Mild and Efficient Cobalt-Catalyzed Cross-Coupling of Aliphatic Amides and Aryl Iodides in Water

被引：10
|
作者：
Tan, Bryan Yong-Hao [1 ]
Teo, Yong-Chua [1 ]
机构：
[1] Nanyang Technol Univ, Nat Sci & Sci Educ, Natl Inst Educ, Singapore 637616, Singapore
来源：
SYNLETT | 2015年 / 26卷 / 12期
关键词：
cobalt; N-arylation; cross-coupling; aliphatic amide; water; C-N; PROSTATE-CANCER; BOND FORMATION; FLUTAMIDE; COPPER; HALIDES; AMIDATION; CHEMISTRY; LIGANDS; COMPLEXES;
D O I：
10.1055/s-0034-1380724
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient protocol for the C-N cross-coupling of aliphatic amides and iodobenzene is demonstrated using a simple and inexpensive Co(C2O4)2H(2)O/N,N-dimethylethylenediamine (DMEDA) catalytic system in water. Good yields of N-arylated products were isolated (up to 85%) and the protocol has been successfully applied to the synthesis of the anticancer drug, flutamide.
引用
收藏
页码：1697 / 1701
页数：5
相关论文
共 50 条
  • [1] Cobalt-Catalyzed Cross-Coupling Reactions Aryl Halides
    Gosmini, Corinne
    Moncomble, Aurelien
    ISRAEL JOURNAL OF CHEMISTRY, 2010, 50 (5-6) : 568 - 576
  • [2] Cobalt-Catalyzed Cross-Coupling of α-Bromo Amides with Grignard Reagents
    Barde, E.
    Guerinot, A.
    Cossy, J.
    ORGANIC LETTERS, 2017, 19 (22) : 6068 - 6071
  • [3] Cobalt-catalyzed cross-coupling reactions
    Gosmini, Corinne
    Begouin, Jeanne-Marie
    Moncomble, Aurelien
    CHEMICAL COMMUNICATIONS, 2008, (28) : 3221 - 3233
  • [4] Cobalt-Catalyzed Cross-Coupling Reactions
    Cahiez, Gerard
    Moyeux, Alban
    CHEMICAL REVIEWS, 2010, 110 (03) : 1435 - 1462
  • [5] Efficient cobalt-catalyzed C-N cross-coupling reaction between benzamide and aryl iodide in water
    Tan, Bryan Yong-Hao
    Teo, Yong-Chua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (38) : 7478 - 7481
  • [6] Cobalt-Catalyzed Cross-Coupling Reactions of Arylboronic Esters and Aryl Halides
    Duong, Hung A.
    Wu, Wenqin
    Teo, Yu-Yuan
    ORGANOMETALLICS, 2017, 36 (22) : 4363 - 4366
  • [7] Direct Cobalt-Catalyzed Cross-Coupling Between Aryl and Alkyl Halides
    Czaplik, Waldemar Maximilian
    Mayer, Matthias
    Jacobi von Wangelin, Axel
    SYNLETT, 2009, (18) : 2931 - 2934
  • [8] Cobalt-Catalyzed Cross-Coupling Reactions of Aryl Triflates and Lithium Arylborates
    Duong, Hung A.
    Yeow, Zong-Han
    Tiong, Yong-Lun
    Kamal, Nur Haidah Binte Mohamad
    Wu, Wenqin
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (19): : 12686 - 12691
  • [9] Introduction of Cyclopropyl and Cyclobutyl Ring on Alkyl Iodides through Cobalt-Catalyzed Cross-Coupling
    Andersen, Claire
    Ferey, Vincent
    Daumas, Marc
    Bernardelli, Patrick
    Guerinot, Amandine
    Cossy, Janine
    ORGANIC LETTERS, 2019, 21 (07) : 2285 - 2289
  • [10] Cobalt-Catalyzed Cross-Coupling of Functionalized Alkylzinc Reagents with (Hetero)Aryl Halides
    Lutter, Ferdinand H.
    Grokenberger, Lucie
    Spiess, Philipp
    Hammann, Jeffrey M.
    Karaghiosoff, Konstantin
    Knochel, Paul
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (14) : 5546 - 5550
12345