83832-05-7

Upstream product

• 460-00-4 1-Bromo-4-fluorobenzene 
• 98-83-9 isopropenylbenzene 
• 108-86-1 bromobenzene 
• 1283231-56-0 (Z)-2-(1-(4-fluorophenyl)prop-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 18826-59-0 1-(4-fluorophenyl)-prop-1-yne 
• 1427318-37-3 C₁₆H₁₅FS 
• 676-58-4 methylmagnesium chloride 
• 1427318-06-6 C₁₀H₁₀ClFS 
• 1427317-97-2 ethyl((4-fluorophenyl)ethynyl)sulfane 
• 352-11-4 1-chloromethyl-4-fluorobenzene 
• 63909-58-0 diethyl (4-fluorobenzyl)phosphonate 
• 98-86-2 acetophenone 

Downstream Products

• 75078-91-0 (E)-1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-6-(1-methyl-2-phenylethenyl)-naphthalene 
• 58662-10-5 (E)-1-fluoro-4-(1-phenylprop-1-en-2-yl)benzene 

Relevant academic research and scientific papers

A new insight into the push-pull effect of substituents via the stilbene-like model compounds

In this paper, authors report on 1-pyridyl-2-arylethenes, 1-furyl-2-arylethylenes, 1,2-diphenylpropylenes and substituted cinnamyl anilines as stilbene-like model compounds to investigate the factors dominating the push-pull effect of substituents via usi

An operationally simple approach to (E)-α-halo vinyl sulfides and their applications for accessing stereodefined trisubstituted alkenes

An operationally simple and practical protocol for the synthesis of (E)-α-halo vinyl sulfides has been achieved via a highly regio- and stereoselective hydrohalogenation of alkynyl thioethers using lithium halides in HOAc or propionic acid at room temperature. It permits the formation of (E)-α-chloro and (E)-α-bromo vinyl sulfides in satisfactory yields with good to excellent stereoselectivities. Moreover, this work results in a new method for the assembly of stereodefined (E)- or (Z)-trisubstituted alkenes featuring the first coupling of the C-X bond of (E)-α-halo vinyl sulfides followed by a subsequent Ni-catalyzed coupling of the C-S bond with Grignard reagents. The Royal Society of Chemistry 2013.

Highly regio- and stereoselective synthesis of alkenylboronic esters by copper-catalyzed boron additions to disubstituted alkynes

The copper-catalyzed addition of bis(pinacolato)diboron to internal alkynes in the presence of methanol generates alkenylboron compounds with high levels of regio- and stereoselectivities. The catalytic efficiency is increased by using monodentate phosphine ligands, especially P(p-tolyl)3 and a range of internal alkynes was borylated in good yields. The Royal Society of Chemistry.

Phosphapalladacycle-catalyzed heck reactions for efficient synthesis of trisubstituted olefins: Evidence for palladium(0) intermediates

The coupling reaction of 1,1-disubstituted olefins (α-methyl-styrene, n-butyl methacrylate) with various aryl bromides (Heck reaction) has been studied as a new concept to synthesize trisubstituted olefins. Surprisingly, the nature of the base dramatically influences the product distribution. Thus, a systematic investigation on the role of base in Heck reactions of 1,1-disubstituted olefins was performed. Less coordinating bases like NaOAc, NaOBz or Na2CO3 yield a statistical distribution of regioisomers with the terminal olefin 10 as the major product. However, by using amines like Bu3N or diisopropylethylamine (DIPEA) as base internal olefins can be synthesized with high selectivities. With phosphapalladacycle 3 as catalyst precursor, we were able to obtain catalyst turnover numbers up to 1000, while Pd(OAc)2/2PPh3 was one order of magnitude less active. Analysis of the reaction profile by kinetic investigations led to the postulation of a reduction and subsequent oxidative addition of the catalyst precursor 3 to form 12 as catalytically active intermediate.