Regiospecific Synthesis of 1,2-Disubstituted (Hetero)aryl Fused Imidazoles with Tunable Fluorescent Emission

被引：99
作者：
Zhao, Dongbing
Hu, Junyi
Wu, Ningjie
Huang, Xiaolei
Qin, Xurong
Lan, Jingbo
You, Jingsong [1 ]
机构：
[1] Sichuan Univ, W China Med Sch, Coll Chem, Key Lab Green Chem & Technol,Minist Educ, Chengdu 610064, Peoples R China
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 24期
关键词：
COPPER-CATALYZED SYNTHESIS; LIGHT-EMITTING-DIODES; BENZIMIDAZOLES; DERIVATIVES; AMINATION; DISCOVERY;
D O I：
10.1021/ol202807d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A palladium-catalyzed two or fourfold amination was established that allows regiospecific synthesis of a diversity-oriented library of 1,2-disubstituted (hetero)aryl fused imidazoles, and provides an exceptional tool for the discovery of fluorescent scaffolds with tunable fluorescence emission. These fluorophores have been applied as fluorescent probes for live cell imaging.
引用
收藏
页码：6516 / 6519
页数：4
相关论文
共 35 条
  • [1] BAE JS, 2007, Patent No. 2007011170
  • [2] The high-pressure SNAr reaction of N-p-fluorobenzyl-2-chlorobenzimidazole with amines;: an approach to norastemizole and analogues
    Barrett, IC
    Kerr, MA
    [J]. TETRAHEDRON LETTERS, 1999, 40 (13) : 2439 - 2442
  • [3] Rapid microwave-assisted liquid-phase combinatorial synthesis of 2-(arylamino)benzimidazoles
    Bendale, PM
    Sun, CM
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (04): : 359 - 361
  • [4] Modular fluorescent benzobis(imidazolium) salts: Syntheses, photophysical analyses, and applications
    Boydston, Andrew J.
    Vu, Peter D.
    Dykhno, Olga L.
    Chang, Vicki
    Wyatt, Alvin R., II
    Stockett, Adam S.
    Ritschdbrff, Eric T.
    Shear, Jason B.
    Bielawski, Christopher W.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (10) : 3143 - 3156
  • [5] Phase-tunable fluorophores based upon benzobis(imidazolium) salts
    Boydston, Andrew J.
    Pecinovsky, Cory S.
    Chao, Steven T.
    Bielawski, Christopher W.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (47) : 14550 - +
  • [6] An improved procedure for the synthesis of benzimidazoles, using palladium-catalyzed aryl-amination chemistry
    Brain, CT
    Steer, JT
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) : 6814 - 6816
  • [7] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines
    Brasche, Gordon
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) : 1932 - 1934
  • [8] Combinatorial Discovery of Fluorescent Pharmacophores by Multicomponent Reactions in Droplet Arrays
    Burchak, Olga N.
    Mugherli, Laurent
    Ostuni, Mariano
    Lacapere, Jean Jacques
    Balakirev, Maxim Y.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (26) : 10058 - 10061
  • [9] Developments Towards Regioselective Synthesis of 1,2-Disubstituted Benzimidazoles
    Carvalho, Luisa C. R.
    Fernandes, Eduarda
    Marques, M. Manuel B.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (45) : 12544 - 12555
  • [10] Evolution of red organic light-emitting diodes: Materials and devices
    Chen, CT
    [J]. CHEMISTRY OF MATERIALS, 2004, 16 (23) : 4389 - 4400
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