69416-93-9

Upstream product

• 106-38-7 para-bromotoluene 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 1073-67-2 4-vinylbenzyl chloride 
• 89619-10-3 1-(1-bromovinyl)-4-chlorobenzene 
• 5720-05-8 4-methylphenylboronic acid 
• 624-31-7 4-tolyl iodide 
• 637-87-6 1-Chloro-4-iodobenzene 
• 60672-33-5 4-methyl-N'-(1-(p-tolyl)ethylidene)benzenesulfonohydrazide 
• 106-44-5 p-cresol 
• 29540-83-8 p-tolyl triflate 
• 99-91-2 para-chloroacetophenone 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 106-39-8 bromochlorobenzene 
• 622-97-9 1-ethenyl-4-methylbenzene 

Downstream Products

• 28358-70-5 4-(1-(p-tolyl)vinyl)-1,1'-biphenyl 
• 5395-79-9 4'-methyl-4-chlorobenzophenone 
• 1580495-06-2 (E)-2-(2-(4-chlorophenyl)-2-(p-tolyl)vinyl)tetrahydrofuran 
• 1580495-09-5 (Z)-2-(2-(4-chlorophenyl)-2-(p-tolyl)vinyl)tetrahydrofuran 

Relevant academic research and scientific papers

Synthesis and characterization of a new zwitterionic palladium complex as an environmentally friendly catalyst for the Heck-Mizoroki coupling reaction in GVL

A new zwitterionic Palladium (II) complex has been synthesized by the one-pot mixing of Pd(OAc)2, 2-aminophenol and (3-formyl-4-hydroxy-5-methylbenzyl) triphenylphosphonium chloride, in refluxing ethanol. The metal complex formed was characterized by 1H NMR, 13C NMR, 31P NMR and X-ray crystallographic technique and its efficiency tested as a homogeneous pre-catalyst in Heck-Mizoroki cross coupling reaction using γ-Valerolactone (GVL) as a biomass-derived green medium. All the products were obtained in good to excellent yields.

Method for synthesizing alpha,beta-unsaturated selenium compound

The invention belongs to the field of organic selenium chemistry, and particularly relates to a method for synthesizing an alpha,beta-unsaturated selenium compound. The compound is synthesized by using an aryl boronic acid compound, elemental selenium and a diarylethene compound as reaction substrates. The method avoids toxic selenium-mercury reagents and toxic selenide reagents, conforms to the modern green development concept, and provides a green and economical method for synthesizing unsaturated selenium compounds in the future.

A tailored polymeric cationic tag-anionic Pd(ii) complex as a catalyst for the low-leaching Heck-Mizoroki coupling in flow and in biomass-derived GVL

The [PdCl4]2- palladium complex has been immobilized on a polystyrene-type resin loaded with pincer-type imidazolium ionic tag binding sites. The catalytic system (Pd(ii)-POLI-TAG) has proved to be highly active in the definition of an efficient protocol for the Heck-Mizoroki coupling reaction under batch and flow conditions. Importantly, it is shown to be highly robust in combination with a safe non-toxic reaction medium, i.e. biomass-derived GVL, since it could be reused for multiple runs without significantly losing its activity.

Cyrene as a Bio-Based Solvent for the Suzuki-Miyaura Cross-Coupling

The Suzuki-Miyaura (SM) cross-coupling is the most broadly utilized Pd-catalyzed C-C bond-forming reaction in the chemical industry. A large proportion of SM couplings employ dipolar aprotic solvents; however, current sustainability initiatives and increasingly stringent regulations advocate the use of alternatives that exhibit more desirable properties. Here we describe the scope and utility of the bio-derived solvent Cyrene in SM cross-couplings and evaluate its suitability as a reaction medium for this benchmark transformation from discovery to gram scale.

Branched Arylalkenes from Cinnamates: Selectivity Inversion in Heck Reactions by Carboxylates as Deciduous Directing Groups

A decarboxylative Mizoroki–Heck coupling of aryl halides with cinnamic acids has been developed in which the carboxylate group directs the arylation into its β-position before being tracelessly removed through protodecarboxylation. In the presence of a copper/palladium catalyst, both electron-rich and electron-deficient aryl bromides and chlorides bearing numerous functionalities were successfully coupled with broadly available cinnamates, with selective formation of 1,1-disubstituted alkenes. This reaction concept, in which the carboxylate acts as a deciduous directing group, ideally complements traditional 1,2-selective Heck reactions of styrenes.

Palladium-Catalyzed One-Pot Reaction of Hydrazones, Dihaloarenes, and Organoboron Reagents: Synthesis and Cytotoxic Activity of 1,1-Diarylethylene Derivatives

A new three-component assembly reaction between N-tosylhydrazones, dihalogenated arenes, and boronic acids or boronate esters was developed, producing highly substituted 1,1-diarylethylenes in good yields. The two C-C bonds formed through this coupling ha

Selective arylation and vinylation at the α position of vinylarenes

In intermolecular Heck reactions of styrene and vinylarenes, the aryl and vinyl groups routinely insert at the β position. However, selective insertion at the α position has been very rare. Herein, we provide a missing piece in the palette of Heck reaction, which gave >20:1 α selectivity. The key to our success is a new ferrocene 1,1′-bisphosphane (dnpf) that carries 1-naphthyl groups. Our mechanistic studies revealed that the high α selectivity is partly attributable to the steric effect of dnpf. The rigid and bulky 1-naphthyl groups of dnpf sterically disfavor β insertion. What the Heck! In intermolecular Heck reactions, insertion at the β position of aromatic olefins is very common, but reversal of the selectivity for selective α insertion has been a longstanding problem. A general method to couple aryl and vinyl triflates with aromatic olefins in >20:1 α selectivity is presented. The key to this successful approach is a new ferrocene bisphosphane with naphthyl groups on the phosphorus atom (see scheme; OTf=triflate). Copyright

A novel and efficient method for the olefination of carbonyl compounds with Grignard reagents in the presence of diethyl phosphite

The widely available carbonyl compounds react with Grignard reagents in the presence of diethyl phosphite to give the corresponding olefins in good to excellent yields: A range of conjugated dienes, terminal olefins, multisubstituted-alkenes and conjugated enynes could be readily obtained by the method in mild conditions.

Three phase microemulsion/sol-gel system for aqueous C-C coupling of hydrophobic substrates

Heck, Stille, Suzuki and three-component coupling reactions with hydrophobic substrates have been carried out in water. The substrates are initially transformed by a general procedure into a microemulsion, which consists of nearly 90% water with the aid of sodium dodecyl sulfate and either PrOH or BuOH. The surfactant carries the molecules of the substrates to Pd(OAc)2 entrapped within a hydrophobicitized silica sol-gel matrix where the coupling between the substrates is assumed to take place. The products are then returned by the surfactant into the microemulsion from which it can be released. The immobilized palladium catalyst is leach proof and recyclable. It can be used in various coupling processes at least six times without loss of activity. Experiments with D2O have revealed that the water does not take part in the coupling process, but it has an effect on the pore size of the sol-gel matrix, which hosts the palladium catalyst. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.