Metal-free, iodine-catalyzed regioselective sulfenylation of indoles with thiols

被引：77
|
作者：
Yi, Shanli [1 ]
Li, Meichao [1 ]
Mo, Weimin [1 ]
Hu, Xinquan [1 ]
Hu, Baoxiang [1 ]
Sun, Nan [1 ]
Jin, Liqun [1 ]
Shen, Zhenlu [1 ]
机构：
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 17期
基金：
中国国家自然科学基金;
关键词：
Indoles; Thiols; Sulfenylation; Iodine; DMSO; INTRAMOLECULAR CYCLIZATION; EFFICIENT SULFENYLATION; CONTROLLABLE SYNTHESIS; 2ND SULFENYLATION; ARYL SULFONES; DISULFIDES; THIOLATION; SYSTEM; 3-SULFENYLATION; THIOPHENOLS;
D O I：
10.1016/j.tetlet.2016.03.073
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An iodine-catalyzed regioselective sulfenylation of indoles in the presence of DMSO has been presented. Various indoles can react with aryl thiols or alkyl thiols to afford their corresponding 3-sulfenylindoles in good to excellent yields. The notable features of this protocol include easy operation, metal-free reaction conditions, and excellent functional group tolerance. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1912 / 1916
页数：5
相关论文
共 50 条
  • [41] Metal free sulfenylation and bis-sulfenylation of indoles: persulfate mediated synthesis
    Prasad, Ch. Durga
    Kumar, Shailesh
    Satter, Moh.
    Adhikary, Amit
    Kumar, Sangit
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (46) : 8036 - 8040
  • [42] One-pot iodine-catalyzed regioselective cycloalkenylation on arylamines
    Massawe, Nancy
    Taylor, Mikaela
    Fotie, Jean
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [43] Iodine-Catalyzed Methylthiolative Annulation of 2-Alkynyl Biaryls with DMSO: A Metal-Free Approach to 9-Sulfenylphenanthrenes
    Mukherjee, Nilanjana
    Chatterjee, Tanmay
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (11): : 7881 - 7890
  • [44] Metal-free molecular iodine-catalyzed direct sulfonylation of pyrazolones with sodium sulfinates leading to sulfonated pyrazoles at room temperature
    Wei, Wei
    Cui, Huanhuan
    Yang, Daoshan
    Liu, Xiaoxia
    He, Chenglong
    Dai, Shicui
    Wang, Hua
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (01): : 26 - 30
  • [45] Iodine-catalyzed oxidative system for 3-sulfenylation of indoles with disulfides using DMSO as oxidant under ambient conditions in dimethyl carbonate
    Ge, Wenlei
    Wei, Yunyang
    [J]. GREEN CHEMISTRY, 2012, 14 (07) : 2066 - 2070
  • [46] Metal-free regioselective construction of indolin-3-ones via hypervalent iodine oxidation of N-substituted indoles
    Jiang, Chao
    Jiang, Chao
    Cheng, Guanyun
    Huang, Baofu
    Xue, Fengtian
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [47] Metal-free regioselective construction of indolin-3-ones via hypervalent iodine oxidation of N-substituted indoles
    Yang, Chao
    Cheng, Guanyun
    Huang, Baofu
    Xue, Fengtian
    Jiang, Chao
    [J]. RSC ADVANCES, 2016, 6 (90): : 87134 - 87141
  • [48] A HIGHLY EFFICIENT, IODINE-CATALYZED GLYCOSYLATION REACTION OF ALCOHOLS, PHENOLS, AND THIOLS
    HOUSTON, TA
    KLEMKE, E
    KOREEDA, M
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 533 - ORGN
  • [49] Iodine-Catalyzed Regioselective Sulfenylation of 4H-Pyrido-[1,2-a]pyrimidin-4-ones with Sulfonyl Hydrazides
    Liu, Wenjie
    Wang, Shaohua
    Cai, Zhihao
    Li, Ziying
    Liu, Jianwen
    Wang, Anda
    [J]. SYNLETT, 2018, 29 (01) : 116 - 120
  • [50] Iron-Catalyzed Sulfenylation of Indoles with Disulfides Promoted by a Catalytic Amount of Iodine
    Fang, Xiao-Li
    Tang, Ri-Yuan
    Zhong, Ping
    Li, Jin-Heng
    [J]. SYNTHESIS-STUTTGART, 2009, (24): : 4183 - 4189
12345