22057-84-7

Upstream product

• 100-42-5 styrene 
• 100-00-5 4-chlorobenzonitrile 
• 24067-17-2 4-nitrophenylboronic acid 
• 536-74-3 phenylacetylene 
• 17763-80-3 para-nitrophenyl triflate 
• 619-89-6 p-nitrocinnamic acid 
• 71-43-2 benzene 
• 22293-10-3 (1-diazoethyl)benzene 
• 586-78-7 para-nitrophenyl bromide 
• 13466-30-3 (1-phenylethylidene)hydrazine 
• 636-98-6 p-nitrobenzene iodide 
• 98-85-1 1-Phenylethanol 
• 21673-45-0 dimethyl(perfluorophenyl)(1-phenylvinyl)silane 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 

Downstream Products

• 1642593-91-6 (E)-1-nitro-4-(3,3,3-trifluoro-1-phenylprop-1-en-1-yl)benzene 
• 1144-74-7 4-nitrobenzophenone 

Relevant academic research and scientific papers

DI-, TRI- AND TETRAPHENYLINDANE DERIVATIVES AND THEIR USE IN ORGANIC ELECTRONICS

The present invention relates to indane derivatives of the formula (I) and mixtures thereof, wherein X is selected from groups of the formulae -A-NH2 or -A-(NAr2), wherein A is a chemical bond or phenylene which is unsubstituted or substituted

Radical C?H Bond Trifluoromethylation of Alkenes by High-Valent Copper(III) Trifluoromethyl Compounds

A general and selective method is developed that allows direct vinylic C?H bond trifluoromethylation of 1,1-diarylalkenes by a high-valent copper(III) trifluoromethyl complex, producing biologically active trifluoromethylated alkenes (as well as trifluoro

Overcoming Scope Limitations in Cross-Coupling of Diazo Nucleophiles by Manipulating Catalyst Speciation and Using Flow Diazo Generation

The accessible scope of palladium-catalyzed diazo cross-coupling reactions has been expanded to include aryl chlorides by controlled diazo slow addition. The success of this strategy is based on manipulating speciation within the catalytic cycle through starvation of the diazo reagent to make the Pd(II) oxidative intermediate the resting state. The strategy is also applicable to cross-coupling reactions with aryl bromides and, in combination with safe, on-demand flow generation of nonstabilized diazo reagents, has been used to greatly expand the scope of applicable diazo compounds for this chemistry as well. Lastly, DFT calculations have provided insight into the mechanism and support for the proposed explanation for success of the slow addition strategy.

SBA-15/POSS-Imidazolium Hybrid as Catalytic Nanoreactor: the role of the Support in the Stabilization of Palladium Species for C?C Cross Coupling Reactions.

Supported imidazolium modified polyhedral oligomeric silsesquioxanes (POSS) on SBA-15 have been used as platform for Pd(II) species. The so-obtained material was firstly characterized by means of TGA, solid state NMR, TEM, XPS, SAXS, porosimetry and ICP-OES and it was successfully tested as pre-catalyst in C?C cross couplings, namely Suzuki-Miyaura and Heck reactions. In both cases, the solid proved to be highly efficient and easily recoverable from the reaction mixture. The recyclability was verified for up to seven cycles without showing any activity decrease. Interestingly, only Pd(II) was detected in the reused catalyst in the Heck reaction. Therefore, the versatility of the material was investigated by using various aryl halides. Our palladium nanocomposite was able to promote both Suzuki and Heck reactions down to 0.0007 mol% showing outstanding turnover frequency (TOF) values of 114,286 and 32,381 h?1, respectively. Comparison with the palladium catalyst on SiO2-POSS-imidazolium support showed interesting differences in terms of stabilization of Pd species and recyclability. The excellent outcome of the reactions could be ascribed to the textural properties of the SBA-15 support and the presence of the imidazolium-POSS nanocage within the pores of SBA-15, that worked as a sort of nanoreactor. (Figure presented.).

