A Metal-Free Sulfenylation and Bromosulfenylation of Indoles: Controllable Synthesis of 3-Arylthioindoles and 2-Bromo-3-arylthioindoles

被引：133
作者：
Huang, Dayun [1 ]
Chen, Jiuxi [1 ]
Dan, Weixing [1 ]
Ding, Jinchang [1 ,2 ]
Liu, Miaochang [1 ]
Wu, Huayue [1 ]
机构：
[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
[2] Wenzhou Vocat & Tech Coll, Coll Light Ind, Wenzhou 325035, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 11-12期
基金：
中国国家自然科学基金;
关键词：
3-arylthioindoles; 2-bromo-3-arylthioindoles; bromosulfenylation; metal-free conditions; sulfenylation; EFFICIENT SULFENYLATION; CATALYZED SULFENYLATION; QUINONE MONO-O; S-ACETALS; POTENT INHIBITORS; 2ND SULFENYLATION; ARYL SULFONES; 3-SULFENYL; DISULFIDES; 3-SELENYLINDOLES; ARYLTHIOINDOLES;
D O I：
10.1002/adsc.201200227
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient metal-free sulfenylation of indoles with disulfides has been developed, leading to 3-arylthioindoles in moderate to excellent yields. Furthermore, bromosulfenylation of indoles with disulfides has been realized for the first time providing a new family of 2-bromo-3-arylthioindole derivatives in good yield by the one-pot construction of C-S and C-Br bonds. It is noteworthy that the system enables the use of both the RS moieties in RSSR and shows a broad functional group tolerance.
引用
收藏
页码：2123 / 2128
页数：6
相关论文
共 52 条
  • [1] ATKINSON JG, 1988, SYNTHESIS-STUTTGART, P480
  • [2] Nucleophilic reactions in the indole series: displacement of bromine under phase transfer catalysis
    Barraja, Paola
    Diana, Patrizia
    Carbone, Anna
    Cirrincione, Girolamo
    [J]. TETRAHEDRON, 2008, 64 (51) : 11625 - 11631
  • [3] Improved replicon cellular activity of non-nucleoside allosteric inhibitors of HCVNS5B polymerase:: From benzimidazole to indole scaffolds
    Beaulieu, Pierre L.
    Gillard, James
    Bykowski, Darren
    Brochu, Christian
    Dansereau, Nathalie
    Duceppe, Jean-Simon
    Haché, Bruno
    Jakalian, Araz
    Lagacé, Lisette
    LaPlante, Steven
    McKercher, Ginette
    Moreau, Elaine
    Perreault, Stphane
    Stammers, Timothy
    Thauvette, Louise
    Warrington, Jeff
    Kukolj, George
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (19) : 4987 - 4993
  • [4] Bedford, 2011, ANGEW CHEM, V123, P5638
  • [5] Mild C-H Halogenation of Anilides and the Isolation of an Unusual Palladium(I)-Palladium(II) Species
    Bedford, Robin B.
    Haddow, Mairi F.
    Mitchell, Charlotte J.
    Webster, Ruth L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (24) : 5524 - 5527
  • [6] PREPARATION AND DIELS-ALDER REACTIVITY OF SEVERAL NEW CHALCOGEN-HALOGEN SUBSTITUTED BUTADIENES
    BRIDGES, AJ
    FISCHER, JW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (16) : 2954 - 2961
  • [7] A new synthesis of 3-arylthioindoles as selective COX-2 inhibitors using PIFA
    Campbell, JA
    Broka, CA
    Gong, L
    Walker, KAM
    Wang, JH
    [J]. TETRAHEDRON LETTERS, 2004, 45 (21) : 4073 - 4075
  • [8] Synthesis of 3-Sulfenyl- and 3-Selenylindoles by the Pd/Cu-Catalyzed Coupling of N,N-Dialkyl-2-iodoanilines and Terminal Alkynes, Followed by n-Bu4NI-Induced Electrophilic Cyclization
    Chen, Yu
    Cho, Chul-Hee
    Shi, Feng
    Larock, Richard C.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (17) : 6802 - 6811
  • [9] A Novel Synthetic Route to 3-Sulfenyl- and 3-Selenylindoles by n-BU4NI-Induced Electrophilic Cyclization
    Chen, Yu
    Cho, Chul-Hee
    Larock, Richard C.
    [J]. ORGANIC LETTERS, 2009, 11 (01) : 173 - 176
  • [10] Chemistry of the hexahydropyrrolo[2,3-b]indoles:: Configuration, conformation, reactivity, and applications in synthesis
    Crich, David
    Banerjee, Abhisek
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (02) : 151 - 161
123456