Copper/N, N, N′, N′-Tetramethylethylenediamine-Catalyzed Synthesis of N-Substituted Benzoheterocycles via C-S Cross-Coupling at Ambient Temperature in Water

被引:30
|
作者
Zhao, Na [1 ]
Liu, Liang [1 ]
Wang, Fei [1 ]
Li, Jia [1 ]
Zhang, Wu [1 ]
机构
[1] Anhui Normal Univ, Key Lab Funct Mol Solids, Anhui Lab Mol Based Mat, Coll Chem & Mat Sci,Minist Educ, Wuhu 241000, Peoples R China
基金
中国国家自然科学基金;
关键词
ambient temperature reaction; copper/N; N; '-tetramethylethylenediamine; (Cu/TMEDA); C-S cross-coupling; N-substituted benzoheterocycles; water; RETINOIC ACID METABOLISM; ONE-POT SYNTHESIS; BOND FORMATION; ROOM-TEMPERATURE; TERMINAL ALKYNES; 3-COMPONENT SYNTHESIS; TANDEM REACTION; 2-AMINOBENZOTHIAZOLES; EFFICIENT; ISOTHIOCYANATES;
D O I
10.1002/adsc.201400043
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Copper/N, N, N', N'-tetramethylethylenediamine (Cu/TMEDA)-catalyzed ambient temperature tandem reactions of isothiocyanates with 2-iodophenols or 2-iodoanilines in water without the protection of an inert atmosphere are described, which provide a simple, rapid, environmental method for the synthesis of a variety of 2-iminobenzo-1, 3-oxathioles and 2-aminobenzothiazoles in good yields. More important, the present reaction process needs only low amounts of copper catalyst (< 1 mol%) and can yield the products on a gram scale.
引用
收藏
页码:2575 / 2579
页数:5
相关论文
共 50 条
  • [21] Synthesis of Benzimidazoles via Domino Intra and Intermolecular C-N Cross-Coupling Reaction
    Kondraganti, Lakshmi
    Manabolu, Surendra Babu
    Dittakavi, Ramachandran
    CHEMISTRYSELECT, 2018, 3 (42): : 11744 - 11748
  • [22] Framework-Copper-Catalyzed C-N Cross-Coupling of Arylboronic Acids with Imidazole: Convenient and Ligand-Free Synthesis of N-Arylimidazoles
    Devarajan, Nainamalai
    Suresh, Palaniswamy
    CHEMCATCHEM, 2016, 8 (18) : 2953 - 2960
  • [23] Iron-catalyzed aerobic oxidative cross-coupling amidation of N,N-dimethylanilines
    Wusiman, Abudureheman
    Hudabaierdi, Ruzeahong
    TETRAHEDRON LETTERS, 2019, 60 (09) : 681 - 683
  • [24] Synthesis of N-substituted Acridinediones and Polyhydroquinoline Derivatives in Refluxing Water
    Xia, Jing-Jing
    Zhang, Ke-Hua
    MOLECULES, 2012, 17 (05): : 5339 - 5345
  • [25] Copper-Catalyzed Carbonylative Cross-Coupling of Arylboronic Acids with N-Chloroamines for the Synthesis of Aryl Amides
    Yin, Zhiping
    Wang, Zechao
    Li, Wanfang
    Wu, Xiao-Feng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (13) : 1769 - 1772
  • [26] C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated nickel(II) N-heterocyclic carbene complexes
    Guo, Fang-Jie
    Sun, Jing
    Xu, Zhao-Qing
    Kuhn, Fritz E.
    Zang, Shu-Liang
    Zhou, Ming-Dong
    CATALYSIS COMMUNICATIONS, 2017, 96 : 11 - 14
  • [27] Copper-catalyzed N-arylation of bis(indolyl)methanes: the first approach for the synthesis of unsymmetrical N-aryl bis(indolyl)methanes by C-N cross-coupling reaction
    Bagheri, Fatemeh Hassani
    Khabazzadeh, Hojatollah
    Fayazi, Maryam
    COMPTES RENDUS CHIMIE, 2021, 24 (02) : 305 - 317
  • [28] Synthesis of Vinyl Sulfides by Copper-Catalyzed Decarboxylative C-S Cross-Coupling
    Ranjit, Sadananda
    Duan, Zhongyu
    Zhang, Pengfei
    Liu, Xiaogang
    ORGANIC LETTERS, 2010, 12 (18) : 4134 - 4136
  • [29] The synthesis of aryl cyanamides through C-N cross-coupling
    Kondraganti, Lakshmi
    Manabolu, Surendra Babu
    Dittakavi, Rama Chandran
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2018, 95 (06) : 629 - 634
  • [30] Iron-Catalyzed Inexpensive and Practical Synthesis of N-Substituted Pyrroles in Water
    Azizi, Najmedin
    Khajeh-Amiri, Alireza
    Ghafuri, Hossein
    Bolourtchian, Mohammad
    Saidi, Mohammad Reza
    SYNLETT, 2009, (14) : 2245 - 2248