3169-85-5

Upstream product

• 137-07-5 2-amino-benzenethiol 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 1765-93-1 4-fluoroboronic acid 
• 1141-88-4 2-Aminophenyl disulfide 
• 88-73-3 2-Chloronitrobenzene 
• 95-16-9 1,3-Benzothiazole 
• 352-34-1 4-fluoro-1-iodobenzene 
• 371-42-6 4-Fluorothiophenol 
• 3169-84-4 1-[(4-fluorophenyl)thio]-2-nitrobenzene 

Downstream Products

• 868161-02-8 1-{2-[(4-fluorophenyl)sulfanyl]phenyl}hydrazine hydrochloride 
• 1629-26-1 2-(4-fluorophenyl)-benzothiazole 

Relevant academic research and scientific papers

Di- tert-butyl Peroxide-Mediated Radical C(sp2/sp3)-S Bond Cleavage and Group-Transfer Cyclization

A novel strategy of cascade radical C(sp2/sp3)-S bond cleavage and group-transfer cyclization is disclosed. Triggered by alkyl radicals, varieties of 2-isocyanoaryl thioethers containing aliphatic, aryl, and heteroaromatic groups can be cleaved and precisely reinstalled to give benzothiazole derivatives. Mechanistic studies reveal that the cascade reaction undertakes an intermolecular pathway, and the inner radical sources (R radicals) exhibit high priority over those of methyl radical origin from di-tert-butyl peroxide.

NOVEL TRIAZINE COMPOUND, AND ORGANIC ELECTRONIC ELEMENT AND PLANT-GROWING LIGHTING THAT USE THE SAME

PROBLEM TO BE SOLVED: To provide a triazine compound which has a high triplet energy level and excellent heat resistance, and can be used as an organic electronic element material realizing an element with high efficiency, low voltage and a long life. SOLUTION: In the triazine compound, as represented by the general formula [1] in the figure, a triazine backbone moiety is linked to a dibenzofuran or dibenzothiophene backbone moiety via a biphenyl backbone moiety, where X is an oxygen atom or sulfur atom. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT

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

A convenient and efficient copper-catalyzed synthesis of unsymmetrical and symmetrical diaryl chalcogenides from arylboronic acids in ethanol at room temperature

A simple and convenient approach for the synthesis of unsymmetrical diaryl chalcogenides (Te, Se, and S) has been developed by copper-catalyzed cross-coupling reaction of organoboronic acid with diaryl dichalcogenide in ethanol using NaBH4 in air or oxygen. The present methodology is highly practical for the synthesis of unsymmetrical diaryl tellurides with various functionalities such as -NO2, -F, -Br, and -COOH that have been obtained in good to excellent yields. Methodology is also effective for the synthesis of unsymmetrical diaryl selenides and sulfides. Moreover, symmetrical diaryl selenides have also been obtained from arylboronic acids using elemental selenium powder under optimized reaction conditions. The use of NaBH 4 is the key for the development of milder reaction conditions, which enable the construction of unsymmetrical diaryl chalcogenides from boronic acid substrates in ethanol at room temperature.

Unexpectedly ligand-free copper-catalyzed C-S cross-coupling of benzothiazole with aryl iodides in aqueous solution

A novel synthetic protocol for 2-aminophenyl sulfide derivatives via the reactions of benzothiazole with aryl iodides was reported for the first time. The reactions were catalyzed by CuCl with tetrabutylammonium hydroxide as the base and water as the solvent without ligand at 50°C or room temperature. A variety of aryl iodides underwent the C-S cross-coupling reaction with benzothiazole to afford smoothly the corresponding products in excellent yield.

Copper powder catalyzed direct ring-opening arylation of benzazoles with aryl iodides in polyethylene glycol

The expedient and efficient copper powder catalyzed direct ring-opening arylation of benzazoles with aryl iodides in polyethylene glycol that proceeds in the absence of an added ligand has been developed. The protocol provides facile access to 2-(arylthio)anilines and 2-phenoxyanilines in high yields with a wide tolerance of functional groups. Transmission electron microscopy confirmed that the active catalyst results from the in situ generation of copper nanoparticles under standard reaction conditions, which is an alternative avenue to develop a highly effective metallic copper catalyst. Moreover, the catalytic system can be recycled up to six times. Copyright

Recyclable heterogeneous supported copper-catalyzed coupling of thiols with aryl halides: base-controlled differential arylthiolation of bromoiodobenzenes

Alumina-supported copper sulfate efficiently catalyzes the 5-arylation of aromatic, heteroaromatic and aliphatic thiols with aryl as well as heteroaryl halides under aerobic, ligand-free conditions. This protocol provides an easy access to a variety of thioethers as well as unsymmetrical bis-thioethers by base-controlled differential coupling of thiols with iodo- and bromo-substituents in an aromatic halide. The catalyst is inexpensive, non-air sensitive, environmentally friendly and recyclable.