Palladium nanoparticles immobilized on halloysite nanotubes covered by a multilayer network for catalytic applications

The synthesis of pure fine chemicals for industrial purposes is one of the most attractive challenges of chemical research. The use of catalytic pathways mediated by palladium nanoparticles (PdNPs) for C-C bond formation is a useful way to obtain these kinds of compounds. To achieve this objective, the PdNPs can be efficiently loaded on a functionalized natural nanostructured support such as halloysite nanotubes (HNTs). Hybrid materials based on thiol functionalized halloysite nanotubes and highly cross-linked imidazolium salts were successfully developed and used for the stabilization of PdNPs. The HNT/Pd hybrids were thoroughly characterized from a physico-chemical point of view and tested as a catalyst in the Suzuki and Heck C-C coupling reactions under microwave irradiation to obtain innovative materials for fine chemicals synthesis. Catalytic tests highlighted the fact that the HNT/Pd hybrids show high performance and full recyclability (up to ten cycles) in both reactions. Regarding the Suzuki reaction, under the best experimental conditions, the remarkable values of a turnover number of 194?000 and a turnover frequency of 3?880?000 h-1 were achieved without metal contamination in the final products.

Dehydrative Cross-Coupling of 1-Phenylethanol Catalysed by Palladium Nanoparticles Formed in situ under Acidic Conditions

A dehydrative cross-coupling of 1-phenylethanol catalysed by sugar derived, in situ formed palladium(0) nanoparticles under acidic conditions is realised. The acidic conditions allow for use of alcohols as a feedstock in metal-mediated coupling reactions via their in situ dehydration and subsequent cross-coupling. Extensive analysis of the size and morphology of the palladium nanoparticles formed in situ showed that the zero-valent metal was surrounded by hydrophilic hydroxyl groups. EDX-TEM imaging studies using a prototype silicon drift detector provided insight into the problematic role of molecular oxygen in the system. This increased understanding of the catalyst deactivation allowed for the development of the cross-coupling methodology. A 250-12,000 fold increase in molar efficiency was observed when compared to related two-step protocols that use alternative feedstocks for the palladium-mediated synthesis of stilbenes. This work opens up a new research area in which the active catalyst is formed, stabilised and regenerated by a renewable sugar.

Traceless directing group mediated branched selective alkenylation of unbiased arenes

Owing to the synthetic importance of branched olefinated products, we report palladium catalyzed formation of branched olefins facilitated by a C-H activation based protocol. This involves selective insertion of olefins and subsequent decarboxylation using a completely unbiased benzene ring as the starting precursor. The significance of the protocol has been further highlighted by exhibition of functionality tolerance along with a late-stage modification of the branched olefinated products leading to the formation of other functionalized molecules.

Immobilized palladium nanoparticles on potassium zirconium phosphate as an efficient recoverable heterogeneous catalyst for a clean Heck reaction in flow

Palladium nanoparticles on layered potassium α-zirconium phosphate (PdNP/α-ZrPK) with high palladium loading (10.6 wt%) have been prepared and used as catalyst in low amount (0.1 mol% of Pd) in the Heck reaction of methyl acrylate and styrene with a series of aryl iodides in CH3CN/H2O azeotrope as a green medium. The procedure has been optimized under flow conditions obtaining an extremely low waste production (E-factor) and allowing to isolate the final product with very low residual palladium content without any purification step.

Olefin Preparation via Palladium-Catalyzed Oxidative De-Azotative and De-Sulfitative Internal Cross-Coupling of Sulfonylhydrazones

A novel reactivity of sulfonylhydrazones under Pd catalysis is described, where SO2 and N2 are formally extruded to afford the product of an apparent internal coupling reaction. The reaction is effective with both carbocyclic and heterocyclic aromatic precursors.

Direct C-H trifluoromethylation of di- and trisubstituted alkenes by photoredox catalysis

Background: Trifluoromethylated alkene scaffolds are known as useful structural motifs in pharmaceuticals and agrochemicals as well as functional organic materials. But reported synthetic methods usually require multiple synthetic steps and/or exhibit lim