 1740 - 1745
  • [7] Nickel-catalyzed cross-coupling of aryl Grignard reagents with aromatic alkyl ethers: An efficient synthesis of unsymmetrical biaryls
    Dankwardt, JW
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (18) : 2428 - 2432
  • [8] Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222
  • [9] Sustainable metal catalysis with iron: From rust to a rising star?
    Enthaler, Stephan
    Junge, Kathrin
    Beller, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (18) : 3317 - 3321
  • [10] Advances in iron catalyzed cross coupling reactions
    Fürstner, A
    Martin, R
    [J]. CHEMISTRY LETTERS, 2005, 34 (05) : 624 - 629