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Upstream product

• 108-37-2 1-bromo-3-chlorobenzene 
• 63503-60-6 3-chlorophenylboronic acid 
• 625-99-0 3-iodochlorobenzene 
• 108-42-9 3-chloro-aniline 
• 32111-96-9 1-chloro-3-selenocyanatobenzene 

Downstream Products

• 1258866-39-5 1,5-bis(3-chlorophenyl)-2,4-diaza-1,5-diselena-3-thia-2,3-pentadiene 

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.

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.

Iron(III)-catalyzed synthesis of selenoesters from α-amino carbonyl derivatives at room temperature

An Fe(III)-catalyzed efficient method has been developed for the synthesis of selenoester derivatives in high yields through the coupling of α-amino carbonyl/glycine derivatives and diselenides under ambient air. A library of benzoselenoate derivatives having a variety of substituents has been synthesized. A plausible reaction pathway has been predicted. Experimental results suggest that the reaction proceeds through a radical pathway. Operational simplicity, compatibility with various α-amino carbonyls and diselenides, high yields, fast reaction and mild reaction conditions are the notable advantages of this procedure. We have also shown the practical application of the synthesized selenoesters which is useful to generate peptide bonds in biological sciences.

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.

Preparation method for diphenyl diselenium compound

The invention discloses a preparation method for a diphenyl diselenium compound. According to the method, an arylboronic acid compound and elemental selenium serve as reaction raw materials, an organic solvent serves as a reaction solvent, under the effect of a silver catalyst, reaction is carried out so as to obtain the diphenyl diselenium compound, the reaction temperature is 100-140 DEG C, thereaction equation is shown in the specification, wherein R is a benzene ring, a naphthalene ring, a heterocyclic ring or a substituted benzene ring. The method has the beneficial effects that the tolerance of functional groups of substrates is high, and the range of the substrates is wide; and the raw materials and the catalyst are cheap and easily available, the conditions are mild, the post-treatment is simple, the yield and purity of a product are high, and the method is suitable for large-scale industrial production.

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.).

The first observation of the E,Z configuration of Ar-X-N=S=N-X-Ar (X = S, Se) chains in the crystalline state

New oligomeric analogues of poly(sulfur nitride), i.e. 3-ClC 6R4-X-N=S=N-X-C6R4Cl-3 (5-8; R = H, F and X = S, Se), were synthesized and structurally characterized in the solid state by single-crystal XRD, in solution by variable-temperature NMR spectroscopy and in the gas phase with DFT/B3LYP calculations. In the crystal, compounds 5-7 display the well-known Z,Z configuration, whereas 8 (R = F, X = Se) is the first compound to display the E,Z configuration amongst twelve structurally defined Ar-X-N=S=N-X-Ar (X = S, Se) derivatives in the hydrocarbon and fluorocarbon series. Through a careful analysis of the packing schemes and the intermolecular interactions of the various compounds, an explanation of the abnormal behaviour of 8 is put forward. The unique E,Z configuration of the title compounds in the crystal is observed for Ar = 3-ClC6F 4 and X = Se - in the presence of eleven Z,Z configurations found by XRD for various Ar and X groups in the hydrocarbon and fluorocarbon series - and explained by specific intermolecular Se???Cl and F???Cl interactions. (Colour code: grey - C, green - Cl, light green - F, blue- N, orange - S, magenta - Se.)