82296-87-5

Upstream product

• 32294-60-3 diphenyl ditelluride 
• 588-73-8 (Z)-β-bromostyrene 
• 95849-68-6 α-chloromethyl phenyl telluride 
• 100-52-7 benzaldehyde 
• 536-74-3 phenylacetylene 
• 588-72-7 [(E)-2-bromoethenyl]benzene 

Downstream Products

• 15325-54-9 (Z)-hex-1-en-1-ylbenzene 
• 6111-82-6 (E)-1-phenyl-1-hexene 
• 104-51-8 1-butylbenzene 
• 19713-73-6 methyl (2Z)-3-phenylprop-2-enoate 
• 92-52-4 biphenyl 
• 103-26-4 Methyl cinnamate 
• 140-10-3 (E)-3-phenylacrylic acid 
• 140-10-3 cis-cinnamic acid 
• 65-85-0 benzoic acid 
• 4714-21-0 E-1-methyl-4-styryl-benzene 
• 37985-11-8 (E,E)-1-(4-methylphenyl)-4-phenylbuta-1,3-diene 
• 101552-30-1 1-Methyl-4-((1E,3Z)-4-phenyl-buta-1,3-dienyl)-benzene 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 

Relevant academic research and scientific papers

DES as a green solvent to prepare 1,2-bis-organylseleno alkenes. Scope and limitations

We describe here our results on the use of choline chloride/urea 1:2 as a deep eutectic solvent (DES) in the synthesis of vinyl selenides. A good selectivity for the (E)-1,2-bis-organylseleno alkenes was observed starting from terminal alkynes and diaryl

Glycerol/CuI/Zn as a recyclable catalytic system for synthesis of vinyl sulfides and tellurides

A convenient approach to the Cu-catalyzed coupling of diphenyl disulfide and diphenyl ditelluride with vinyl bromides using a recyclable catalytic system and glycerol as a green solvent is described. This protocol was efficiently used in the preparation of vinyl sulfides and vinyl tellurides with a variety of substituents in good yields and stereoselectively. The solvent/catalyst system was directly reused for four cycles without loss of activity.

Cerium(III)-mediated efficient and steroselective hydrochalcogenation of terminal alkynes

Vinylic chalcogenides were synthesized stereospecifically by hydrochalcogenation of propargylic amines or alcohols mediated by cerium(III) chloride. The products were obtained in good yields and with high regio- and stereoselectivities. Georg Thieme Verla

A simple and general preparation of vinylic sulfides, selenides and tellurides

A general method for the synthesis of vinylic chalcogenides by nucleophilic and Ni-catalyzed vinylic substitution on vinylic halides by phenyl chalcogenolates is described. The reactions were regio and stereoselective for the nickel catalyzed substitution

A simplified preparation of vinyl sulfides, selenides and tellurides by a Wittig-type reaction

The preparation of several vinyl sulfides, selenides and tellurides by Wittig-type reaction in a one-pot procedure is described. The chalcogenyl triphenylphosphoranes 3 are formed 'in situ' by the reaction of chloromethyl phenyl chalcogenide, potassium tert-butoxide and triphenylphosphine. Reaction of 3 with carbonyl compounds affords the vinyl chalcogenides 6-9 with preferential Z-configuration.

Tellurium in organic synthesis. Preparation of Z-vinylic cuprates from Z-vinylic tellurides and their reaction with enones and epoxides

Z-Vinylic tellurides, obtained with 100% stereoselectivity by the hydrotelluration of acetylenes, are easily transformed into Z-vinylic higher order cyanocuprates by reaction with preformed Me2-Cu(CN)Li2, W-Bu2Cu(CN)Lisub

CARBONYLATION OF ARYL- AND VINYL-TELLURIUM COMPOUNDS WITH CARBON MONOXIDE IN THE PRESENCE OF PALLADIUM(II) SALTS

Aryl- and vinyl-tellurium(II or IV) compounds react with carbon monoxide (CO) in suitable organic solvents to give the corresponding carboxylic acids in moderate to quantitative yields in the presence of a stoichiometric amount of a palladium(II) salt.Treatment of (Z)-styrylphenyl telluride with atmospheric pressure of CO at room temperature in the presence of palladium(II) chloride or lithium chloropalladate(II) affords predominantly (E)-cinnamic acid, while in the presence of palladium(II) acetate similar reaction gives the (Z)-acid highly selectively.Under higher CO pressures (5-50 atm), however, the (Z)-acid becomes the major product, even when palladium(II) chloride is used.The following pathways are proposed for this carbonylation: (1) in the first step organotellurium compounds form the monomeric and/or dimeric palladium complexes such as 2 and/or (R2Te)2PdCl2 (R = aryl, vinyl), then (2) the migration of R moiety from tellurium to palladium (transmetallation) occurs to afford the reactive aryl- or alkenyl-palladium compounds, and (3) the compounds react with CO to give the corresponding acylpalladium compounds, after alkaline hydrolysis, the carboxylic acids are formed.The presence of an ionic carbene-like organopalladium complex is proposed for the formation of the (E)-acid from (Z)-telluride.

PHOSPHINE-NICKEL(II), -COBALT(II), -PALLADIUM(0) AND -PALLADIUM(II) COMPLEXES AS CATALYSTS IN CROSS-COUPLING REACTIONS OF ARYL- AND ALKYL-GRIGNARD REAGENTS WITH ORGANIC TELLURIDES

Some alkyl- and aryl-tellurides react with Grignard reagents (RMgBr; R = aryl and alkyl) in the presence of NiCl2(PPh3)2, NiCl2(Ph2PCH2CH2CH2PPh2), or CoCl2(PPh3)2 as catalyst in THF or diethyl ether as solvent to give the cross-coupling products together with the homo-coupling products of the tellurides in good to moderate yields, with elemental tellurium being formed as a black precipitate.A catalytic reduction-oxidation cycle involving a Ni or Co complex bearing an organotellurium moiety (RTe; R = alkenyl, aryl, and alkyl) is proposed for the reaction.Palladium catalysts such as Pd(PPh3)4, PdCl2(PPh3)2, and PdCl2(PhCN)2 are revealed to be much less effective than the Ni and Co catalysts in both the yield and the stereoselectivity of the product.

Ni(II)- AND Co(II)-PHOSPHINE COMPLEX CATALYZED CARBON-CARBON BOND FORMATION BETWEEN ORGANIC TELLURIDES AND GRIGNARD REAGENTS

Treatment of alkenyl and aryl tellurides with Grignard reagents in the presence of NiCl2(PPh3)2, NiCl2(Ph2PCH2CH2CH2PPh2), or CoCl2(PPh3)2 as catalyst affords the cross-coupling products together with the homo-coupling products of the tellurides in good to moderate yields under mild conditions.