37985-11-8

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 622-47-9 4-tolylacetic acid 
• 96170-77-3 1,3-diethoxy-1-phenyl-4-p-tolyl-butane 
• 2378-86-1 4-methylbenzyltriphenylphosphonium bromide 
• 104-82-5 4-Methylbenzyl chloride 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 52147-97-4 trans 2-phenylethenesulfonyl chloride 
• 105654-27-1 (Z,Z)-bis(2-phenylethenyl)telluride 
• 139926-43-5 (E,E)-bis(2-phenylethenyl)telluride 
• 82296-87-5 [(Z)-2-(phenyltellanyl)vinyl]benzene 
• 110295-96-0 trans-styryl phenyl telluride 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 180906-68-7 (E,E)-4-phenyl-1-(4-methylphenylseleno)-1,3-butadiene 
• 100-34-5 benzene diazonium chloride 

Downstream Products

• 102478-08-0 cis-2-tolyl-5-phenyl-8-oxabicyclo<4.3.0>non-3-ene-7,9-dione 
• 37985-00-5 trans-1-(p-Tolyl)-4-phenylbut-2-en 
• 27331-34-6 1-(4-methylphenyl)naphthalene 
• 6936-14-7 1,2-dihydro-4-(4-methylphenyl)naphthalene 
• 29304-62-9 6-methyl-4-phenyl-1,2-dihydro-naphthalene 
• 19723-03-6 7-methyl-1-phenylnaphthalene 
• 52010-91-0 4-((1E,3E)-4-phenylbuta-1,3-dienyl)benzaldehyde 

Relevant academic research and scientific papers

A NOVEL SYNTHESIS OF (E,E)-1,4-DIARYL-1,3-BUTADIENES BY THE RUTHENIUM(II) CATALYZED REACTION OF (E)-2-ARYLETHENESULFONYL CHLORIDES WITH VINYLARENES

Symmetrical and unsymmetrical (E,E)-1,4-diaryl-1,3-butadienes can be prepared in high yields from (E)-2-arylethenesulfonyl chlorides by treating with vinylarenes in the presence of ruthenium(II) phosphine complex in benzene.

Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (E)-Stilbenes and (1 E,3 E)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products

A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The protocol can be extended to the synthesis of (1E,3E,5E)-1,6-diphenylhexa-1,3,5-triene in 40% yield. Products 5e, 5f, and 7a showed good photoluminescence quantum yields ranging from 72 to 99%.

Synthesis of stilbene derivatives via visible-light-induced cross-coupling of aryl diazonium salts with nitroalkenes using-NO2 as a leaving group

The straightforward visible-light-induced synthesis of stilbene compounds via the cross-coupling of nitroalkenes and diazonium tetrafluoroborates under transition-metal-free conditions is described. The protocol uses green LEDs as light sources and eosin Y as an organophotoredox catalyst. Broad substrate scope and exclusive selectivity for the (E)-configuration of stilbenes are observed. This protocol proceeds via a radical pathway, with nitroalkenes serving as the radical acceptor, and the nitro group is cleaved during the process.

Syntheses of p-terphenyls and 11,12-dihydroindeno[2,1-a]fluorene by one-pot benzannulation of Diels-Alder reactions of trans-1,2-dichloroethene and dienes

A series of substituted p-terphenyls and 11,12-dihydroindeno[2,1-a]fluorene were successfully synthesized by one-pot benzannulation of Diels-Alder reaction with 1,2-dichloroethene as an acetylene equivalent dienophile. Two chlorine atoms could be good leaving groups to easily undergo subsequent elimination reactions of Diels-Alder products at a high temperature.

Synthesis of 1,4-diarylbuta-1,3-dienes through palladium-catalyzed decarboxylative coupling of unsaturated carboxylic acids

It has been found that readily available hydroxylated cinnamic acids such as ferulic acid undergo palladium-catalyzed decarboxylative coupling with aryl iodides and internal alkynes in a 1:1:1 manner to produce 1,4-diarylbuta-1,3- dienes. The butadiene synthesis has also been achieved through the coupling of aryl halides with dienoic acids. Some of the products exhibit solid-state fluorescence.

Wittig reaction with ion-supported Ph3P

Ion-supported Ph3P, 4-(diphenylphosphino)benzyltrimethylammonium bromide A and N-methyl-N-[4-(diphenylphosphino)benzyl]pyrrolidinium bromide B, were used for the Wittig reaction. Ion-supported phosphonium salts A1 and B1, which were prepared from the reactions of ion-supported Ph3P A and B with ethyl bromoacetate, respectively, reacted with aromatic and aliphatic aldehydes in the presence of K2CO3 to give the corresponding α,β-unsaturated ethyl esters in good yields with high purity by simple filtration of the reaction mixture and subsequent removal of the solvent from the filtrate. Similarly, ion-supported phosphonium salts A2 and B2, which were prepared from the reactions of ion-supported Ph3P A and B with p-methylbenzyl bromide, respectively, reacted with aromatic and aliphatic aldehydes in the presence of NaH to provide the corresponding p-methylstyrene derivatives in good yields with high purity by simple filtration of the reaction mixture and the subsequent removal of the solvent from the filtrate. In both reactions, the co-product, ion-supported Ph3PO, could be obtained quantitatively by simple filtration, and was converted into the corresponding ion-supported Ph3P A and B again in high yields using dimethyl sulfate, followed by the reduction with LiAlH4. Recovered and regenerated ion-supported Ph3P A and B could be reused for the same Wittig reaction while maintaining good yields of ethyl (E)-3-(4′-chlorophenyl)-2-propenoate and 1-(4′-chlorophenyl)-2- (4″-methylphenyl)ethene with high purity by simple filtration and removal of the solvent from the filtrate.

Cyclic 1,1-bis(silyl)alkenes-new building blocks for the stereoselective synthesis of unsymmetrical (E)-stilbenes and (E,E)-1,4-diarylbuta-1,3-dienes

A new efficient synthetic protocol for the highly stereoselective synthesis of unsymmetrical (or symmetrical) (E)-stilbenes and (E,E)-1,4-diarylbuta-1,3-dienes based on sequential palladium-catalyzed Heck arylation-Hiyama cross-coupling reactions using cy

Catalysis by ionic liquids: Cyclopropyl carbinyl rearrangements catalyzed by [pmim]Br under organic solvent free conditions

Aryl substituted cyclopropyl carbinol derivatives undergo stereoselective rearrangements catalyzed by the ionic liquid, 1-methyl-3-pentylimidazolium bromide, under sonication, without any organic solvent, to produce the substituted conjugated all-trans-butadienes.

Indium triflate catalyzed rearrangement of aryl-substituted cyclopropyl carbinols to 1,4-disubstituted 1,3-butadienes

Aryl-substituted cyclopropyl carbinol derivatives undergo a facile stereoselective rearrangement catalyzed by In(OTf)3 in dichloromethane under sonication to produce the substituted conjugated all-trans-butadienes. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Stereoselective synthesis of (E,E)-1-arylselenobutadienes by cross- coupling reactions in the presence of palladium catalyst

Hydrozirconation of arylselenoethynes 1 gives selenium containing zirconium(IV) complexes 2, which are cross coupled with alkenyl halides in the presence of Pd (PPh3)4 to afford (E,E)-1-arylselenobutadienes 4 in high yields.