Efficient ligand-free copper-catalyzed C-S cross-coupling of thiols with aryl iodides using KF/Al2O3 as base

被引:57
|
作者
Feng, Yi-Si [1 ,2 ]
Li, Yuan-Yuan [1 ]
Tang, Lin [1 ]
Wu, Wei [1 ]
Xu, Hua-Jian [1 ,2 ]
机构
[1] Hefei Univ Technol, Sch Chem Engn, Hefei 230009, Peoples R China
[2] Anhui Key Lab Controllable Chem React & Mat Chem, Hefei 230009, Peoples R China
基金
中国国家自然科学基金;
关键词
SULFUR BOND FORMATION; PHOSPHINE OXIDE LIGAND; IMPROVED PROTOCOL; HIGHLY EFFICIENT; RECENT PROGRESS; BORONIC ACIDS; SOLUBLE BASE; HALIDES; CARBON; THIOETHERS;
D O I
10.1016/j.tetlet.2010.02.155
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report a mild, convenient, environmentally friendly, and ligand-free synthetic protocol for the cross-coupling reaction of aryl iodides and thiols using 10 mol % CuI with KF/Al2O3 as the base, in DMF at 110 degrees C. Using this protocol, we have shown that a variety of aryl sulfides can be synthesized in excellent yields from readily available iodides and Olio's. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2489 / 2492
页数:4
相关论文
共 50 条
  • [21] Copper-catalyzed cross-coupling of aryl iodides and aryl acetylenes using microwave heating
    He, H
    Wu, YJ
    TETRAHEDRON LETTERS, 2004, 45 (16) : 3237 - 3239
  • [22] A mild and efficient copper-catalyzed coupling of aryl iodides and thiols using an oxime-phosphine oxide ligand
    Zhu, Di
    Xu, Lei
    Wu, Fan
    Wan, Boshun
    TETRAHEDRON LETTERS, 2006, 47 (32) : 5781 - 5784
  • [23] Synthesis of diaryl ethers through the copper-catalyzed arylation of phenols with aryl iodides using KF/Al2O3
    Hosseinzadeh, Rahman
    Tajbakhsh, Mahmood
    Mohadjerani, Maryam
    Rezaei, Parizad
    Alikarami, Mohammad
    SYNTHETIC COMMUNICATIONS, 2008, 38 (17) : 3023 - 3031
  • [24] Copper-Catalyzed Coupling of Aryl Halides with Terminal Alkynes in the Presence of KF/Al2O3
    Hosseinzadeh, Rahman
    Mohadjerani, Maryam
    Tavakoli, Rahmatollah
    Alikarami, Mohammad
    SYNTHETIC COMMUNICATIONS, 2010, 40 (02) : 282 - 288
  • [25] Efficient copper(I)-catalyzed C-S cross coupling of thiols with aryl halides in water
    Rout, Laxmidhar
    Saha, Prasenjit
    Jammi, Suribabu
    Punniyamurthy, Tharmalingam
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (04) : 640 - 643
  • [26] Indium-Catalyzed C-S Cross-Coupling of Aryl Halides with Thiols
    Reddy, V. Prakash
    Swapna, K.
    Kumar, A. Vijay
    Rao, K. Rama
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (08): : 3189 - 3191
  • [27] Copper-catalyzed cross-coupling of aryl halides and thiols using microwave heating
    Wu, YJ
    He, H
    SYNLETT, 2003, (12) : 1789 - 1790
  • [28] Copper(I) selenophene-2-carboxylate (CuSC) promoted C-S cross-coupling reaction of thiols with aryl iodides
    do Rego Barros, Olga Soares
    Silva, Francielle Rodrigues
    Nunes, Vanessa Loren
    JOURNAL OF SULFUR CHEMISTRY, 2019, 40 (01) : 9 - 17
  • [29] Highly efficient copper-catalyzed formation of N-aryl diazoles using KF/Al2O3
    Hosseinzadeh, Rahman
    Tajbakhsh, Mahmood
    Alikarami, Mohammad
    SYNLETT, 2006, (13) : 2124 - 2126
  • [30] TBAB-promoted ligand-free copper-catalyzed cross-coupling reactions of aryl halides with arylboronic acids
    Li, Jin-Heng
    Li, Ji-Lan
    Xie, Ye-Xiang
    SYNTHESIS-STUTTGART, 2007, (07): : 984 - 988