Microwave-Assisted Copper-Catalyzed Cross-Coupling Reaction of Thiols with Aryl Iodides in Water

被引:25
|
作者
Chen, Yi-An [1 ]
Badsara, Satpal Singh [1 ]
Tsai, Wan-Ting [1 ]
Lee, Chin-Fa [1 ]
机构
[1] Natl Chung Hsing Univ, Dept Chem, Taichung 402, Taiwan
来源
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 02期
关键词
microwave heating; copper; cross-coupling; thiols; aryl iodides; sulfides; S BOND FORMATION; C-H FUNCTIONALIZATION; LIGAND-FREE; EFFICIENT SYNTHESIS; METAL-FREE; ORGANIC-SYNTHESIS; TE BOND; HALIDES; SULFUR; CONVENIENT;
D O I
10.1055/s-0034-1379206
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Microwave-promoted C-S bond formation from thiols and aryl iodides in the presence of a copper catalyst is reported. A combination of copper(II) oxide and 1,10-phenanthroline catalyzes this reaction. A variety of aryl iodides react smoothly with thiols to provide the corresponding aryl sulfides in good to excellent yields. Notably, the reactions proceed in water with a short reaction time (30 minutes). This system shows broad functional-group tolerance; amino, chloro, bromo, acetyl, and nitro groups are unaffected by the reaction conditions.
引用
收藏
页码:181 / 186
页数:6
相关论文
共 50 条
  • [31] CuO hollow nanosphere-catalyzed cross-coupling of aryl iodides with thiols
    Hyunje Woo
    Balaji Mohan
    Eunjung Heo
    Ji Chan Park
    Hyunjoon Song
    Kang Hyun Park
    [J]. Nanoscale Research Letters, 8
  • [32] Microwave-Assisted, Pd(0)-Catalyzed Cross-Coupling of Diazirines with Aryl Halides
    Zhao, Xia
    Wu, Guojiao
    Yan, Chong
    Lu, Kui
    Li, Hui
    Zhang, Yan
    Wang, Jianbo
    [J]. ORGANIC LETTERS, 2010, 12 (23) : 5580 - 5583
  • [33] Copper-catalyzed coupling of hydroxylamines with aryl iodides
    Jones, Kerri L.
    Porzelle, Achim
    Hall, Adrian
    Woodrow, Michael D.
    Tomkinson, Nicholas C. O.
    [J]. ORGANIC LETTERS, 2008, 10 (05) : 797 - 800
  • [34] Reaction of 1,2-Difunctionalized Ethanes with Aryl Iodides in Copper-catalyzed Cross-Coupling: Application to Synthesis of Phenols
    Kim, Jihye
    Battsengel, Oyunsaikhan
    Liu, Yajun
    Chae, Junghyun
    [J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (12): : 2833 - 2840
  • [35] Microwave-assisted copper catalyzed coupling reaction of aryl halides with terminal alkynes
    Wang, JX
    Liu, ZX
    Hu, YL
    Wei, BG
    Kang, LQ
    [J]. SYNTHETIC COMMUNICATIONS, 2002, 32 (13) : 1937 - 1945
  • [36] Copper-Catalyzed Cross-Coupling of Thiols, Alcohols, and Oxygen for the Synthesis of Esters
    Lim, Seungyeon
    Ji, Miran
    Wang, Xi
    Lee, Chan
    Jang, Hye-Young
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (03) : 591 - 595
  • [37] A New Method for Aromatic Difluoromethylation: Copper-Catalyzed Cross-Coupling and Decarboxylation Sequence from Aryl Iodides
    Fujikawa, Kenichi
    Fujioka, Yasutaka
    Kobayashi, Akira
    Amii, Hideki
    [J]. ORGANIC LETTERS, 2011, 13 (20) : 5560 - 5563
  • [38] Copper-Catalyzed Sulfinyl Cross-Coupling Reaction of Sulfinamides
    Kou, Mengting
    Wei, Ziqiang
    Li, Zhen
    Xu, Bin
    [J]. ORGANIC LETTERS, 2022, 24 (46) : 8514 - 8519
  • [39] Palladium-free copper-catalyzed coupling reaction of aryl iodides and terminal acetylenes in water
    Chen, Gong
    Zhu, Xinhai
    Cai, Jiwen
    Wan, Yiqian
    [J]. SYNTHETIC COMMUNICATIONS, 2007, 37 (7-9) : 1355 - 1361
  • [40] Copper-catalyzed Cross-coupling Reaction between Aryl(trialkyl)silanes and Alkyl Halides
    Komiyama, Takeshi
    Minami, Yasunori
    Hiyama, Tamejiro
    [J]. CHEMISTRY LETTERS, 2018, 47 (08) : 1048 - 1050