Ligand-free Cu-catalyzed odorless synthesis of unsymmetrical sulfides through cross-coupling reaction of aryl/benzyl/alkyl halides with an aryl boronic acid/S8 system as a thiolating agent in PEG

被引：37

作者：

Rostami, Abed ^{[1
]}

Rostami, Amin ^{[1
]}

Ghaderi, Arash ^{[2
]}

Zolfigol, Mohammad Ali ^{[3
]}

机构：

[1] Univ Kurdistan, Fac Sci, Dept Chem, Sanandaj 6617715175, Iran

[2] Hormozgan Univ, Coll Sci, Dept Chem, Bandar Abbas 71961, Iran

[3] Bu Ali Sina Univ, Coll Chem, Hamadan 6517838683, Iran

来源：

RSC ADVANCES | 2015年 / 5卷 / 46期

关键词：

ONE-POT SYNTHESIS; BOND FORMATION; COPPER(I) IODIDE; HIGHLY EFFICIENT; S-ARYLATION; NUCLEOPHILIC-SUBSTITUTION; ARYLBORONIC ACIDS; CARBON-DISULFIDE; TANDEM REACTION; O-HALOANILINES;

D O I：

10.1039/c5ra05244k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this article, we have presented a novel, efficient and environmentally benign method for one-pot, one-step and odorless synthesis of a wide range of unsymmetrical sulfides from the reaction of aryl/benzyl/alkyl halides with aryl boronic acids in the presence of S-8, NaOH and a catalytic amount of CuI in PEG200 as green solvent at 40-60 degrees C. The products were obtained in moderate to excellent yields. More importantly, this reaction is applicable for the gram-scale preparation of the desired sulfides.

引用

页码：37060 / 37065

页数：6

共 12 条

[1] Efficient Cu-catalyzed one-pot odorless synthesis of sulfides from triphenyltin chloride, aryl halides and S8 in PEG
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TETRAHEDRON LETTERS, 2016, 57 (02) : 192 - 195
[2] Ligand-Free Copper-Catalyzed Cross-Coupling Reaction of Alkynes with Aryl Iodides and Vinyl Halides
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[3] Palladium catalyzed ligand-free Suzuki cross-coupling reactions of benzylic halides with aryl boronic acids under mild conditions
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TETRAHEDRON LETTERS, 2004, 45 (37) : 6959 - 6962
[4] Pd/C-Catalyzed Ligand-Free Hiyama Cross-Coupling Reaction of Aryl Halides Under Aqueous Conditions
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[5] A general and inexpensive protocol for the Cu-catalyzed C-S cross-coupling reaction between aryl halides and thiols
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TETRAHEDRON LETTERS, 2015, 56 (47) : 6560 - 6564
[6] CuFe2O4 magnetic nanoparticle catalyzed odorless synthesis of sulfides using phenylboronic acid and aryl halides in the presence of S8
Amiri, Kamran
Rostami, Amin
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[7] Copper catalyzed reaction of alcohols, alkyl halides and Na2S2O3: an odorless and ligand-free route to unsymmetrical thioether synthesis
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NEW JOURNAL OF CHEMISTRY, 2022, 46 (33) : 16172 - 16176
[8] Ligand-Free Copper-Catalyzed Synthesis of Asymmetrical Thioethers by Coupling Aryl or Alkyl Halides Using an Acetyl Thiourea Precursor in Wet Polyethylene Glyol (PEG 400)
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PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2015, 190 (04) : 561 - 566
[9] New strategy for the synthesis of N-aryl pyrroles: Cu-catalyzed C-N cross-coupling reaction of trans-4-hydroxy-L-proline with aryl halides
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[10] Synthesis of Cp*CH2PPh2 and its use as a ligand for the nickel-catalyzed cross-coupling reaction of alkyl halides with aryl Grignard reagents
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Oshima, Koichiro
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233

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