18255-12-4

Upstream product

• 18255-05-5 benzyl phenyl selenide 
• 644-36-0 o-methylphenylacetic acid 
• 1666-13-3 diphenyl diselenide 
• 591-50-4 iodobenzene 
• 552-45-4 1-chloromethyl-2-methylbenzene 
• 95-47-6 o-xylene 
• 89-92-9 2-methylbenzyl bromide 
• 100-44-7 benzyl chloride 
• 152407-19-7 (2-Methoxyethoxy)methyl phenyl selenide 
• 108-88-3 toluene 
• 75772-14-4 benzylmethylphenylselenonium tetrafluoroborate 

Relevant academic research and scientific papers

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.).

A highly efficient heterogeneous ruthenium(III)-catalyzed reaction of diaryl diselenides with alkyl halides leading to unsymmetrical diorganyl selenides

A highly efficient heterogeneous ruthenium(III)-catalyzed reaction of diaryl diselenides with alkyl halides was achieved in DMF at 100?°C in the presence of 2?mol% of an MCM-41-immobilized bidentate nitrogen ruthenium(III) complex [MCM-41-2N-RuCl3] and zinc, yielding a variety of unsymmetrical diorganyl selenides in good to excellent yields. This new heterogeneous ruthenium catalyst can easily be prepared via a simple two-step procedure from commercially readily available and inexpensive reagents, and recovered by filtration of the reaction solution and recycled for at least eight times without a significant loss of activity.

Metal-free sp3 C-H functionalization: A novel approach for the syntheses of selenide ethers and thioesters from methyl arenes

A DTBP-promoted metal-free and solvent-free formation of C-Se and C-S bonds through sp3 C-H functionalization of methyl arenes with diselenides and disulfides is described. the Partner Organisations 2014.

Zn in ionic liquid: An efficient reaction media for the synthesis of diorganyl chalcogenides and chalcogenoesters

A straightforward and efficient methodology is described to synthesize structurally diverse diorganyl selenides, sulfides, seleno- and thioesters by using commercially available Zn dust in ionic liquid. Excellent yields were achieved under neutral conditions at room temperature in a short time. The solvent/ionic liquid is reusable and exhibited higher performance as compared with organic solvents.

Bimetallic system for the synthesis of diorganyl selenides and sulfides, chiral β-seleno amines, and seleno- and thioesters

The bimetallic reagent Sn(II)/Cu(II) in [bmim]BF4 was efficiently used for the cleavage of diaryl diselenides and disulfides and reacts with a variety of organic substrates, such as organic halides, acid chlorides, and β-amino mesylates affording the diorganyl selenides and sulfides within very short reaction times, under mild conditions and with excellent yields, using BMIM-BF4 as a reusable solvent.

Synthesis of diorganyl selenides mediated by zinc in ionic liquid

Figure presented A new approach for the synthesis of diorganyl selenides is described. By using economically attractive zinc dust in BMIM-BF4, a series of diorganyl selenides were efficiently achieved in excellent yields, under neutral reaction conditions. Compared to the usual organic solvents, BMIM-BF4 exhibited higher performance with the advantage to be reused up to five successive runs.

Ionic liquid: An efficient and recyclable medium for synthesis of unsymmetrical diorganyl selenides promoted by InI

In an environmentally friendly protocol, InI was used as a reducing agent for the Se-Se bond to prepare unsymmetrical diorganyl selenides with very short reaction times, mild conditions and excellent yields using (bmim)BF4 as a recyclable solvent.

A New Method of Generation of α-Selenocarbenium Ions from Se,O-Heteroacetals and Their Reactions

Various Se,O-heteroacetals were prepared by the LiAlH4 reduction of diselenides 1 followed by alkylation with methoxymethyl chloride or (2-methoxyethoxy)methyl (MEM) chloride.Olefinic and acetylenic α-seleno carbenium ions were generated by the selective C-O bond cleavage of O-(2-methoxyethyl)-Se,O-heteroacetals with titanium(IV) chloride and cyclized to give the seleno heterocyclic compounds.Olefinic MEM-selenides 3a,b,d-f,h underwent the endo-mode cyclization to afford 4-chloroselenacycloalkanes 4a,b,d-f,h in good yields, whereas acetylenic MEM-selenides 12b-e,g-j underwent the exo-mode cyclization to give 3-(1-chloroalkylidene)selenacycloalkanes 13b-e,g-j.This new utilization of α-seleno carbenium ions was also applied to the intramolecular and intermolecular Friedel-Crafts reactions.

Sigmatropic Rearrangement of Ylides Derived from Benzylic Selenonium Salts

The sigmatropic rearrangement of a series of ylides derived from benzylic selenonium salts has been observed.These ylides alkyl or aryl o-methylbenzyl selenides.The competition between nucleophilic displacement and ylide formation in the reaction of base with benzylic selenonium salts has been evaluated.

Base Treatment of Benzylic Selenonium Salts. Sigmatropic Rearrangements vs. Nucleophilic Displacement

Treatment of certain benzylic selenonium salts with a variety of bases resulted in nucleophilic attack to yield either an alkylation or a benzylation of the base, while the use of sodium amide in liquid ammonia as base generated a selenonium ylide which gave ortho substitution of the benzyl group via sigmatropic rearrangement.