23637-43-6

Upstream product

• 100-42-5 styrene 
• 117892-78-1 1-phenylpropene-2-sulfonyl chloride 
• 873-66-5 1-propenylbenzene 
• 52147-97-4 trans 2-phenylethenesulfonyl chloride 
• 591-50-4 iodobenzene 
• 68036-69-1 (E)-2-methyl-4-phenyl-1,3-butadiene 
• 88888-14-6 C₁₈H₃₆N₃⁽³⁺⁾*2CHI₃*3I^(1-) 
• 1896-62-4 (E)-benzalacetone 
• 6921-34-2 benzylmagnesium chloride 
• 108-86-1 bromobenzene 
• 78-79-5 isoprene 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 15174-47-7 α-methyl-trans-cinnamaldehyde 
• 101-39-3 2-methyl-3-phenyl-2-propenal 

Relevant academic research and scientific papers

Etudes sur les composes organometalliques. Selectivite de l'addition 1,4 de composes benzyliques du titane IV avec la benzylideneacetone

Tetrabenzyltitanium and dialkoxybenzyltitanium compounds give essentially 1,4-addition with trans-4-phenyl-3-buten-2-one.

Synthesis of 1,3-disubstituted cyclohexenes from dienylethers: Via sequential hydrozirconation/deoxygenative cyclisation

Access to 1,3-disubstituted cyclohexenes from zirconocenes containing a latent electrophilic allylic fragment is described. Requiring a specific conformation, 6-endo-trig cyclisation is based on the TMSOTf-mediated generation of a stabilized carbocation.

Alkenylation of C(sp3)?H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts

α-Vinylation of phosphonates, phosphine oxides, sulfones, sulfonamides, and sulfoxides has been achieved by selective C?H zincation and copper-catalyzed C(sp3)?C(sp2) cross-coupling reaction using vinylphenyliodonium salts. The vinylation transformation proceeds in high efficiency and stereospecificity under mild reaction conditions. This zincative cross-coupling reaction represents a general alkenylation strategy, which is also applicable for α-alkenylation of esters, amides, and nitriles in the synthesis of β,γ-unsaturated carbonyl compounds.

Highly stereoselective synthesis of 2-methyl-1,3-dienes by palladium-catalyzed cross-coupling reaction with trimethylaluminum

Palladium-catalyzed cross-coupling reaction using tricyclohexylphosphine can be used to convert a range of 2-bromo-1,3-dienes efficiently and selectively to the corresponding methyl-branched conjugated dienes. Georg Thieme Verlag Stuttgart New York.

Catalyst-controlled regioselectivity in the synthesis of branched conjugated dienes via aerobic oxidative heck reactions

Pd-catalyzed aerobic oxidative coupling of vinylboronic acids and electronically unbiased alkyl olefins provides regioselective access to 1,3-disubstituted conjugated dienes. Catalyst-controlled regioselectivity is achieved by using 2,9-dimethylphenanthroline as a ligand. The observed regioselectivity is opposite to that observed from a traditional (nonoxidative) Heck reaction between a vinyl bromide and an alkene. DFT computational studies reveal that steric effects of the 2,9-dimethylphenanthroline ligand promote C-C bond formation at the internal position of the alkene.

Cobalt-catalyzed regio- and stereoselective intermolecular enyne coupling: An efficient route to 1,3-diene derivatives

The reaction of alkynes with vinyl arenes or vinyl trimethyl silane in the presence of a cobalt(II) complex, Zn and ZnI2 in CH 2Cl2 at rt to 50 °C provides 1,3-dienes in good to excellent yields. The Royal Society of Chemistry 2010.

Regioselective 1,4-addition of ammonia to 1-arylalka-1,3-dienes and 1-aryl-4-phenylbuta-1,3-dienes by photoinduced electron transfer

The photoamination of 1-arylalka-1,3-dienes 1a-f and 1-aryl-4-phenylbuta-1,3-dienes 1g-k with NH3 in the presence of p-dicyanobenzene (DCB) gives 4-amino-1-arylalk-2-enes 2a-f and 1-amino-1,4-diarylbut-2-enes 2g-k, respectively. The photoamination proceeds by nucleophilic addition of NH3 to the cation radicals of 1+. generated by photoinduced electron transfer to DCB. The regiochemistry of 2 is related to the distribution of the positive charge in 1+. calculated by the PM3-UHF/RHF method, the stability of the aminated radicals formed by the addition of NH3 to 1+. and the stability of the aminated anion formed by the reduction of the aminated radicals by DCB-.. The stabilities of these intermediates are estimated by the calculation of the heat of formation by the PM3-UHF/RHF method. Distributions of the positive charge in 1+. and the stabilities of the aminated anion show a good agreement with the product analysis.

A New Version of the Peterson Olefination Using Bis(trimethylsilyl)methyl Derivatives and Fluoride Ion as Catalyst

Reaction between a variety of bis(trimethylsilyl)methyl derivatives and carbonyl compounds under fluoride ion as catalyst is described.The reaction works especially well with nonenolizable carbonyl compounds to give the expected alkenes in high yields and, in some cases, with high stereoselectivity.Application of this methodology to an intramolecular alkenation providing a tricyclic benzocarbacephem ring system is also described.

Synthesis of Substituted 1,3-Dienes by the Reaction of Alkenylsulfonyl Chlorides with Olefins Catalyzed by a Ruthenium(II) Complex

Alkenylsulfonyl chlorides reacted with vinylarenes in the presence of a catalytic amount of dichlorotris(triphenylphosphine)ruthenium(II) to give substituted adducts, which were dehydrochlorinated and desulfonylated successively to form substituted (E,E)-1,3-dienes in good yield.

Palladium-Catalyzed Syntheses of Aryl Polyenes

The palladium-catalyzed arylation reaction has been employed to prepare a variety of mono- and diaryl 1,3-dienes and 1,3,5-trienes.The yields were good when electron withdrawing substituents were present in the aryl groups but only poor to fair when electron-donating groups were involved.Monoaryl dienes and trienes reacted well with all types of aryl halides to give mixed diaryl derivatives. 2-Bromostyrene reacts with phenylhexatriene to form 1,8-diphenyloctatetraene and with hexatriene to form 1,10-diphenyldecapentaene, but both only in about 15percent yield.