78808-28-3

Upstream product

• 591-50-4 iodobenzene 
• 1666-13-3 diphenyl diselenide 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 103-82-2 phenylacetic acid 
• 6274-57-3 (4-bromobenzyl)dimethylamine 
• 106-38-7 para-bromotoluene 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 4848-71-9 trimethylstannyl phenyl selenide 
• 2179-79-5 phenyl selenocyanate 

Downstream Products

• 19829-56-2 4,4'-dibromobibenzyl 
• 1666-13-3 diphenyl diselenide 
• 18255-05-5 benzyl phenyl selenide 
• 78808-34-1 9-anthrylmethyl phenyl selenide 

Relevant academic research and scientific papers

Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides

A new protocol was developed to synthesize (enantioenriched) thioethers and selenoethers from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These syntheses were promoted by the presence of weak base and did not require the use of any transition metal, and resulted in the target products with good to excellent yields (72-94%). Using quaternary ammonium salts synthesized from enantiomerically enriched amines led to highly enantiopure benzylic thioethers and selenoethers (94-99% ee) with configurations reversed from those of their enantioenriched quaternary ammonium salts. This journal is

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.

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.).

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.

Indium-mediated cleavage of diphenyl diselenide and diphenyl disulfide: efficient one-pot synthesis of unsymmetrical diorganyl selenides, sulfides, and selenoesters

A convenient and efficient method was developed for the synthesis of alkyl phenyl selenides, sulfides, and selenoesters in one-pot reaction by using indium metal. The reaction showed the selectivity for tert-alkyl, benzylic, and allylic halides over primary and secondary alkyl halides. For the reaction of primary and secondary alkyl iodides and bromides, the yields of selenides were improved by the addition of a catalytic amount of iodine.

Indium-mediated mild and efficient one-pot synthesis of alkyl phenyl selenides

A mild and convenient one-pot process for synthesizing alkyl phenyl selenides is developed using indium metal. The reaction shows the selectivity for tert-alkyl, benzylic, and allylic halides over primary and secondary alkyl halides.

Employment of palladium pincer-complexes in phenylselenylation of organohalides

Palladium pincer-complex-catalyzed selenylation of propargyl-, allyl-, benzyl-, and benzoyl halides could be achieved under mild reaction conditions employing trimethylstannylphenylselenide as selenylating agent. This reaction has a high functional group

Flash Pyrolysis of Selenides. Syntheses of Bibenzyls, Olefins, and Related Compounds

Pyrolyses of a series of selenides and diselenides were studied. Selenides and diselenides bound with an active methylene group like benzyl gave a variety of substituted bibenzyls and related ethane derivatives in high yields. Other diselenides were easily caused to cleave to give various aromatic and aliphatic olefins in good yields together with elemental selenium. Lepidopterene, paracyclophane, and benzocyclobutene were prepared by thermal cleavage of their corresponding phenylselenomethyl-substituted compounds as an application of the pyrolysis concerned.