105230-62-4

Upstream product

• 32111-96-9 1-chloro-3-selenocyanatobenzene 
• 591-51-5 phenyllithium 
• 60-29-7 diethyl ether 
• 1666-13-3 diphenyl diselenide 
• 36229-42-2 (3-chlorophenyl)magnesium bromide 
• 71-43-2 benzene 
• 34837-55-3 Phenylselenyl bromide 
• 63503-60-6 3-chlorophenylboronic acid 
• 456-39-3 3-chlorobenzenediazonium tetrafluoroborate 
• 645-96-5 Benzeneselenol 
• 625-99-0 3-iodochlorobenzene 
• 2312-23-4 m-chlorophenylhydrazine hydrochloride 
• 52251-58-8 lithium phenylselenide 
• 105230-47-5 (3-chlorophenyl)azo 4-methylphenyl sulfone 

Downstream Products

• 127764-11-8 dichloro-(3-chloro-phenyl)-phenyl-λ⁴-selane 

Relevant academic research and scientific papers

C-Se cross-coupling of arylboronic acids and diphenyldiselenides over non precious transition metal (Fe, Cu and Ni) complexes

Various tetradentate and tridentate ligands such as salophane, bishydrazone, bisbenzimidazolyl pyridine and isonicotinohydrazide have been prepared. Transition metal complexes of these ligands with Cu, Ni and Fe have been further synthesized and characterized by UV–vis, IR, NMR and CHN analysis. Catalytic activity of the metal complexes was tested for the cross coupling of diarylchalcogenide with arylboronic acid in DMSO as solvent in presence of a base. These non-precious metal complexes catalysed cross coupling reactions smoothly in shorter reaction time compared to earlier reports with comparable yields.

New routes for the synthesis of unsymmetrical diarylselenides: Effect of heat, light and ultrasound

Herein, we report the photochemical coupling of diphenyldiselenides with substituted phenylhydrazine hydrochloride without catalyst. The protocol was developed not only in presence of sunlight and UV light but also under thermal condition for comparison study. Moreover, ultrasound assisted new catalytic protocol was developed using Ni(II)/L-proline system in DMSO with the advantage of shorter reaction time compared to earlier reports. We have also developed a new C-Se cross coupling reaction where phenylselenyl chloride and arylhydrazine hydrochlorides were effectively coupled using developed catalytic system.

Photocatalyst-free photoredox synthesis of diaryl selenides by reaction of diselenides with aryldiazo sulfones

A photcatalyst-free photoredox synthesis of diaryl selenides has been developed by coupling reaction of diselenides with aryldiazo sulfones. The reaction was accelerated under visible light irradiation without using a photocatalyst or photosensitizer. This approach facilitates the synthesis of diaryl selendes with a wide range of functional group tolerance.

Atom-Economical Synthesis of Unsymmetrical Diaryl Selenides from Arylhydrazines and Diaryl Diselenides

An atom-economical method for the synthesis of unsymmetrical diaryl selenides from arylhydrazines and stoichiometric amounts of diselenides was developed under mild conditions. The new and facile selenide synthesis involved the use of an inexpensive base in air to form unsymmetrical diaryl selenides in good yields. This C–Se radical arylation of diaryl diselenides was performed by forming aryl radicals from arylhydrazines under oxidative conditions. The formation of a phenyl radical was supported by trapping with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) in air. Therefore, this synthesis might involve a homolytic aromatic substitution (HAS) mechanism. The synthesis is both low costing and environmentally friendly and, therefore, may be useful for the practical synthesis of unsymmetrical diaryl selenides.

Trichloroisocyanuric Acid-Promoted Synthesis of Arylselenides and Aryltellurides from Diorganyl Dichalcogenides and Arylboronic Acids at Ambient Temperature

A transition-metal-free method for the synthesis of arylselenides and aryltellurides has been established based on the oxidative cross-coupling between diorganyl dichalcogenides and aryl boronic acids. With trichloroisocyanuric acid as an oxidant, the reaction proceeded smoothly to afford the desired products in 45–97% yields at ambient temperature. Three reaction reagents used in this method are stoichiometric and the oxidation by-product isocyanuric acid can be easily isolated and recovered. Besides of arylboronic acids, aryl trifluoroborates and aryl trihydroxyborates salts are also able to perform this transformation. (Figure presented.).

Method for preparing asymmetric organic selenium ether compounds through metal-free chemical oxidation method (by machine translation)

The method is mild in reaction condition, convenient to operate, high in 1 reaction condition, convenient 2 to operate, high in safety, wide in substrate range, high 2 - 8h in yield, particularly suitable for reaction of various poor 3 electric and sterically hindered arylboronic acid and diselenoxy ether, and capable of finishing most of the reaction 4h. (by machine translation)

Efficient heterogeneous copper-catalysed C–Se coupling of aryl iodides with symmetrical diselenides towards unsymmetrical monoselenides

A highly efficient heterogeneous copper(I)-catalysed C–Se coupling of aryl iodides with diaryl diselenides was achieved in dimethylformamide at 110 °C under neutral conditions by using a 10 mol% of bipyridine-functionalised MCM-41-supported copper(I) complex [bpy-MCM-41-CuI] as the catalyst and magnesium as the reductive reagent, yielding a variety of unsymmetrical diaryl selenides in good to excellent yields. This heterogeneous copper catalyst can be easily recovered by a simple filtration of the reaction solution and recycled at least seven times without significant loss of activity.

Simple and catalyst-free method for the synthesis of diaryl selenides by reactions of arylselenols and arenediazonium salts

We describe here a simple and catalyst-free method to synthesize diaryl selenides by reaction of arenediazonium tetrafluoroborate salts with arylselenols, generated in situ by using diaryl diselenides and hypophosphorous acid (H3PO2), using THF as solvent. This is a direct nucleophilic aromatic substitution (SNAr) reaction performed with diaryl diselenides and arenediazonium salts bearing electron-withdrawing and electron-donating groups affording the corresponding diaryl selenides in moderated to good yields.

Simple and catalyst-free method for the synthesis of diaryl selenides by reactions of arylselenols and arenediazonium salts

We describe here a simple and catalyst-free method to synthesize diaryl selenides by reaction of arenediazonium tetrafluoroborate salts with arylselenols, generated in situ by using diaryl diselenides and hypophosphorous acid (H3PO2), using THF as solvent. This is a direct nucleophilic aromatic substitution (SNAr) reaction performed with diaryl diselenides and arenediazonium salts bearing electron-withdrawing and electron-donating groups affording the corresponding diaryl selenides in moderated to good yields.

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.