Indium-Catalyzed C-S Cross-Coupling of Aryl Halides with Thiols

被引：188
|
作者：
Reddy, V. Prakash [1 ]
Swapna, K. [1 ]
Kumar, A. Vijay [1 ]
Rao, K. Rama [1 ]
机构：
[1] Indian Inst Chem Technol, Div Organ Chem 1, Hyderabad 500007, Andhra Pradesh, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 08期
关键词：
PHOSPHINE OXIDE LIGAND; TRANSITION-METAL; BOND FORMATION; DIARYL SULFIDES; BORONIC ACIDS; IODIDES; THIOETHERS; EFFICIENT; MECHANISM; ARYLATION;
D O I：
10.1021/jo802731j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Indium-catalyzed C-S cross-coupling of aromatic and alkane thiols with aryl halides proceeds smoothly in the presence of In(OTf)(3) (10 mol %), TMEDA (20 mol %), and KOH as a base in DMSO at 135 degrees C. When this protocol was utilized, a variety of thiols could be cross-coupled with aryl halides to afford the corresponding aryl sulfides in good to excellent yields.
引用
收藏
页码：3189 / 3191
页数：3
相关论文
共 50 条
  • [1] A general and inexpensive protocol for the Cu-catalyzed C-S cross-coupling reaction between aryl halides and thiols
    Thomas, Anns Maria
    Asha, Sujatha
    Sindhu, K. S.
    Anilkumar, Gopinathan
    TETRAHEDRON LETTERS, 2015, 56 (47) : 6560 - 6564
  • [2] 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
  • [3] Nano Indium Oxide as a Recyclable Catalyst for C-S Cross-Coupling of Thiols with Aryl Halides under Ligand Free conditions
    Reddy, Vutukuri Prakash
    Kumar, Akkilagunta Vijay
    Swapna, Kokkirala
    Rao, Kakulapati Rama
    ORGANIC LETTERS, 2009, 11 (08) : 1697 - 1700
  • [4] Nickel Phosphite/Phosphine-Catalyzed C-S Cross-Coupling of Aryl Chlorides and Thiols
    Jones, Kieran D.
    Power, Dennis J.
    Bierer, Donald
    Gericke, Kersten M.
    Stewart, Scott G.
    ORGANIC LETTERS, 2018, 20 (01) : 208 - 211
  • [5] Efficient copper-catalyzed C-S cross-coupling of heterocyclic thiols with aryl iodides
    Niu, Liang-Feng
    Cai, Yan
    Liang, Chao
    Hui, Xin-Ping
    Xu, Peng-Fei
    TETRAHEDRON, 2011, 67 (16) : 2878 - 2881
  • [6] Efficient copper(I)-catalyzed C-S cross-coupling of thiols with aryl halides in an aqueous two-phase system
    Zhang, Xin-Yan
    Zhang, Xiao-Yan
    Guo, Sheng-Rong
    JOURNAL OF SULFUR CHEMISTRY, 2011, 32 (01) : 23 - 35
  • [7] Copper-catalyzed cross-coupling reaction of thiols with aryl halides
    Lee, Chin-Fa
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2019, 194 (07) : 678 - 681
  • [8] Silver catalyzed C-C and C-S coupling of aryl halides and thiols with boronic acids
    Das, Rima
    Chakraborty, Debashis
    TETRAHEDRON LETTERS, 2012, 53 (52) : 7023 - 7027
  • [9] Efficient ligand-free nickel-catalyzed C-S cross-coupling of thiols with aryl iodides
    Jammi, Suribabu
    Barua, Priyanka
    Rout, Laxmidhar
    Saha, Prasenjit
    Punnlyamurthy, Tharmalingam
    TETRAHEDRON LETTERS, 2008, 49 (09) : 1484 - 1487
  • [10] C-S cross-coupling of aryl halides with alkyl thiols catalyzed by in-situ generated nickel(II) N-heterocyclic carbene complexes
    Guo, Fang-Jie
    Sun, Jing
    Xu, Zhao-Qing
    Kuhn, Fritz E.
    Zang, Shu-Liang
    Zhou, Ming-Dong
    CATALYSIS COMMUNICATIONS, 2017, 96 : 11 - 14
12345