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Relevant academic research and scientific papers

Ni nanoparticles on RGO as reusable heterogeneous catalyst: Effect of Ni particle size and intermediate composite structures in C-S cross-coupling reaction

The present work demonstrates the C-S cross-coupling reaction between aryl halides and thiols using nickel nanoparticles (Ni NPs) supported on reduced graphene oxide (Ni/RGO) as a heterogeneous catalyst. It is observed that the uniformly dispersed Ni NPs supported on RGO could exhibit excellent catalytic activity in C-S cross-coupling reactions and the catalytic application is generalized with diverse coupling partners. Although the electron-rich planar RGO surface helps in stabilizing the agglomeration-free Ni NPs, the catalytic process is found to occur involving Ni(II) species and the recovered catalyst containing both Ni(0)/Ni(II) species is equally efficient in recycle runs. A correlation of loading of Ni species, size of NPs and the intermediate Ni-related heterostructures formed during the catalytic process has been established for the first time, and found to be best in the C-S cross-coupling reaction for Ni(0) and Ni(II) NPs of the average sizes 11-12 nm and 4 nm, respectively.

Copper-catalyzed sulfenylation of boronic acids with sulfonyl hydrazides

An unprecedented sulfenylation reaction of carbon-boron bonds has been developed using sulfonyl hydrazides as sulfenyl sources. A range of sulfonyl hydrazides underwent tetrakis(acetonitrile)copper(I) tetrafluoroborate [Cu(CH3CN)4BF4]/2,2′-bipyridine-catalyzed sulfenylation with boronic acids under air to give structurally diverse thioethers in moderate to good yields. Preliminary mechanistic studies show that sulfonyl hydrazides are subjected to decomposition into thiosulfonates and disulfides followed by formation of carbon-sulfur bonds with boronic acids.

Sulfide synthesis through copper-catalyzed C-S bond formation under biomolecule-compatible conditions

We report here an efficient and mild method for constructing C-S bonds. The reactions were carried out with Na2S2O3 as a sulfurating reagent, CuSO4 as a catalyst, and water as solvent without any surfactant. The products were achieved in moderate to excellent yields at room temperature under air. Notably, this reaction is compatible with various biomolecules including amino acids, oligosaccharides, nucleosides, proteins, and cell lysates. This journal is

A well-defined (POCOP)Rh catalyst for the coupling of aryl halides with thiols

This article describes a well-defined pincer-Rh catalyst for C-S cross-coupling reactions. (POCOP)Rh(H)(Cl) serves as an active precatalyst for the coupling of aryl chlorides and bromides with aryl and alkyl thiols under reasonable conditions (3% mol cat., 110 °C, 2-24 h, >90% yield). For select substrates, >90% yields were obtained with catalyst loading as low as 0.1%. Key mechanistic intermediates have been isolated and fully characterized, including (POCOP)Rh(Ph)(SPh) (6a) and (POCOP)Rh(SPh2) (6b). The aryl/bis(phosphinite) (POCOP)Rh system has been shown to favor aryl thiolate reductive elimination at elevated temperatures and in some cases at room temperature, compared with the analogous diarylamido/bis(phosphine) (PNP)Rh pincer system. Concerted reductive elimination has been studied with 6a directly and in the presence of aryl bromide and aryl chloride traps. This investigation demonstrates a clear rate dependence on aryl chloride concentration during catalysis, a dependence that is absent when using aryl bromides. The rate of catalysis is dramatically reduced or brought to zero for ortho-tolyl halides, which can be traced to slower C-S coupling and slower carbon-halogen oxidative addition for ortho-substituted aryls. The influence of the sterics in the thiol component is less straightforward. The S-H oxidative addition product (POCOP)Rh(H)(SPh) (16) has been fully characterized and its reactivity has been examined, resulting in the isolation of the sodium-thiolate adduct (POCOP)Rh(NaSPh) (19). The solid-state structure of 19 shows Na interactions not only with sulfur, but also with a neighboring Rh and the chelating aryl carbon of the pincer framework. The reactivity of 16 and 19 indicates that these potential side products should not hinder catalysis.

A highly efficient Cu-catalyzed S-transfer reaction: From amine to sulfide

A highly efficient Cu-catalyzed dual C-S bonds formation reaction, proceeding in alcohol and water under air, is reported, in which inodorous stable Na2S2O3 is used as a sulfurating reagent. This powerful strategy provides a practical and efficient approach to construct thioethers, using readily available aromatic amines and alkyl halides as starting materials. Sensitive and synthetic useful functional groups could be tolerated. Furthermore, pharmaceuticals, glucose, an amino acid, and a chiral ligand are successfully furnished by this late-stage sulfuration strategy.

Efficient C-S cross-coupling of thiols with aryl iodides catalyzed by Cu(OAc)2·H2O and 2,2′-biimidazole

The classical Ullmann C-S cross coupling reaction of aryl iodides with aromatic/alkyl thiols under catalysis of 15 mol% Cu(OAc)2· H2O and 15 mol% 2,2′-biimidazole works at 80°C in DMSO for 3 h to provide a variety of aryl sulfides in good to excellent yields. The classical Ullmann C-S cross coupling reaction of aryl iodides with aromatic/alkyl thiols under catalysis of 15 mol% Cu(OAc)2· H2O and 15 mol% 2,2′-biimidazole works at 80°C in DMSO for 3 h to provide a variety of aryl sulfides in good to excellent yields. Copyright

Reaction of arylthioniacycloalkane salts with hydrazine

The reaction between arylthioniacycloalkanes (including sulfonium salts with petroleum sulfide moieties) and hydrazine was found to involve the heterocyclic C-S bond cleavage and hydrazine addition to afford ω-hydrazinoalkylsulfides. The stability of ω-hydrazinoalkylsulfides is determined by the nature of substituents on the aromatic ring and by the presence and the position of hydroxy groups, which corresponds with the feasibility of formation of the inner salts betaines. ω-Hydrazinosulfides gradually split out nitrogen and hydrogen; they were stabilized by transformation to the corresponding oxalates. ω-Hydrazinoalkylarylsulfides were also synthesized by reacting ω-chloroalkylarylsulfides with hydrazine. The obtained results may be used for functionalization of petroleum sulfides.

Optically Active Sulfoxides as Ferroelectric Liquid Crystals and Chiral Dopants for Them

Chiral alkylsulfinylbenzenes having an ester functional group at C-4 were prepared and shown for the first time to be ferroelectric liquid crystals and excellent chiral dopants for them.