Synthesis of symmetrical biaryl compounds by homocoupling reaction

被引:51
作者
Vasconcelos, Stanley N. S. [1 ]
Reis, Joel S. [1 ]
de Oliveira, Isadora M. [2 ]
Balfour, Michael N. [1 ]
Stefani, Helio A. [1 ]
机构
[1] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Sao Paulo, SP, Brazil
[2] Univ Sao Paulo, Inst Quim, Sao Paulo, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
CROSS-COUPLING REACTIONS; ARYL GRIGNARD-REAGENTS; PALLADIUM-CATALYZED SYNTHESIS; DIMERIC PYRANONAPHTHOQUINONE CORE; ULTRASOUND-ASSISTED SYNTHESIS; COMPLEX REDUCING AGENTS; ARYLBORONIC ACIDS; C-H; OXIDATIVE DIMERIZATION; ROOM-TEMPERATURE;
D O I
10.1016/j.tet.2019.02.001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Since the development of the Ullmann coupling in the early 20th Century, there has been intense and continuous research on the syntheses of biaryl compounds, which appears as an interesting branch of organic chemistry. A myriad of methodologies for the synthesis of biaryl compounds have been studied and well established, including homocoupling methodologies, which in general are robust as well as consolidated strategies. Biaryl systems are quite relevant building blocks for the synthesis of more complex chemical structures. Besides the diversity of functional groups that can be used to promote a new aryl-aryl bond, there is a wide variety of transition metals that can act as catalyst in these processes. In this review, we summarized numerous methodologies of homocoupling reactions for the synthesis of symmetrical biaryl compounds. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1865 / 1959
页数:95
相关论文
共 231 条
  • [11] THE CHEMISTRY OF ORGANOBISMUTH REAGENTS .13. LIGAND COUPLING INDUCED BY PD(0)
    BARTON, DHR
    OZBALIK, N
    RAMESH, M
    [J]. TETRAHEDRON, 1988, 44 (18) : 5661 - 5668
  • [12] Beller M., 2004, Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals
  • [13] Kumada-Grignard-type biaryl couplings on water
    Bhattacharjya, Anish
    Klumphu, Piyatida
    Lipshutz, Bruce H.
    [J]. NATURE COMMUNICATIONS, 2015, 6
  • [14] Non-peptide angiotensin type 1 receptor antagonists in the treatment of hypertension
    Birkenhäger, WH
    de Leeuw, PW
    [J]. JOURNAL OF HYPERTENSION, 1999, 17 (07) : 873 - 881
  • [15] Bogdanovic B, 2000, ANGEW CHEM INT EDIT, V39, P4610, DOI 10.1002/1521-3773(20001215)39:24<4610::AID-ANIE4610>3.0.CO
  • [16] 2-O
  • [17] THE PREPARATION OF FINELY DIVIDED METAL POWDERS AND TRANSITION-METAL COMPLEXES USING ORGANICALLY SOLVATED MAGNESIUM
    BONNEMANN, H
    BOGDANOVIC, B
    BRINKMANN, R
    SPLIETHOFF, B
    HE, DW
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 451 (1-2) : 23 - 31
  • [18] Cobalt-Catalyzed Oxidative Homocoupling of Arylzinc Species
    Bourne-Branchu, Yann
    Moncomble, Aurelien
    Corpet, Martin
    Danoun, Gregory
    Gosmini, Corinne
    [J]. SYNTHESIS-STUTTGART, 2016, 48 (19): : 3352 - 3356
  • [19] A facile enantioselective synthesis of the dimeric pyranonaphthoquinone core of the cardinalins
    Brimble, Margaret A.
    Gibson, Jennifer S.
    Sejberg, Jimmy J. P.
    Sperry, Jonathan
    [J]. SYNLETT, 2008, (06) : 867 - 870
  • [20] Bringmann G, 2001, PROG CH ORG NAT PROD, V82, P1