- Exploration of the mechanism and scope of the CuI/DABCO catalysed C–S coupling reaction
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A cost effective and easily available CuI/DABCO catalytic system has been developed for the C–S cross-coupling reaction. This method is extremely useful for the thioetherification of aryl and heteroaryl halides, providing excellent yields and good chemoselectivity. We have also explored the mechanism of the reaction using DFT studies.
- Thomas, Anns Maria,Sherin,Asha, Sujatha,Manojkumar,Anilkumar, Gopinathan
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Read Online
- Synthesis of 4-amino-4′-nitrodiphenyl sulfide
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The possibility of preparing 4-amino-4′-nitrodiphenyl sulfide by reaction of chlorobenzene with sodium sulfide in a two-phase system composed of water and organic solvent in the presence of a phase-transfer catalyst under continuous hydroacoustic treatment was examined.
- Pilyugin
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Read Online
- Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: Synthesis of diarylsulfides
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A NiCl2/2,2′-bipyridine-catalyzed cross-coupling of thiophenols with arylboronic acids has been developed for the synthesis of symmetric and unsymmetric diarylsulfides at room temperature and in air. This methodology is reliable and offers a mild and easy to operate process for the synthesis of arylthioethers, which are essential compounds with applications in the pharmaceutical and agricultural industries. This method avoids the use of expensive transition metals, such as Pd, Ir or Rh, sophisticated ligands and elevated temperatures. It also has a wide substrate scope (55 examples) and provides products in good to excellent yields (72-93%).
- Bhowmik, Amit,Fernandes, Rodney A.,Yadav, Mahesh
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p. 2447 - 2458
(2020/04/15)
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- C-S coupling with nitro group as leaving group via simple inorganic salt catalysis
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An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition-elimination mechanism.
- Xuan, Maojie,Lu, Chunlei,Lin, Bo-Lin
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supporting information
(2019/08/26)
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- Cerium catalyst promoted C-S cross-coupling: Synthesis of thioethers, dapsone and RN-18 precursors
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In this work, we present a novel, efficient and green methodology for the synthesis of thioethers by the C-S cross-coupling reaction with the assistance of [Ce(l-Pro)2]2Ox as a heterogeneous catalyst in good to excellent yields. A scale-up of the protocol was explored using an unpublished methodology for the synthesis of a dapsone-precursor, which proved to be very effective over a short time. The catalyst [Ce(l-Pro)2]2Ox was recovered and it was shown to be effective for five more reaction cycles.
- Tavares Junior, José M. Da C.,Da Silva, Caren D. G.,Dos Santos, Beatriz F.,Souza, Nicole S.,De Oliveira, Aline R.,Kupfer, Vicente L.,Rinaldi, Andrelson W.,Domingues, Nelson L. C.
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supporting information
p. 10103 - 10108
(2019/12/23)
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- Regioselective thiolation of electron rich arenes and heterocycles in recyclable catalytic media
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A convenient and novel approach has been developed for the synthesis of unsymmetrical diaryl sulfides by the reaction of sulfonyl hydrazides with phenols using a [Bmim][Br] ionic liquid through the formation of C-S bonds. The reaction has further been extended to indole, β-naphthol and aromatic amine moieties. This protocol offers a new, versatile and greener approach for thiolation of natural phenols (monoterpenes)/aromatic phenols/β-naphthols/aromatic amines and indoles without using any catalyst. A broad range of functional groups were well tolerated in this reaction system.
- Raghuvanshi, Dushyant Singh,Verma, Narsingh
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p. 22860 - 22868
(2017/07/10)
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- A general and inexpensive protocol for the Cu-catalyzed C-S cross-coupling reaction between aryl halides and thiols
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A cost effective and easily available CuI/DABCO catalytic system has been developed for C-S cross-coupling reaction. This method is extremely useful for the thioetherification of aryl and heteroaryl halides providing excellent yields and good chemoselectivity.
- Thomas, Anns Maria,Asha, Sujatha,Sindhu,Anilkumar, Gopinathan
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supporting information
p. 6560 - 6564
(2015/11/09)
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- Arylthiolation of arylamine derivatives with (arylthio)-pyrrolidine-2,5-diones
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A simple and efficient method for arylthiolation of arylamines has been developed. The protocol uses (arylthio)pyrrolidine-2,5-diones as the arylthiolating reagents, acetonitrile as the solvent, and no catalyst and additive are required, which avoids contamination from the transition metal catalysts in the target products. Therefore, the present method should provide a convenient, efficient and practical strategy for the synthesis of other aryl sulfides.
