69447-35-4

Upstream product

• 694-80-4 2-bromo-1-chlorobenzene 
• 615-41-8 2-iodochlorobenzene 
• 858495-97-3 2-chloro-benzeneseleninic acid 

Downstream Products

• 858495-97-3 2-chloro-benzeneseleninic acid 
• 1159428-84-8 C₁₅H₁₆ClNSe 
• 1169496-99-4 Se-2-chlorophenyl selenobenzoate 
• 1448621-22-4 (S)-5-((2-chlorophenylselanyl)methyl)pyrrolidin-2-one 

Relevant academic research and scientific papers

Clarification on the reactivity of diaryl diselenides toward hexacyclohexyldilead under light

In this study, the reactivity of organochalcogen compounds toward a representative alkyl-lead bond compound under light was investigated in detail. Under light irradiation, the Cy-Pb bond of Cy6 Pb2 (Cy = cyclohexyl) undergoes homolytic cleavage to generate a cyclohexyl radical (Cy?). This radical can be successfully captured by diphenyl diselenide, which exhibits excellent carbon-radical-capturing ability. In the case of (PhS)2 and (PhTe)2, the yields of the corresponding cyclohexyl sulfides and tellurides were lower than that of (PhSe)2. This probably occurred due to the low carbon-radical-capturing ability of (PhS)2 and the high photosensitivity of the cyclohexyl-tellurium bond.

Highly selective radical isothiocyano-chalcogenization of alkenes with NH4SCN in water

In the presence of catalytic amounts of molecular iodine and stoichiometric potassium persulfate, a green, highly chemoselective, regioselective and cis-selective radical isothiocyano-chalcogenization of alkenes with NH4SCN in water is disclosed. This three component reaction features high selectivities, an environmentally benign process, mild conditions, high yields, excellent functional-group tolerance, and broad substrate scope. The resulting products can be further transformed into other molecules with structural similarities of these compounds to bioactive analogs.

FeCl3-catalyzed three-component aryl-selenylation of alkenes

FeCl3-catalyzed three-component aryl-selenylation of alkenes with good to excellent yields has been disclosed. This method is characterized by synthesis of complicated products in a single-step reaction, simple operation and readily available commercially reagents. Finally, a reasonable mechanism of FeCl3-catalyzed aryl-selenylation is proposed.

Visible-light-driven radical 1,3-addition of selenosulfonates to vinyldiazo compounds

Herein, we report a visible-light-driven radical 1,3-selenosulfonylation of vinyldiazo compounds with selenosulfonates, providing various γ-seleno allylic sulfones in good yields. This photochemical reaction was carried out at room temperature in an open flask using ethyl acetate as the solvent without any photocatalysts or additives. The control experiments corroborated that the 1,3-addition proceeded via a radical-chain propagation process. The synthetic applications of the resulting products were demonstrated by deselenization, reduction, bromination and allylation.

Continuous Electrochemical Synthesis of Iso-Coumarin Derivatives from o-(1-Alkynyl) Benzoates under Metal- and Oxidant-Free

A non-oxidant and metal-free strategy for synthesizing iso-coumarin by using a continuous electrochemical microreactor to initiate an oxidative cyclization reaction of o-(1-alkynyl) benzoate and radicals. This efficient and clean continuous electrosynthesis method not only avoids the complicated gas protection operation and production of by-products in the batch processes, but also help to overcome the difficulty that batch metal catalysis and electrocatalysis are difficult to scale up, and has the potential for pilot-scale experiment.

Metal-free difunctionalization of alkynes to access tetrasubstituted olefins through spontaneous selenosulfonylation of vinylidene: Ortho -quinone methide (VQM)

A metal-free difunctionalization of alkynes to access tetrasubstituted olefins through spontaneous selenosulfonylation of vinylidene ortho-quinone methide (VQM) was described herein. The reaction was conducted under mild conditions without any catalysts or additives. Preliminary mechanism studies revealed that the formation of VQM was the key for this alkyne di-functionalization reaction. The reaction could be applied in the enantioselective asymmetric synthesis of axially chiral styrene. Furthermore, the selenosulfonylation adducts can be transformed into useful naphtho[2,1-b]furan and benzofuran scaffolds.

Rhodium-Catalyzed Carbene Transfer Reactions for Sigmatropic Rearrangement Reactions of Selenium Ylides

The rearrangement of selenium ylides is even today almost unexplored, although it would provide access to important organoselenium compounds with broad downstream applications. In this report, the first systematic study of sigmatropic rearrangement reactions of selenium ylides using a simple rhodium catalyst with catalyst loadings as low as 0.01 mol % is described. Selenium oxide pyrolysis of the rearrangement products gives access to important 1,1-disubstituted butadienes.

Three-Component Aminoselenation of Arynes

The three-component coupling of tertiary amines, arynes, and aryl selenium bromide or diaryl diselenide as an electrophilic selenium source allowing the synthesis of 2-selanyl aniline derivatives is reported. This aminoselenation reaction of arynes installs a C-N and C-Se bond under mild conditions, and the products are formed in moderate to good yields. This reaction is compatible with various functional groups, and the preliminary studies on the mechanism of the reaction is also provided.

Regioselective Synthesis of Selenide Ethers through a Decarboxylative Coupling Reaction

An efficient and selective approach to the synthesis of selenide ethers containing one or two geminal C–Se bonds from readily available diselenides and phenylacetic acids was developed. Compounds containing one C–Se bond were prepared by employing air as the oxidant under metal-free conditions, whereas compounds having two geminal C–Se bonds were formed via the iron(III) chloride/oxygen/cesium carbonate (FeCl3/O2/Cs2CO3) system. Moreover, 1,2-diphenyldisulfane also could be smoothly converted into the corresponding sulfur ether product under the standard reaction conditions. (Figure presented.).

An efficient one-pot synthesis of symmetrical diselenides or ditellurides from halides with CuO nanopowder/Se0 or Te0/base

(Equation Presented). A CuO nanopowder-catalyzed coupling reaction of aryl, alkyl, and heteroaryl iodides with elemental selenium and tellurium takes place in the presence of KOH at 90 °C in DMSO. A wide range of substituted symmetrical diselenides and ditellurides were afforded with good to excellent yields.