Direct synthesis of diaryl sulfides by copper-catalyzed coupling of aryl halides with aminothiourea

Wu, Xiang; Hu, Wei

doi:10.1016/j.cclet.2012.01.011

Cited by 22 publications

(4 citation statements)

References 28 publications

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“…They have gained a great deal of attention due to their presence in a number of drugs used for the treatment of Alzheimer's, Parkinson's and inflammatory diseases [1]. In addition, these ligands have been used for the construction of supramolecular architectures that can give rise to mononuclear or binuclear complexes by means of hydrogen bonding and p-p stacking interactions, producing 1D, 2D or 3D network systems [2].…”

Section: Introductionmentioning

confidence: 99%

Versatile coordinating capabilities of thiodibenzoic acid copper complexes bearing N-donor ligands

Moosun

Blair

Coles

et al. 2014

Transition Met Chem

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Cu(II) coordination polymers [Cu(tda)(phen)]-1.5H 2 O (1a), [Cu(tda)(py)] (2a) and [Cu(tda)(bipy)(H 2 O)]-0.5H 2 O (3a) (tda = thiodibenzoic acid, phen = phenanthroline, py = pyridine, bipy = bipyridine) have been synthesized by slow diffusion. Under solvothermal conditions, [Cu(tda)(phen)]2H 2 O (1b), [Cu(tda)(H 2 O)] (2b) and[Cu(tda)(bipy)] (3b) were isolated. The structures of the complexes 1a-3a have been determined by single X-ray diffraction. The experimental X-ray powder diffraction patterns of 1b-3b were compared with the calculated patterns of 1a-3a. The polymers were found to exhibit structural and dimensional diversity due to the effect of the co-ligands. In complexes 1a and 1b, tda is found to coordinate with the metal atom in a monodentate mode, while in 2a and 2b, the carboxylate oxygens are coordinated with the two metal centers in a l-bridged bidentate fashion. The structural analysis of 3a shows that the copper atom is in a square pyramidal environment, whereby the metal atom is coordinated with the carboxylate oxygens of two different tda ligands in a monodentate fashion and two nitrogens of the bipyridine ligand and one coordinated water. The IR spectrum of 3b implies a bidentate mode of coordination.

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Section: Introductionmentioning

confidence: 99%

Versatile coordinating capabilities of thiodibenzoic acid copper complexes bearing N-donor ligands

Moosun

Blair

Coles

et al. 2014

Transition Met Chem

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“…Aminourea is a good surrogate for sulfur upon Cu(OAc) 2 catalysis in DMSO without ligand (Scheme , A) . Using dithiooxamide as a sulfur surrogate in the CuI-catalyzed reaction with PhI required significant optimization since it produced a mixture of diaryl sulfide and diaryl disulfide.…”

Section: Catalytic Cross-coupling Reactions (Z = S Se Te)mentioning

confidence: 99%

Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges

2022

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In the present review, we discuss recent progress in the field of C–Z bond formation reactions (Z = S, Se, Te) catalyzed by transition metals. Two complementary methodologies are consideredcatalytic cross-coupling reactions and catalytic addition reactions. The development of advanced catalytic systems is aimed at improved catalyst efficiency, reduced catalyst loading, better cost efficiency, environmental concerns, and higher selectivity and yields. The important rise of research efforts in sustainability and green chemistry areas is critically assessed. The paramount role of mechanistic studies in the development of a new generation of catalytic systems is addressed, and the key achievements, problems, and challenges are summarized for this field.

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“…Thus, alternative protocols were reported to be used instead of thiols. For instance, S 8 , 12 thiourea, 13,14 dialkyl disulfides, 15 thiocyanates, 16 thioacetamides, 17 amino thiourea, 18 and 1,3-oxathiolanes 19 are some of the odorless alternates to thiols in the C-S cross-coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

Copper chlorophyllin immobilized on ZrO₂ nanoparticle as an effective and green catalyst in the one‐pot thioetherification reaction

Rostamizadeh,

Rahmati

2023

Applied Organom Chemis

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The synthesis of organosulfur compounds gained specific interest in the interference of organic chemistry and chemical biology. Copper chlorophyllin (CC) is a bio‐based copper complex that facilitates the synthesis of organosulfur compounds through the thioetherification reaction. The current paper deals with the immobilization of CC on the ZrO2 nanoparticles (CC@ZrO2) and its application in the one‐pot thioetherification of alkyl and aryl halides using thiourea, an alternative to the bad‐smelling thiols. After the characterization of CC@ZrO2 with different analytical techniques such as FT‐IR, TGA, XPS, N2 adsorption/desorption, XRD, ICP, and FESEM, the catalytic activity of the prepared CC@ZrO2 was evaluated in the synthesis of different types of thioether derivatives. Good to excellent yields, high reusability, and reproducibility made this cost‐effective approach a benchmark in C–S cross‐coupling reactions.

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Direct synthesis of diaryl sulfides by copper-catalyzed coupling of aryl halides with aminothiourea

Cited by 22 publications

References 28 publications

Versatile coordinating capabilities of thiodibenzoic acid copper complexes bearing N-donor ligands

Versatile coordinating capabilities of thiodibenzoic acid copper complexes bearing N-donor ligands

Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges

Copper chlorophyllin immobilized on ZrO₂ nanoparticle as an effective and green catalyst in the one‐pot thioetherification reaction

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Direct synthesis of diaryl sulfides by copper-catalyzed coupling of aryl halides with aminothiourea

Cited by 22 publications

References 28 publications

Versatile coordinating capabilities of thiodibenzoic acid copper complexes bearing N-donor ligands

Versatile coordinating capabilities of thiodibenzoic acid copper complexes bearing N-donor ligands

Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges

Copper chlorophyllin immobilized on ZrO2 nanoparticle as an effective and green catalyst in the one‐pot thioetherification reaction

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Product

Resources

About

Copper chlorophyllin immobilized on ZrO₂ nanoparticle as an effective and green catalyst in the one‐pot thioetherification reaction