NiFe2O4 as a magnetically recoverable nanocatalyst for odourless C-S bond formation via the cleavage of C-O bond in the presence of S8 under mild and green conditions

被引:29
|
作者
Atashkar, Bahareh [1 ]
Rostami, Amin [2 ]
Rostami, Abed [3 ]
Zolfigol, Mohammad Ali [1 ]
机构
[1] Bu Ali Sina Univ, Dept Organ Chem, Fac Chem, Hamadan 6517838683, Iran
[2] Univ Kurdistan, Dept Chem, Fac Sci, Sanandaj 6617715175, Iran
[3] Kurdistan Univ Med Sci, Vice Chancellor Food & Drug, Sanandaj, Iran
基金
美国国家科学基金会;
关键词
C-O bond activation; C-S bond formation; diaryl sulfides; NiFe2O4 magnetic nanoparticles; S-8; CROSS-COUPLING REACTIONS; ONE-POT SYNTHESIS; ARYL ALKYL THIOETHERS; CATALYZED SYNTHESIS; COPPER(I) IODIDE; BORONIC ACIDS; TRIPHENYLTIN CHLORIDE; FERRITE NANOPARTICLES; CARBON-DISULFIDE; EFFICIENT METHOD;
D O I
10.1002/aoc.4691
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
We present green methodologies for one-pot and odourless syntheses of unsymmetric and symmetric diaryl sulfides via CO bond activation using NiFe2O4 magnetic nanoparticles as a reusable heterogeneous nanocatalyst. The synthesis of unsymmetric sulfides is performed using the cross-coupling reaction of phenolic esters such as acetates, triflates and tosylates with arylboronic acid/S-8 or triphenyltin chloride/S-8 as thiolating agents in the presence of base and NiFe2O4 magnetic nanoparticles as a catalyst in poly(ethylene glycol) as solvent at 60-85 degrees C. Also, the synthesis of symmetric diaryl sulfides from phenolic compounds using S-8 as the sulfur source and NiFe2O4 as catalyst in dimethylformamide at 120 degrees C is described. Using these protocols, the syntheses of various unsymmetric and symmetric sulfides become easier than using the available protocols due to the use of a magnetically reusable bimetallic nanocatalyst and avoiding the use of thiols and aryl halides.
引用
收藏
页数:16
相关论文
共 50 条
  • [21] Chemo-and Regioselective 4CR Synthesis of Oxathiaaza[3.3.3] propellanes via Sequential C-S, C-N and C-O Bond Formation in a Single Pot
    Rezvanian, Atieh
    Alizadeh, Abdolali
    Zhu, Long-Guan
    SYNLETT, 2012, (17) : 2526 - 2530
  • [22] CLEAVAGE OF ETHEREAL BOND .7. ACTION OF ALUMINUM AND MAGNESIUM HALIDES ON CONTAINING C-O ETHEREAL AND C-S THIOETHEREAL BONDS COMPOUNDS
    CABIDDU, S
    GELLI, G
    MACCIONI, A
    SECCI, M
    ANNALI DI CHIMICA, 1972, 62 (7-8) : 505 - 512
  • [23] Metal-Free Synthesis of 2-Substituted (N, O, C) Benzothiazoles via an Intramolecular C-S Bond Formation
    Feng, Enguang
    Huang, He
    Zhou, Yu
    Ye, Deju
    Jiang, Hualiang
    Liu, Hong
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (04): : 422 - 429
  • [24] Reactions of TpRu(CO)(NCMe)(Ph) with electron-rich olefins: examples of stoichiometric C-S, C-O and C-H bond cleavage
    Goj, LA
    Lail, M
    Pittard, KA
    Riley, KC
    Gunnoe, TB
    Petersen, JL
    CHEMICAL COMMUNICATIONS, 2006, (09) : 982 - 984
  • [25] Palladium-catalyzed phosphorylation of arylsulfonium salts with P(O)H compounds via C-S bond cleavage
    Liu, Huijin
    Sun, Kai
    Li, Xiaolan
    Zhang, Jie
    Lu, Wei
    Luo, Xuzhong
    Luo, Haiqing
    RSC ADVANCES, 2022, 12 (39) : 25280 - 25283
  • [26] Metal-free C-C, C-O, C-S and C-N bond formation enabled by SBA-15 supported TFMSA
    Yi, Xiangyan
    Feng, Jiajun
    Huang, Fei
    Baell, Jonathan Bayldon
    CHEMICAL COMMUNICATIONS, 2020, 56 (08) : 1243 - 1246
  • [27] A concise synthetic strategy to functionalized chromenones via [5+1] heteroannulation and facile C-N/C-S/C-O bond formation with various nucleophiles
    Savant, Mahesh M.
    Gowda, Neetha S.
    Pansuriya, Akshay M.
    Bhuva, Chirag V.
    Kapuriya, Naval
    Anandalwar, Sridhar M.
    Prasad, Shashidhara J.
    Shah, Anamik
    Naliapara, Yogesh T.
    TETRAHEDRON LETTERS, 2011, 52 (02) : 254 - 257
  • [28] CO2-promoted oxidative cross-coupling reaction for C-S bond formation via masked strategy in an odourless way
    Qiao, Zongjun
    Ge, Nanyang
    Jiang, Xuefeng
    CHEMICAL COMMUNICATIONS, 2015, 51 (51) : 10295 - 10298
  • [29] C–C Bond Cleavage in Oxidation of Aliphatic Hydrocarbons under Mild Conditions in the VV/H2O2/AcOH System
    A. E. Gekhman
    I. P. Stolyarov
    N. V. Ershova
    N. I. Moiseeva
    I. I. Moiseev
    Doklady Chemistry, 2001, 378 : 150 - 153
  • [30] A One-Pot, Transition-Metal-Free Procedure for C-O, C-S, and C-N Bond Formation at the Benzylic Position of Methylarenes
    Shimojo, Hiroyuki
    Moriyama, Katsuhiko
    Togo, Hideo
    SYNTHESIS-STUTTGART, 2015, 47 (09): : 1280 - 1290