83859-33-0

Upstream product

• 4028-63-1 iodomesitylene 
• 645-96-5 Benzeneselenol 
• 5707-04-0 Phenylselenyl chloride 
• 108-67-8 1,3,5-trimethyl-benzene 
• 1666-13-3 diphenyl diselenide 
• 2179-79-5 phenyl selenocyanate 
• 5980-97-2 mesitylboronic acid 
• 25862-09-3 phenylmethyl selenoxide 
• 4346-64-9 selenoanisole 
• 71518-92-8 dimesityl diselenide 
• 603-33-8 triphenylbismuthane 
• 59344-64-8 tris(2,4,6-trimethylphenyl)bismuth 

Relevant academic research and scientific papers

Copper-Silver Dual Catalyzed Decyanative C–Se Cross-Coupling

Traditionally, a metal-catalyzed cross-coupling reaction is governed by displacement of leaving groups such as halogens, tosylates, etc. by different nucleophiles leading to the formation of carbon-carbon and carbon-heteroatom bonds. Besides displacement of traditional leaving groups in coupling reactions decyanative cross-coupling has also received current attention. The objective of this work is to develop a decyanative cross-coupling through metal-assisted nucleophilic displacement, which is less explored so far. Thus, a decyanative cross-coupling of aryl selenocyanate with aryl-/alkylacetylenes, boronic acids and silanes has been accomplished by a copper-assisted nucleophilic displacement reaction for an easy access to a series of diaryl, aryl alkyl, aryl vinyl and aryl alkynyl selenides. The best yield of product was obtained using 5 mol% of Cu(OAc)2, Ag2CO3(20 mol%) and Cs2CO3(1 equiv.) at 100 °C for 8 h in N-methylpyrrolidinone (NMP). The advantages of simple operation, high yields and general applicability make this procedure more attractive. A mechanistic pathway has been proposed. Silver plays a key role in the decyanation process. A plausible mechanistic pathway of this decyanative carbon-selenium cross-coupling has been proposed based on UV, EPR, HR-MS and IR analytical data along with results obtained from control experiments. (Figure presented.).

Synthesis of Unsymmetrical Diaryl Selenides: Copper-Catalyzed Se-Arylation of Diaryl Diselenides with Triarylbismuthanes

Copper-catalyzed C(aryl)-Se bond formation by the reaction of diaryl diselenides with triarylbismuthanes in the presence of copper(I) acetate (10 mol%) and 1,10-phenanthroline (10 mol%) under aerobic conditions led to the formation of unsymmetric diaryl s

METHOD OF PREPARING CORE-SHELL COPPER NANOPARTICLES IMMOBILIZED ON ACTIVATED CARBON AND METHOD OF PREPARING CHALCOGENIDE COMPOUND USING NANOPARTICLES AS CATALYST

Disclosed herein is a method of preparing a Cu/Cu2O core-shell copper nanoparticle catalyst having high catalytic activity from [Cu3(BTC)2] and NaBH4 via a simple chemical reduction method. Also disclosed is a method of preparing a chalcogenide compound by using the nanoparticle catalyst as a heterogeneous catalyst in a cross-coupling reaction between a chalcogenide precursor compound and a boron-containing compound. The disclosed cross-coupling reaction is performed via a simple process, and the disclosed nanoparticle catalyst is compatible with various substrates under mild reaction conditions and exhibits excellent recyclability without a reduction in catalytic activity.

Peracetic acid mediated sp2 C-H selenation of arenes

Peracetic acid promoted C-Se coupling reaction of arenes with diselenides under metal-free and solvent-free conditions has been described. The resulting selenide ethers were obtained in good to excellent yields. Peracetic acid provided the selenide ethers

Copper nanoparticles catalyzed Se(Te)-Se(Te) bond activation: A straightforward route towards unsymmetrical organochalcogenides from boronic acids

A highly porous copper metal-organic framework, [Cu3(BTC)2] (BTC=benzene-1,3,5-tricarboxylate) was synthesized and used as a precursor for the synthesis of copper nanoparticles (NPs) and characterized by several techniques, including XRD, SEM, TEM, EDX and BET measurements. The as-synthesized copper nanoparticles were immobilized onto activated charcoal (AC) by means of ultrasonication at room temperature without any pretreatment. The Cu NPs/AC was employed as a heterogeneous catalyst for the cross-coupling of diphenyl diselenide and boronic acids to form diphenyl selenides through Se-Se bond activation under ligand-, base-, and additive-free conditions. The copper NPs/AC, which combines the architecture of MOFs and the high surface area of charcoal, could be an efficient heterogeneous catalytic system that is compatible with a variety of substituents on diphenyl selenides. Its promising catalytic activity relative to that of other homogeneous systems and low catalyst loading for the synthesis of unsymmetrical diaryl selenides is an important application in the area of nanocatalysis. The Cu NPs/AC catalyst, which exhibits excellent catalytic activity and remarkable tolerance to a wide variety of substituents, led to Se sp3-, sp2-, and sp-carbon bond formation by using DMSO as a solvent and atmospheric air as oxidant. This approach can also be extended to the preparation of unsymmetrical organotelluride derivatives. Three-in-one catalyst: Copper nanoparticles on activated charcoal show excellent catalytic activity towards the synthesis of unsymmetrical chalcogenides, starting from boronic acids, in air under ligand-, base-, and additive-free conditions, and resulting in selenium sp3-, sp2-, and sp-carbon bond formation.

Transition-metal-free synthesis of unsymmetrical diaryl chalcogenides from arenes and diaryl dichalcogenides

A transition-metal-free synthetic method has been developed for the synthesis of unsymmetrical diaryl chalcogenides (S, Se, and Te) from diaryl dichalcogenides and arenes under oxidative conditions by using potassium persulfate at room temperature. Variously substituted arenes such as anisole, thioanisole, diphenyl ether, phenol, naphthol, di- and trimethoxy benzenes, xylene, mesitylene, N,N-dimethylaniline, bromine-substituted arenes, naphthalene, and diaryl dichalcogenides underwent carbon-chalcogen bond-forming reaction to give unsymmetrical diaryl chalcogenides in trifluoroacetic acid. To understand the mechanistic part of the reaction, a detailed in situ characterization of the intermediates has been carried out by 77Se NMR spectroscopy by using diphenyl diselenide as the substrate. 77Se NMR study suggests that electrophilic species ArE+ is generated by the reaction of diaryl dichalcogenide with persulfate in trifluoroacetic acid. The electrophilic attack of arylchalcogenium ion on the arene may be responsible for the formation of the aryl-chalcogen bond.

Methods for formation of aryl-sulfur and aryl-selenium compounds using copper(I) catalysts

A mild, palladium-free synthetic protocol for the cross-coupling reaction of vinyl or aryl iodides and thiols or selenols using, in certain embodiments, 10 mol % CuI and 10 mol % neocuproine, with NaOt-Bu as the base, in toluene at 110 ° C. A variety of vinyl/aryl sulfides and vinyl/aryl selenides can be synthesized in excellent yields from readily available iodides and thiols or selenols.

A general method for the formation of diaryl selenides using copper(I) catalysts

We report a mild, palladium-free synthetic protocol for the cross coupling reaction of aryl iodides and phenyl selenol using 10 mol% CuI/neocuproine, NaOt-Bu or K2CO3 as base, in toluene, at 110°C. Using this protocol, we show that a variety of diaryl selenides can be synthesized in good yields from commercially available aryl iodides.