105654-27-1

Upstream product

• 588-73-8 (Z)-β-bromostyrene 
• 536-74-3 phenylacetylene 
• 12034-41-2 disodium telluride 
• 100-52-7 benzaldehyde 

Downstream Products

• 120609-16-7 (Z)-1,1,3-Triphenyl-2-propen-1-ol 
• 131025-95-1 3-<(Z)-2-phenyl-1-ethenyl>cyclohexanone 
• 62839-72-9 (Z)-1-(dec-1-enyl)benzene 
• 1566-67-2 (Z)-styryl acetate 
• 1566-65-0 cinnamylacetate 
• 127084-19-9 1-((Z)-Styryl)-cyclohexanol 
• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 
• 5808-05-9 (1Z,3E)-1,4-diphenylbuta-1,3-diene 
• 5807-76-1 (1Z,3Z)-1,4-diphenylbuta-1,3-diene 
• 62839-70-7 (2Z)-1,3-diphenyl-2-propen-1-ol 
• 144758-31-6 (Z)-6-phenylhex-5-en-2-one 
• 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 
• 27331-24-4 1-(4Methylphenyl)-4-Phenylbuta-1,3-diene 

Relevant academic research and scientific papers

Green hydroselenation of aryl alkynes: Divinyl selenides as a precursor of resveratrol

A simple and efficient protocol to prepare divinyl selenides has been developed by the regio- and stereoselective addition of sodium selenide species to aryl alkynes. The nucleophilic species was generates in situ, from the reaction of elemental selenium with NaBH4, utilizing PEG-400 as the solvent. Several divinyl selenides were obtained in moderate to excellent yields with selectivity for the (Z,Z)-isomer by a one-step procedure that was carried out at 60°C in short reaction times. The methodology was extended to tellurium, giving the desired divinyl tellurides in good yields. Furthermore, the Fe-catalyzed cross-coupling reaction of bis(3,5-dimethoxystyryl) selenide 3f with (4-methoxyphenyl)magnesium bromide 5 afforded resveratrol trimethyl ether 6 in 57% yield.

Stereoselective synthesis of enynes by nickel-catalyzed cross-coupling of divinylic chalcogenides with alkynes

(Z,Z)- and (E,E)-divinylic selenides and telurides undergo direct coupling with terminal alkynes in the presence of a nickel/CuI catalyst at room temperature to give (Z)- and (E)-enyne systems in good yields and with complete retention of configuration.

Preparation of symmetrical divinyl tellurides via an ylidation reaction

Symmetrical divinyl tellurides are prepared by sequential reaction of bis-(triphenylmethyl phosphonium) halotellurate with base or by the reaction of triphenylmethylidene phosphoranes with TeCl4, followed by aldehydes. The products are converted to E-α,β-unsaturated aldehydes by treatment with n-BuLi and DMF.

Styryl coupling vs. styryl acetate formation in reactions of styryl tellurides with palladium(II) salts

In sharp contrast to the expected formation of a telluride-palladium complex, the treatment of either (E,E)- and (Z,Z)-distyryl tellurides (1 and 2) or (E)- and (Z)-styryl phenyl tellurides (5 and 6) with Li2PdCl4 in acetonitrile at 25 deg C results in the formation of stereoisomeric 1,4-diphenylbuta-1,3-dienes, whereas the treatment of 1 and 2 with Pd(OAc)2 produces styryl acetates solely or mainly.

REACTIONS OF SELENIUM AND TELLURIUM METALS WITH PHENYLACETYLENE IN THREE-PHASE CATALYTICAL SYSTEMS

Compounds 2, 6a-d, 7, 8 were prepared in three-phase catalytical systems using selenium and tellurium metals as one phase.A radical anion chain mechanism is proposed in the reaction of tellurium metal with phenylacetylene.

REACTION OF TELLURIUM WITH PHENYLACETYLENE: A REINVESTIGATION

The reaction of powdered tellurium with phenylacetylene under strongly basic conditions yields cis and trans-2,6-diphenyl-1,4-ditellurafulvenes, rather than Z and E isomers of a five-membered cyclic ditelluride, as recently reported.