2350-89-2

Usage

Uses

4-Vinylbiphenyl intermediate is used in organic synthesis and in chemical research.

InChI:InChI=1/C14H12/c1-2-12-8-10-14(11-9-12)13-6-4-3-5-7-13/h2-11H,1H2

Upstream product

• 58114-03-7 4-(1-chloroethyl)-1,1′-biphenyl 
• 74-85-1 ethene 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 98-80-6 phenylboronic acid 
• 87199-17-5 4-formylphenylboronic acid, 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 13116-27-3 4-iodophenylhydrazine 
• 873869-19-3 1-(tert-butyl)-5-(methylsulfonyl)-1H-tetrazole 
• 3218-36-8 4-Phenylbenzaldehyde 
• 71844-24-1 p-biphenyldiazoethane 
• 925-93-9 ethyl [2]alcohol 
• 7459-73-6 (4-Vinylphenyl)magnesium chloride 
• 16532-02-8 bromomethyldimethylsilyl chloride 

Downstream Products

• 263-06-9 6H,12H-Dibenzo<1,5>dithiocin 
• 120229-37-0 3,4-Dihydro-2-(4-biphenylyl)-2H-1-benzothiopyran 
• 120229-46-1 3,4-Dihydro-3-(4-biphenylyl)-2H-1-benzothiopyran 
• 36099-26-0 2-([1,1′-biphenyl]-4-yl)oxirane 
• 438590-52-4 dimethyl 6-[(E)-2-[1,1'-biphenyl-4-yl]ethenyl]quinoline-2,4-dicarboxylate 
• 59908-88-2 2-([1,1'-biphenyl]-4-yl)-propanal 
• 75677-09-7 3-([1,1′-biphenyl]-4-yl)propanal 
• 950505-77-8 (R/S)-[6-((E)-2-biphenyl-4-yl-vinyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-acetic acid ethyl ester 
• 950505-78-9 (R/S)-[6-(1-biphenyl-4-yl-vinyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-acetic acid ethyl ester 
• 115290-43-2 (1-phenyl-2-(p-phenylphenyl)phosphirane)pentacarbonyltungsten 

Relevant academic research and scientific papers

Nickel-catalyzed vinylation of aryl chlorides and bromides with vinyl ZnBr · MgBrCl

The Ni-catalyzed cross-coupling of aryl halides and vinylzinc bromide for the synthesis of styrene derivatives was investigated. Of the catalysts surveyed, the combination of Ni(acac)2 and Xantphos was found to be the most effective for this cr

Hexacationic Dendriphos ligands in the Pd-catalyzed Suzuki-Miyaura cross-coupling reaction: Scope and mechanistic studies

The combination of Pd2dba3·CHCl3 and hexacationic triarylphosphine-based Dendriphos ligands (1-3) leads to a highly active catalytic system in the Suzuki-Miyaura cross-coupling reaction. Under relatively mild reaction conditions, nonactivated aryl bromides and activated aryl chlorides can be coupled at a low Pd loading (0.1 mol %). The observed activity of this catalytic system, in particular in coupling reactions of aryl chlorides, is dramatically higher than that of conventional Pd catalysts employing triarylphosphine ligands. Through control and poisoning experiments, it is concluded that a homogeneous Pd(0)-Dendriphos complex is the active species in this catalytic system. Despite their triarylphosphine-based structure, Dendriphos ligands behave as very bulky phosphine ligands and lead to a preferential formation of coordinatively unsaturated and catalytically active Pd(0) species, which explains the observed high catalytic activity for these systems. The presence of six permanent cationic charges in the backbone of this class of ligands is proposed to result in a significant interligand Coulombic repulsion and plays a crucial role in their bulky behavior. In the coupling reactions of activated aryl chlorides, a positive dendritic kinetic effect was observed among the different Dendriphos generations, indicating an increased ability of the higher ligand generations to stabilize the active species due to steric effects. For aryl bromides, no dendritic effect was observed due to a shift in the rate-determining step in the catalytic cycle, from oxidative addition for aryl chlorides to transmetalation for aryl bromides.

Functionalized styrene synthesis via palladium-catalyzed C[sbnd]C cleavage of aryl ketones

We report herein the synthesis of functionalized styrenes via palladium-catalyzed Suzuki–Miyaura cross-coupling reaction between aryl ketone derivatives and potassium vinyltrifluoroborate. The employment of pyridine-oxazoline ligand was the key to the cleavage of unstrained C[sbnd]C bond. A variety of functional groups and biologically important moleculars were well tolerated. The orthogonal Suzuki–Miyaura coupling demonstrated the synthetic practicability.

