Palladium-Catalyzed Direct Arylation of Free NH2-Substituted Thiophene Derivatives

被引:67
|
作者
Derridj, Fazia
Roger, Julien [1 ]
Djebbar, Safia
Doucet, Henri [1 ]
机构
[1] Univ Rennes Catalyse & Organometall, Inst Sci Chim Rennes, CNRS UMR 6226, F-35042 Rennes, France
关键词
C-H ARYLATION; COUPLING REACTIONS; ARYL HALIDES; FUNCTIONALIZATION; HETEROAROMATICS; CYCLIZATION; CLEAVAGE;
D O I
10.1021/ol101758w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalyzed direct 2- or 5-arylation of some free NH2-substituted thiophene derivatives was found to proceed in high yields using a variety of aryl bromides. In the course of these reactions, no coupling of the aryl bromide with the thiophene NH2 substituent was detected. The presence of an ester substituent on C2 of thiophene was found to be useful to block this highly reactive carbon.
引用
收藏
页码:4320 / 4323
页数:4
相关论文
共 50 条
  • [1] Palladium-catalyzed direct arylation using free NH2 substituted thiophene derivatives with inhibition of amination type reaction
    Derridj, Fazia
    Larbi, Karima Si
    Roger, Julien
    Djebbar, Safia
    Doucet, Henri
    TETRAHEDRON, 2012, 68 (36) : 7463 - 7471
  • [2] Ladderization of polystyrene derivatives by palladium-catalyzed polymer direct arylation
    Takagi, Koji
    Tanaka, Hidetoshi
    Mikami, Koichiro
    POLYMER CHEMISTRY, 2019, 10 (21) : 2647 - 2652
  • [3] Palladium-catalyzed direct 5-arylation of formyl- or acetyl-halothiophene derivatives
    Beydoun, Kassem
    Doucet, Henri
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (09) : 1749 - 1759
  • [4] Palladium-Catalyzed Direct C7-Arylation of Substituted Indazoles
    Naas, Mohammed
    El Kazzouli, Said
    Essassi, El Mokhtar
    Bousmina, Mosto
    Guillaumet, Gerald
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16) : 7286 - 7293
  • [5] Palladium-Catalyzed Direct Arylation of Selenophene
    Rampon, Daniel S.
    Wessjohann, Ludger A.
    Schneider, Paulo H.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (13) : 5987 - 5992
  • [6] Direct Palladium-Catalyzed β-Arylation of Lactams
    Chen, Ming
    Liu, Feipeng
    Dong, Guangbin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (14) : 3815 - 3819
  • [7] Cyclopentyl Methyl Ether: An Alternative Solvent for Palladium-Catalyzed Direct Arylation of Heteroaromatics
    Beydoun, Kassem
    Doucet, Henri
    CHEMSUSCHEM, 2011, 4 (04) : 526 - 534
  • [8] Palladium-Catalysed Direct 5-Arylation of Furfurylamine or 2-(Aminoalkyl)thiophene Derivatives
    Roger, Julien
    Doucet, Henri
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (23) : 4412 - 4425
  • [9] Palladium-Catalyzed Direct Arylation of Thiophenes Bearing SO2R Substituents
    Bheeter, Charles Beromeo
    Bera, Jitendra K.
    Doucet, Henri
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (15) : 6407 - 6413
  • [10] Palladium-Catalyzed Direct Ortho C-H Arylation of 2-Arylpyridine Derivatives with Aryltrimethoxysilane
    Li, Wu
    Yin, Zhangwei
    Jiang, Xiaoqing
    Sun, Peipei
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (20) : 8543 - 8548