- SINGLE-STEP SYNTHESIS METHOD OF ARYL THIOL AND APPLICATION THEREOF
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The present invention relates to a single-step synthesis method of aryl thiol, and more specifically, to a method of synthesizing aryl thiol in a single-step by making aryl halide react with alkane dithiol in the presence of a transition metal catalyst. According to the present invention, a single-step synthesis method using the transition metal catalyst, the synthesis method which is capable of synthesizing aryl thiol from aryl halide at a high yield, can be provided. Various aryl halides may be applied to the synthesis method. Further, the synthesis method has advantages that an easily usable reagent may be used, operations are simple, and reactions can be performed under mild conditions. In addition, the synthesized aryl thiol may be used in the synthesis of advanced molecules such as diaryl sulfides and benzothiophenes.COPYRIGHT KIPO 2017
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Paragraph 0032; 0033; 0063; 0067; 0068; 0070
(2017/09/02)
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- Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol
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A highly efficient transition metal-catalyzed single-step synthesis of aryl thiols from aryl halides has been developed employing copper(II) catalyst and 1,2-ethanedithiol. The key features are use of readily available reagents, a simple operation, and relatively mild reaction conditions. This new protocol shows a broad substrate scope with excellent functional group compatibility. A variety of aryl thiols are directly prepared from aryl halides in high yields. Furthermore, the aryl thiols are used in situ for the synthesis of more advanced molecules such as diaryl sulfides and benzothiophenes.
- Liu, Yajun,Kim, Jihye,Seo, Heesun,Park, Sunghyouk,Chae, Junghyun
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supporting information
p. 2205 - 2212
(2015/07/27)
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- Modifiable sulfur tethers as directing groups for aromatic C-H acetoxylation reactions
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A designed new class of modifiable sulfur tethers for aromatic C-H bond functionalizations is presented. As a model, the palladium-catalyzed directed acetoxylation reaction was studied. The more challenging sulfoxide tethers were the most effective in this transformation, showing a broad functionality tolerance, high S oxido-redox stability and no catalyst poisoning. Preliminary mechanistic studies indicate that the higher reactivity and selectivity shown by the sulfoxide tethers vs. the corresponding sulfones can be attributed to an extra coordination of the sulfoxide S atom to the catalyst. The utility of the presented methodology to generate structurally interesting aromatic derivatives by a subsequent modification of the S-tether is also exemplified.
- Richter, Heinrich,Beckendorf, Stephan,Mancheno, Olga Garcia
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supporting information; experimental part
p. 295 - 302
(2011/04/16)
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- Aromatic hydroxythiol synthesis using diazonium salts
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A method for the preparation of aromatic hydroxythiols including oxidizing an aromatic aminothiol to form an aminodisulfide compound; forming a bis-diazonium salt of the aminodisulfide compound; and reacting the bis-diazonium salt with water to form an aromatic hydroxyldisulfide compound, which is then reduced to the hydroxythiol. New bis-diazonium aromatic disulfide compounds are also disclosed.
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- Regiocontrolled carbonylsulfanylations at ortho-position of phenols and at α-position of ketones using chlorocarbonylsulfenyl chloride
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Bu3N/AlCl3-promoted [3+2] cyclocondensation between phenols and chlorocarbonylsulfenyl chloride (CCSC; 3) gave 1,3-benzoxathiol-2-ones (2), wherein the acylation of phenols with CCSC (3) and the intramolecular and regioselective ortho-sulfenylation successively proceeded in a one-pot manner. 2-Sulfanylphenols (1) were produced from 2 by mild hydrolysis using NaOH. An analogous Bu3N-promoted [3+2] cyclocondensation between ketones and 3 gave 1,3-oxathioles (7), wherein the α-CH2- position of the ketones was regioselectively sulfenylated.
- Yoshida, Yoshihiro,Ogura, Masahiro,Tanabe, Yoo
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p. 681 - 692
(2007/10/03)
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- HIGH-TEMPERATURE ORGANIC SYNTHESIS. XLI. REACTIONS OF AROMATIC HALOGEN COMPOUNDS WITH HYDROGEN SULFIDE IN THE PRESENCE OF SULFUR
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The reactions of halogenoarenes containing a sufficiently mobile halogen atom with hydrogen sulfide in the presence of elemental sulfur at 90-230 deg C lead to the corresponding sulfides (with yields of up to 87percent).The disulfides, thiols, and arenes are formed at the same time.In the reactions of bromophenols with hydrogen sulfide in the presence of sulfur migration of the halogen atom is observed, and this leads to the formation of isomeric bis(hydroxyphenyl) sulfides and disulfides and 2,4-dibromophenol.It was established that the yield of the reaction products depends on the time, temperature, halogenophenol-sulfur ratio, and delivery rate of hydrogen sulfide.The radical mechanism of the formation of these substances is discussed.
- Papernaya, L. K.,Panova, G. M.,Deryagina, E. N.,Voronkov, M. G.
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p. 1856 - 1862
(2007/10/02)
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- Reductive Cleavage of Ether and Thioether Bonds on 1,3-Benzodioxole and 1,3-Benzoxathiole Derivatives
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The reaction of lithium and sodium diethylamide with 1,3-benzodioxoles and 1,3-benzoxathioles is here reported. 1,3-Benzodioxoles exhibit selective cleavage of the ether bond with formation of alkoxyphenols; 1,3-benzoxathioles when reacting with sodium diethylamide lead to 2-alkoxybenzenethiols while with lithium diethylamide give 2-alkoxybenzenethiols together with 2-(alkylthio)phenols.
- Melis, Stefana,Piras, Pier Paolo,Plumitallo, Antonio,Sotgiu, Francesca
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p. 1413 - 1414
(2007/10/02)
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- Studies on the Synthesis of Heterocyclic Compounds. VIII. Action of Acyl Halides on 2,2-di-n-butyl-1,3,2-benzoxathiastannole, 2-Chloro-1,3,2-benzoxathiaarsole and -stibole
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The cleavage reaction of some 1,3,2-benzoxathiastannole,-arsole and -stibole derivatives with acetyl and benzoyl chloride is described.The reactions were carried out refluxing in benzene or at room temperature.In all cases, the reaction occurs through the initial cleavage of the S-M linkage with formation of the respective o-acylthio derivatives.The structure of the prepared compounds was assigned on the basis of their analytical, physical and spectral data.
- Anchisi, Carlo,Corda, Luciana,Fadda, Anna,Maccioni, Antonio,Podda, Gianni
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p. 649 - 652
(2007/10/02)
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- Preparation of catechol derivatives
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A method of preparing derivatives of aromatic compounds including the catechol function STR1 by replacement of one of the hydroxyls by mercaptan STR2 Cathechol or a multi-ring compound (naphthyl-, anthryl-, phenanthryl-, etc.) containing the catechol function is first reacted with thiophosgene to produce the corresponding dioxole-2-thione STR3 The thione is ammonolyzed to the corresponding hydroxy N,N-disubstituted thionocarbamate STR4 The thionocarbamate is acetylated to STR5 and heated to rearrange the compound to the corresponding thiolcarbamate STR6 Further heating produces the corresponding oxathiol-2-one STR7 which can be hydrolyzed to the corresponding mercaptan STR8
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- Amino substituted arylthio-alkanoic acids having hypolipidemic activity
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This invention relates to novel compounds and compositions of amino substituted arylthio-alkanoic acid, the corresponding pharmaceutically-acceptable salts and the esters thereof. The invention also relates to methods for reducing plasma lipid levels in animals using the compounds of the present invention.
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