Copper-catalyzed chalcogenoamination of 2-alkynylanilines with dichalcogenides for one-step synthesis of 3-sulfenylindoles and 3-selenylindoles

被引：75
|
作者：
Li, Zhen [1 ]
Hong, Longcheng [1 ]
Liu, Ruiting [1 ]
Shen, Jianzhong [1 ]
Zhou, Xigeng [1 ,2 ]
机构：
[1] Fudan Univ, Dept Chem, Shanghai Key Lab Mol Catalysis & Innovat Mat, Shanghai 200433, Peoples R China
[2] State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 12期
基金：
高等学校博士学科点专项科研基金;
关键词：
2-Alkynylaniline; Dichalcogenides; 3-Chalcogenylindole; Copper(I) iodide; FRIEDEL-CRAFTS ALKYLATION; TERMINAL ALKYNES; LEWIS-ACID; SULFENYLATION; DISULFIDES; REACTIVITY; INDOLES; HYDROTHIOLATION; DERIVATIVES; CYCLIZATION;
D O I：
10.1016/j.tetlet.2011.01.052
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The copper-catalyzed chalcogenoamination of 2-alkynylanilines with dichalcogenides has been achieved under mild reaction conditions using the weak base Cs2CO3 in combination with air oxidant, providing a convenient and efficient method for synthesis of 3-sulfenylindoles and 3-selenylindoles, including complex products bearing two attached 3-sulfenylindole rings. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1343 / 1347
页数：5
相关论文
共 50 条
  • [31] A Convenient One-Step Synthesis of Methyl 2-Benzamidomethyl-3-oxobutanoate
    Chao, Mingyong
    Hao, Aiyou
    Wang, Hui
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (03) : 645 - 646
  • [32] One-step aqueous solvothermal synthesis of In2O3 nanocrystals
    Yang, Jun
    Li, Chunxia
    Quan, Zewei
    Kong, Deyan
    Zhang, Xiaoming
    Yang, Piaoping
    Lin, Jun
    CRYSTAL GROWTH & DESIGN, 2008, 8 (02) : 695 - 699
  • [33] SYNTHESIS OF 2,3'-BIINDOLYL FROM INDOLE IN ONE-STEP REACTIONS
    BERGMAN, J
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1973, 10 (01) : 121 - 122
  • [34] ONE-STEP SYNTHESIS OF FUNCTIONALLY SUBSTITUTED DELTA-3-PYRROLIDONES-2
    MOSKALENKO, AS
    PROSYANIK, AV
    KOLTSOV, NY
    NESTEROVA, EY
    NOVOBRANETS, TD
    KOSTYANOVSKII, RG
    BULLETIN OF THE RUSSIAN ACADEMY OF SCIENCES-DIVISION OF CHEMICAL SCIENCE, 1992, 41 (01): : 135 - 135
  • [35] Iridium-Catalyzed Enantioselective and Diastereoselective Allylation of Dioxindoles: A One-Step Synthesis of 3-AllyI-3-hydroxyoxindoles
    He, Rui
    Wu, Shanchao
    Tang, Haoming
    Huo, Xiaohong
    Sun, Zhenliang
    Zhang, Wanbin
    ORGANIC LETTERS, 2018, 20 (19) : 6183 - 6187
  • [36] Copper-catalyzed synthesis of 3-allyl-2-aminoindoles from 3-diazoindolin-2-imines and allyltrimethylsilane
    Lang, Bo
    Zhou, Yuxuan
    Lu, Ping
    Wang, Yanguang
    TETRAHEDRON, 2019, 75 (12) : 1597 - 1604
  • [37] One-step synthesis of symmetrical 3,3′-substituted 2,2′-bipyridine ligands by cobalt(I)-catalyzed [2+2+2] cycloadditions
    Varela, JA
    Castedo, L
    Saá, C
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (46) : 12147 - 12148
  • [38] Selective Synthesis of 2-Indolyl-3-oxoindolines or 2-(2-Aminophenyl)quinolines through Cu(II)- or Bi(III)-Catalyzed Tunable Dimerizations of 2-Alkynylanilines
    Jia, Ruixue
    Li, Bin
    Zhang, Xinying
    Fan, Xuesen
    ORGANIC LETTERS, 2020, 22 (17) : 6810 - 6815
  • [39] Lipase-Catalyzed Regioselective One-Step Synthesis of Penta-O-acetyl-3-hydroxylactal
    Filice, Marco
    Vanna, Renzo
    Terreni, Marco
    Guisan, Jose M.
    Palomo, Jose M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (20) : 3327 - 3329
  • [40] Copper-Catalyzed C(sp2)-C(sp3) Cross-Dehydrogenative Coupling of Quinones with Cyclic Alkanes: One-Step Access to Parvaquone and its Analogs
    Baral, Ek Raj
    Kim, Sung Hong
    Lee, Yong Rok
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (09) : 1134 - 1141
12345