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

• 3562-73-0 1-(4-phenyl-phenyl)-1-ethanol 
• 58114-03-7 4-(1-chloroethyl)-1,1′-biphenyl 
• 917-64-6 methyl magnesium iodide 
• 134261-77-1 4-(4-Biphenylyl)-3-thiapentane-1-thiol 
• 134261-69-1 2-biphenyl-4-yl-1,3-dithiolane 
• 104586-12-1 (2-Biphenyl-4-yl-ethyl)-trimethyl-stannane 
• 74-85-1 ethene 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 87199-17-5 4-formylphenylboronic acid, 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 13116-27-3 4-iodophenylhydrazine 
• 589-87-7 1,4-bromoiodobenzene 
• 1826-67-1 vinyl magnesium bromide 
• 873869-19-3 1-(tert-butyl)-5-(methylsulfonyl)-1H-tetrazole 

Downstream Products

• 20884-11-1 4-Methoxy-4'-phenyl-stilben 
• 20883-14-1 4-Methoxy-3-nitro-4'-phenyl-stilben 
• 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 
• 92-91-1 biphenyl-4-acetaldehyde 
• 61502-90-7 4-Biphenylacetaldehyde 

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.

Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Vinyl Acetate in Dimethyl Isosorbide as a Sustainable Solvent

A nickel-catalyzed reductive cross-coupling has been achieved using (hetero)aryl bromides and vinyl acetate as the coupling partners. This mild, applicable method provides a reliable access to a variety of vinyl arenes, heteroarenes, and benzoheterocycles, which should expand the chemical space of precursors to fine chemicals and polymers. Importantly, a sustainable solvent, dimethyl isosorbide, is used, making this protocol more attractive from the point of view of green chemistry.

Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis

The value of catalytic dehydrogenation of aliphatics (CDA) in organic synthesis has remained largely underexplored. Known homogeneous CDA systems often require the use of sacrificial hydrogen acceptors (or oxidants), precious metal catalysts, and harsh reaction conditions, thus limiting most existing methods to dehydrogenation of non- or low-functionalized alkanes. Here we describe a visible-light-driven, dual-catalyst system consisting of inexpensive organophotoredox and base-metal catalysts for room-temperature, acceptorless-CDA (Al-CDA). Initiated by photoexited 2-chloroanthraquinone, the process involves H atom transfer (HAT) of aliphatics to form alkyl radicals, which then react with cobaloxime to produce olefins and H2. This operationally simple method enables direct dehydrogenation of readily available chemical feedstocks to diversely functionalized olefins. For example, we demonstrate, for the first time, the oxidant-free desaturation of thioethers and amides to alkenyl sulfides and enamides, respectively. Moreover, the system's exceptional site selectivity and functional group tolerance are illustrated by late-stage dehydrogenation and synthesis of 14 biologically relevant molecules and pharmaceutical ingredients. Mechanistic studies have revealed a dual HAT process and provided insights into the origin of reactivity and site selectivity.

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.

Illuminating Stannylation

We have developed photoboosted stannylation reactions of terminal alkynes (linear-selective hydrostannylation) and fluoroarenes (defluorostannylation), in which the stannyl anion is photoexcited to an excited triplet (T1) stannyl diradical species. This u

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.