- Tian, Hua,Yang, Haijun,Zhu, Changjin,Fu, Hua
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supporting information
p. 481 - 488
(2015/03/05)
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- FeF3/i2-catalyzed synthesis of 4-chalcogen- substituted arylamines by direct thiolation of an arene C-H bond
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An efficient regioselective synthesis of 4-chalcogen-substituted-arylamines by FeF3-catalyzed sulfenylation and selenation of arylamines has been developed. In the presence of FeF3and I2, a variety of arylamines underwent the reaction with disulfides or diselenides to afford the corresponding 4-sulfenyl-or 4-selenenyl-arylamines in moderate to good yields. Georg Thieme Verlag Stuttgart.
- Fang, Xiao-Li,Tang, Ri-Yuan,Zhang, Xing-Guo,Li, Jin-Heng
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experimental part
p. 1099 - 1105
(2011/05/14)
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- One-pot synthesis of amine-substituted aryl sulfides and benzo[ b ]thiophene derivatives
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A series of amine-substituted aryl sulfides have been synthesized from nitroaryl halides via a simple one-pot procedure involving metal-free C-S cross-coupling and in situ nitro group reduction. Various nitroaryl halides were reacted with thiols in recyclable poly(ethylene glycol) to afford the amine-substituted aryl sulfides in high yield. Additionally, the cross-coupling reactions of nitro- and aldehyde-substituted aryl halides with benzyl thiols under the same reaction conditions were demonstrated to afford benzothiazole and phenylbenzo[b]thiophene derivatives.
- Duan, Zhongyu,Ranjit, Sadananda,Liu, Xiaogang
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supporting information; experimental part
p. 2430 - 2433
(2010/07/10)
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- PROCESS FOR SYNTHESIS OF 4-4'-DIAMINO-DIPHENYL-SULFONE
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A new process for the preparation and purification of 4-4'-diamino-diphenyl-sulfone (dapsone) is described. The process described is a three step process comprising a condensation reaction with the synthesis of a thioeter intermediate and then steps of oxidation and reduction in suitable conditions in order to obtain a product with good yield and purity.
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Page/Page column 7
(2008/06/13)
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- Synthesis of 2-amino-5(6)-(4-aminophenyl)benzimidazole derivatives: II. Reaction of 2-nitro-4-thiocyanatoaniline with 4-nitrochlorobenzene
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The reaction of 2-nitro-4-thiocyanatoaniline with 4-nitrochlorobenzene in aqueous alkaline medium in the presence of phase-transfer catalyst at 95-100°C was studied with a view to obtain 4-amino-3,4′- dinitrodiphenyl sulfide. Optimal conditions for the synthesis and isolation of the product were found.
- Pilyugin,Sapozhnikov,Shitov
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p. 979 - 984
(2007/10/03)
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- Process for the partial reduction of polynitrated diaryl compounds
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Polynitrated diaryl compounds of the formula given in the description are reduced with 1-2 mols of sulphides, or compounds which donate sulphide ions, per mol of nitro group in the presence of 0.5-10 mols of ammonia per mol of starting compound at 30°-110° C. to give nitroamino-diaryl compounds, for example 4,4'-dinitro-dibenzyl-2,2'-disulphonic acid is reduced to 4-nitro-4'-amino-stilbene-2,2'-disulphonic acid.
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- Synthesis of a series of new N1-[4-(4-nitrophenylthio)phenyl]-N3-(H/alkyl/acyl/aryl) thioureas and their antifungal, insecticidal and larvicidal activities
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A series of new mono and disubstituted thioureas, derived from 4-(4-nitrophenylthio) aniline, have been prepared and screened for antifungal activity against Alternaria alternata and Curvularia lunata. Their insecticidal and larvicidal activities have also been evaluated against adult male and female cockroaches (Periplanata americana) and mosquito larvae (Culex pipiens fatigans Wied) of IIIrd and early IVth instar stage, respectively. The tabulated results reveal that most of the thiourea derivatives, in general, possess marked antifungal, insecticidal and larvicidal properties, but the chlorosubstituted derivatives, in particular, are the most active compounds in the entire series. Compound 20, n1-[4-(4-nitrophenylthio)phenyl]-N3-(4-chlorophenyl) thiourea, was the most active antifungal compound, whereas, compound 12, N1[4-(4-nitrophenylthio)phenyl]-N3-(4-chlorobenzoyl) thiourea, was the most potent insecticidal and larvicidal compound.
- Shankar,Pandeya
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p. 753 - 756
(2007/10/02)
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