C-S Coupling Reaction of Heteroaromatic Compounds via Copper Catalyst

被引:5
|
作者
Zhang, Bianxiang [1 ]
Chen, Kai [1 ]
Yang, Lihua [1 ]
Zhang, Ruijie [1 ]
Zhang, Lina [1 ]
Shi, Ruixue [1 ]
机构
[1] Shanxi Univ, Sch Chem & Chem Engn, Taiyuan 030006, Peoples R China
关键词
aryl thioether; benzo heterocyclic compounds; diphenyl disulfide; HPLC; ADHESION MOLECULE-1 INTERACTION; P-ARYLTHIO CINNAMIDES; RECENT PROGRESS; BOND FORMATION; DISULFIDES; HALIDES; ANTAGONISTS; 3-SULFENYL; OXIDATION; EFFICIENT;
D O I
10.6023/cjoc201410009
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this study, the direct copper-catalyzed C-S coupling reaction of heterocyclic compounds with diphenyl disulfide, without the existence of ligands and alkalis, has been developed. It showed that the yield of target product was 89.9% when the reaction was carried out at 110 degrees C, the reaction time was 12 h, dimethylsulfoxide (DMSO) was used as solvents, and the molar ratio of heterocyclic compound to biphenyl disulfide was 2 : 1. The structures of the target products were confirmed with H-1 NMR and C-13 NMR. The effects of various conditions on the reaction were investigated by high performance liquid chromatography (HPLC) analysis and its reaction mechanism was discussed.
引用
收藏
页码:905 / 909
页数:5
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共 34 条
  • [1] Rhodium-catalyzed reductive coupling of disulfides and diselenides with alkyl halides, using hydrogen as a reducing agent
    Ajiki, K
    Hirano, M
    Tanaka, K
    [J]. ORGANIC LETTERS, 2005, 7 (19) : 4193 - 4195
  • [2] Aromatic homolytic substitution using solid phase synthesis
    Allin, SM
    Bowman, WR
    Karim, R
    Rahman, SS
    [J]. TETRAHEDRON, 2006, 62 (18) : 4306 - 4316
  • [3] A Solvent- and Metal-Free Synthesis of 3-Chacogenyl-indoles Employing DMSO/I2 as an Eco-friendly Catalytic Oxidation System
    Azeredo, Juliano B.
    Godoi, Marcelo
    Martins, Guilherme M.
    Silveira, Claudio C.
    Braga, Antonio L.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09) : 4125 - 4130
  • [4] Synthesis and structure-activity relationships of retinoid X receptor selective diaryl sulfide analogs of retinoic acid
    Beard, RL
    Colon, DF
    Song, TK
    Davies, PJA
    Kochhar, DM
    Chandraratna, RAS
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (18) : 3556 - 3563
  • [5] Use of Base Control To Provide High Selectivity between Diaryl Thioether and Diaryl Disulfide for C-S Coupling Reactions of Aryl Halides and Sulfur and a Mechanistic Study
    Chen, Hsing-Ying
    Peng, Wei-Te
    Lee, Ying-Hsien
    Chang, Yu-Lun
    Chen, Yen-Jen
    Lai, Yi-Chun
    Jheng, Nai-Yuan
    Chen, Hsuan-Ying
    [J]. ORGANOMETALLICS, 2013, 32 (19) : 5514 - 5522
  • [6] 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
  • [7] New arylthioindoles: Potent inhibitors of tubulin polymerization. 2. Structure-activity relationships and molecular modeling studies
    De Martino, G
    Edler, MC
    La Regina, G
    Coluccia, A
    Barbera, MC
    Barrow, D
    Nicholson, RI
    Chiosis, G
    Brancale, A
    Hamel, E
    Artico, M
    Silvestri, R
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (03) : 947 - 954
  • [8] Experimental and Theoretical Investigations of Consequence of Ionic Liquid Anion on Copper(I) Catalyzed Reaction of Aryl Iodide and Thiols
    Deshmukh, Krishna M.
    Madyal, Rupa S.
    Qureshi, Ziyauddin S.
    Gaikar, Vilas G.
    Bhanage, Bhalchandra M.
    [J]. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2013, 52 (13) : 4747 - 4757
  • [9] 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
  • [10] Copper-catalyzed direct thiolation of benzoxazole with diaryl disulfides and aryl thiols
    Fukuzawa, Shin-ichi
    Shimizu, Eiji
    Atsuumi, Yuka
    Haga, Masatake
    Ogata, Kenichi
    [J]. TETRAHEDRON LETTERS, 2009, 50 (20) : 2374 - 2376