Palladium-Catalyzed Tail-to-Tail Reductive Dimerization of Terminal Alkynes to 2,3-Dibranched Butadienes

The palladium-catalyzed tail-to-tail reductive dimerization of terminal alkynes is described for the first time. Aromatic terminal alkynes bearing diverse and sensitive functional groups as well as aliphatic terminal alkynes are efficiently transformed to 2,3-dibranched butadienes. The key to achieve a selective tail-to-tail reductive dimerization reaction is to control appropriately the acidity of the reaction solution, which is accomplished by a combined use of pivalic acid and para-toluenesulfonic acid. The tail-to-tail reductive dimerization reaction is proposed to proceed via a cationic alkenyl palladium intermediate under acidic conditions.

Activation of Aryl Carboxylic Acids by Diboron Reagents towards Nickel-Catalyzed Direct Decarbonylative Borylation

The Ni-catalyzed decarbonylative borylation of (hetero)aryl carboxylic acids with B2cat2 has been achieved without recourse to any additives. This Ni-catalyzed method exhibits a broad substrate scope covering poorly reactive non-ortho-substituted (hetero)aryl carboxylic acids, and tolerates diverse functional groups including some of the groups active to Ni0 catalysts. The key to achieve this decarbonylative borylation reaction is the choice of B2cat2 as a coupling partner that not only acts as a borylating reagent, but also chemoselectively activates aryl carboxylic acids towards oxidative addition of their C(acyl)?O bond to Ni0 catalyst via the formation of acyloxyboron compounds. A combination of experimental and computational studies reveals a detailed plausible mechanism for this reaction system, which involves a hitherto unknown concerted decarbonylation and reductive elimination step that generates the aryl boronic ester product. This mode of boron-promoted carboxylic acid activation is also applicable to other types of reactions.

Method for reducing alkyne into olefin by taking water as hydrogen source under catalysis of nickel

The invention discloses a method for reducing alkyne into olefin by taking water as a hydrogen source under the catalysis of nickel, which comprises the following steps: placing alkyne in a solvent to react under the action of a nickel catalyst, a ligand, alkali, a boron reagent and a hydrogen source, and carrying out post-treatment to obtain olefin, and the hydrogen source is water. According to the invention, a cheap metal nickel catalyst is combined with a boron reagent to activate water, so that hydrogen transfer is realized, and the use of dangerous hydrogen is avoided. The method has good stereoselectivity, no excessive hydrogenation product alkane is generated, conditions are mild, the highest yield can reach 99%, and the method has good application prospects.

Electrochemical fluorosulfonylation of styrenes

An environmentally friendly and efficient electrochemical fluorosulfonylation of styrenes has been developed. With the use of sulfonylhydrazides and triethylamine trihydrofluoride, a diverse array of β-fluorosulfones could be readily obtained. This reaction features mild conditions and a broad substrate scope, which could also be conveniently extended to a gram-scale preparation.

Electrochemistry enabled selective vicinal fluorosulfenylation and fluorosulfoxidation of alkenes

Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation and fluorosulfoxidation reactions of alkenes, which were enabled by the unique ability of electrochemistry to dial in the potentials on demand. Preliminary mechanistic investigations revealed that the fluorosulfenylation reaction proceeded through a radical-polar crossover mechanism involving a key episulfonium ion intermediate. Subsequent electrochemical oxidation of fluorosulfides to fluorosulfoxides were readily achieved under a higher applied potential with the adventitious H2O in the reaction mixture.

Zinc salt-catalyzed reduction of α-aryl imino esters, diketones and phenylacetylenes with water as hydrogen source

The zinc salt-catalyzed reduction of α-aryl imino esters, diketones and phenylacetylenes with water as hydrogen source and zinc as reductant was successfully conducted. The presented method provides a low-cost, environmentally friendly and practical preparation of α-aryl amino esters, α-hydroxyketones and phenylethylenes. By using D2O as deuterium source, the corresponding products were obtained in high efficiency with excellent deuterium incorporation rate, which gives a cheap and safe tool for access to valuable deuterium-labelled compounds. This journal is

Chemodivergent Synthesis of One-Carbon-Extended Alcohols via Copper-Catalyzed Hydroxymethylation of Alkynes with Formic Acid

The development of selective catalytic reactions that utilize easily available reagents for the efficient synthesis of alcohols is a long-standing goal of chemical research. Here an intriguing strategy for the chemodivergent copper-catalyzed hydroxymethylation of alkynes with formic acid and hydrosilane has been developed. By simply tuning the amount of formic acid and reaction temperature, distinct one-carbon-extended primary alcohols, that is, allylic alcohols and β-branched alkyl alcohols, were produced with high levels of Z/E-, regio-, and enantioselectivity.