155857-33-3

Upstream product

• 67416-43-7 1--1-phenylethene 
• 67300-99-6 1-phenylethenylmagnesium bromide 

Downstream Products

• 530-48-3 1,1-Diphenylethylene 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 718-25-2 (E)-4-fluorostilbene 
• 395-21-1 1-(4-fluorophenyl)-1-phenylethylene 
• 20488-43-1 4-acetyl-trans-stilbene 
• 87324-13-8 1-(4-(1-phenylvinyl)phenyl)ethanone 
• 4714-21-0 E-1-methyl-4-styryl-benzene 
• 948-55-0 1-phenyl-1-p-tolyl-ethylene 
• 28358-65-8 1-(1-naphthyl)styrene 
• 1149-56-0 (E)-4-trifluoromethylstilbene 
• 345-88-0 1-phenyl-1-(4-trifluoromethylphenyl)ethylene 
• 17772-45-1 1-(4-ethoxyphenyl)-2-phenylethene 
• 24638-83-3 (E)-1-(4-ethoxyphenyl)-1-phenylethene 

Relevant academic research and scientific papers

On the regioselectivity of palladium catalyzed cross-coupling reactions of alkenylsilanes: participation of β-cationic organosilicate-palladium species during the transmetallation

The cross-coupling reaction promoted by a palladium catalyst and fluoride salt of 1--1-phenylethene (1) with substituted aryl iodides gave the unexpected cine-substitution products (E)-1-aryl-2-phenylethenes (3) along with the normal ipso-substitution product 1-aryl-1-phenylethene (2).The product ratios were strongly dependent on the electronic nature of the substituent on aryl iodides: ipso-substitution products (2) were favoured by an electron-withdrawing substituent, and cine-substitution products (3) by an electron-donating substituent.On the basis of these observations, the following mechanism of transmetallation of alkenyl(fluoro)silicates with arylpalladium is proposed: electrophilic attack of an arylpalladium complex on the olefinic α-carbon of an alkenyl(fluoro)silicate produces a β-cationic organosilicate-palladium species which then transfers the alkenyl group from silicon to the palladium complex. Key words: Silane; Palladium; Transmetallation; Regioselectivity